Polarizing electrochromic medium

Abstract

An electro-optic element includes a cathodic compound and an anodic compound. At least one of the cathodic compound and the anodic compound include a homochiral functional group that is in close proximity to a corresponding optical transition dipole of one of the cathodic compound and the anodic compound. The electro-optic medium is configured to reversibly generate a dichroic absorbance in the visible spectrum.

Description

POLARIZING ELECTROCHROMIC MEDIUMCROSS-REFERENCE TO RELATED APPLICATION

[0001] This application claims priority to and the benefit under 35 U.S.C. § 119(e) of U.S. Provisional Patent Application No. 63 / 675,581, filed on July 25, 2024, entitled "POLARIZING ELECTROCHROMIC MEDIUM," by Zachary B. Erno and Jerod M. Kieser, the entire disclosure of which is incorporated herein by reference.TECHNICAL FIELD

[0002] The present disclosure generally relates to polarizing electrochromic mediums, and more particularly to electrochromic mediums including chiral electrochromic compounds.SUMMARY

[0003] According to one aspect of the present disclosure, an electro-optic element includes a cathodic compound and an anodic compound. At least one of the cathodic compound and the anodic compound includes a homochiral functional group in close proximity to a corresponding optical transition dipole of one of the cathodic compound and the anodic compound. The medium is configured to reversibly generate a dichroic absorbance in the visible spectrum.

[0004] According to another aspect of the present disclosure, a cathodic medium for an electro-optic element, may include a chemical compound of Formula (I) or (II) or (III):orwherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

[0005] According to another aspect of the present disclosure, the anodic compound is a chemical compound of Formula (IV) or (V):wherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

[0006] According to yet another aspect of the present disclosure, a medium for electro-optic element includes a cathodic compound and an anodic compound, wherein the cathodic compound and the anodic compound are dissolved into an electrolyte solvent, the electrolytesolvent including a homochiral functional group, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

[0007] According to yet another aspect of the present disclosure, a medium for an electrooptic element includes a cathodic compound and an anodic compound, wherein at least one of the cathodic compound and the anodic compound comprise a homochiral functional group 1.5-10 A away from a corresponding optical transition dipole of the one of the cathodic compound and the anodic compound, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

[0008] These and other features, advantages, and objects of the present disclosure will be further understood and appreciated by those skilled in the art by reference to the following specification, claims, and appended drawings.BRIEF DESCRIPTION OF THE DRAWINGS

[0009] In the drawings:

[0010] FIG. 1A illustrates a cross-sectional schematic view of an electro-optic element according to aspects of the present disclosure;

[0011] FIG. IB illustrates a cross-sectional schematic view of an electro-optic element according to aspects of the present disclosure;

[0012] FIG. 2A illustrates a schematic view of the chemical structure of an exemplary anodic element according to an aspect of the present disclosure;

[0013] FIG. 2B illustrates a schematic view of the chemical structure of an exemplary anodic element according to an aspect of the present disclosure;

[0014] FIG. 3A illustrates a schematic view of the chemical structure of an exemplary cathodic element according to an aspect of the present disclosure;

[0015] FIG. 3B illustrates a schematic view of the chemical structure of an exemplary cathodic element according to an aspect of the present disclosure;

[0016] FIG. 3C illustrates a schematic view of the chemical structure of an exemplary cathodic element according to an aspect of the present disclosure;

[0017] FIG. 4A illustrates a schematic view of the chemical structure of an exemplary chemical moiety according to an aspect of the present disclosure;

[0018] FIG. 4B illustrates a schematic view of the chemical structure of an exemplary chemical moiety according to an aspect of the present disclosure;

[0019] FIG. 4C illustrates a schematic view of the chemical structure of an exemplary chemical moiety according to an aspect of the present disclosure;

[0020] FIG. 4D illustrates a schematic view of the chemical structure of an exemplary chemical moiety according to an aspect of the present disclosure;

[0021] FIG. 4E illustrates a schematic view of the chemical structure of an exemplary chemical moiety according to an aspect of the present disclosure;

[0022] FIG. 4F illustrates a schematic view of the chemical structure of an exemplary chemical moiety according to an aspect of the present disclosure; and

[0023] FIG. 4G illustrates a schematic view of the chemical structure of an exemplary chemical moiety according to an aspect of the present disclosure.DETAILED DESCRIPTION

[0024] The present illustrated embodiments reside primarily in combinations of method steps and apparatus components related to chiral electrochemical compounds as components for electro-optic elements and electro-optic mediums, as discussed below. Accordingly, the apparatus components and method steps have been represented, where appropriate, by conventional symbols in the drawings, showing only those specific details that are pertinent to understanding the embodiments of the present disclosure so as not to obscure the disclosure with details that will be readily apparent to those of ordinary skill in the art having the benefit of the description herein. Further, like numerals in the description and drawings represent like elements.

[0025] As used herein, the term "and / or," when used in a list of two or more items, means that any one of the listed items can be employed by itself, or any combination of two or more of the listed items, can be employed. For example, if a composition is described as containingcomponents A, B, and / or C, the composition can contain A alone; B alone; C alone; A and B in combination; A and C in combination; B and C in combination; or A, B, and C in combination.

[0026] In this document, relational terms, such as first and second, top and bottom, and the like, are used solely to distinguish one entity or action from another entity or action, without necessarily requiring or implying any actual such relationship or order between such entities or actions. The terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. An element proceeded by "comprises ... a" does not, without more constraints, preclude the existence of additional identical elements in the process, method, article, or apparatus that comprises the element.

[0027] Referring to FIGS. 1-4G, reference numeral 10 generally designates an electro-optic element including an electrochromic medium 14. The electrochromic medium 14 includes a cathodic compound 18 and an anodic compound 22. At least one of the cathodic compound 18 and the anodic compound 22 includes a homochiral functional group 26 that is in close proximity to a corresponding optical transition dipole. The electrochromic medium 14 is configured to absorb circularly polarized light in the visible spectrum.

[0028] Aspects of the present disclosure relate to electrochromic compounds containing chirality, and, more particularly, to homochiral functional groups 26 coupled to electrochromic compounds as components for electro-optic elements 10 and electrochromic mediums 14. The chiral electrochromic compounds of the present disclosure can be used in electro-optic elements 10 and electrochromic devices 28 incorporating such electro-optic elements. By way of introduction, electrochromic devices 28 generally include an electrochromic medium 14 that transitions between an inactivated state in which the electrochromic medium 14 is relatively transparent to light having a wavelength within a predetermined wavelength range and an activated state in which the electrochromic medium 14 has a decreased transmission to light within a predetermined wavelength range when an electrical potential is applied to the electrochromic device 28. The electrochromic medium 14includes an anodic component (e.g., the anodic compound 22) and a cathodic component (e.g., the cathodic compound 18), which may also be referred to as electroactive components, at least one of which is also electrochromic. The anodic and cathodic components 22, 18, respectively, may, alternatively, be referred to as chromophores, electrochromic moieties, molecules or dyes, or electrochromic polymers. The electrochromic and / or electroactive component can provide the electrochromic device 28 with a perceived color when the electrochromic device is in the activated state and / or as the device transitions between the inactivated and activated states.

[0029] The term "electroactive," as used herein, refers to a material that can undergo a modification in its oxidation state upon exposure to a particular electrical potential difference. The term "electrochromic," as used herein, refers to a material that can exhibit a change in its extinction coefficient at one or more wavelengths upon exposure to a particular electrical potential difference. Electrochromic components, as described herein, include materials whose color or opacity is affected by an electrical current, such that when an electrical field is applied to the material, the color or opacity changes from a first state to a second state (e.g., the inactivated and activated states). Thus, an electrochromic device can exhibit a change in transparency as a result of electrochemical oxidation and reduction reactions that occur between electroactive components (e.g., the anodic components and the cathodic components), in which at least one of the electroactive components is also electrochromic. In other words, when a sufficient electrical potential difference is applied across electrodes of an electrochromic device, the electrochromic medium can shift from a substantially clear state (e.g., a high transmission state, such as the inactivated state) to a substantially dark or darkened state (e.g., a low transmission state, such as the activated state), as well as intermediate states thereto, in the event that one or more of the anodic and the cathodic components are oxidized and reduced, respectively. Specifically, the anodic components are oxidized by donating electrons to the anode and the cathodic components are reduced by accepting electrons from the cathode. Accordingly, the anodic compound, refers to a compound that can reversibly lose an electron(s) upon activation and the cathodic compound, as used herein, refers to a compoundthat can reversibly gain an electron(s). Non-limiting examples of anodic compounds include 5,10-Dihydro-5,10-dialkylphenazines, 10-alkylphenothiazine, ferrocene and derivatives thereof, triphenylamine (TPA) derivatives, vanadium-titanium oxide (VTiOx), metallocenes, dihydrophenazines, 5,10-dihydrophenazines, phenoxazines, carbazoles, triphenodithiazines, triphenodioxazines, substituted ferrocenes, phenazine, substituted phenazines, phenothiazine, substituted phenothiazines, substituted dithiazines, thianthrene and substituted thianthrenes, di-tert-butyl-diethylferrocene, 5,10-dimethyl-5,10- dihydrophenazine (DMP), 3,7,10-trimethylphenothiazine, 2,3,7,8-tetramethoxy-thianthrene, 10-methylphenothiazine, tetramethylphenazine (TMP), bis(butyltriethylammonium)-para- methoxytriphenodithiazine (TPDT), 3,10-dimethoxy-7,14-(triethylammoniumbutyl)- triphenodithazinebis(tetrafluoroborate), nickel containing oxides, and combinations thereof. Non-limiting examples of cathodic compounds include l,l'-dialkyl-4,4'-bipyridiniums (viologens), substituted viologens, low-dimerizing viologens, substituted low-dimerizing viologens, non-dimerizing viologens or substituted non-dimerizing viologens, ferrocenium, poly dioxythiophenes, tungsten oxides (WOX) and derivatives thereof,.

[0030] Referring now to FIG. 1A, an exemplary electro-optic element 10 including an electrochromic medium 14 including both of the anodic compounds 22 and cathodic compounds 18 is illustrated. As illustrated, the electrochromic medium 14 is disposed between a first electrically conductive layer 30 and a second electrically conductive layer 32. In one example, one or both of the chromophores may be in solution and able to diffuse between the adjacent electrode and an opposing electrode as shown in FIG 1A.

[0031] Referring now to FIG. IB, another exemplary electro-optic element 10 is illustrated. As illustrated in FIG. IB, a cathodic film 36 is disposed on the first electrically conductive layer 30 and an anodic film 40 is disposed on the second electrically conductive layer 32. An electrolyte layer 44 is provided between the cathodic film 36 and the anodic film 40. In some implementations, in the case where the electro-optic element 10 is in the form of a bi-stable device, both sets of chromophores (cathodic and anodic moieties) may be attached to their respective electrodes. A bi-stable device may include a device with two active states whichcan be considered thermodynamically stable, as in each state may be considered resting without the need for further input.

[0032] While aspects of the present disclosure are described in the context of the electrooptic element 10, aspects of the present disclosure may also be utilized in the context of other electrochromic or electro-optic devices. Non-limiting examples of which include bi-stable devices, circular polarizing devices, dimmable and polarizing eyewear, helmet visors, vanity mirrors-in-visors, switchable 3D eyewear, switchable mirrors, switchable and / or rotatable polarizers for cameras, transflective windows and / or displays, and switchable reflector full display mirrors.

[0033] Referring to FIGS. 1A-B, the electro-optic element 10 can include a first substrate 48 having a first surface 52 and a second surface 54. The first electrically conductive layer 30 is disposed on the second surface 54. A second substrate 58 is provided opposite the first substrate 48 and includes a third surface 62 and a fourth surface 66. The second electrically conductive layer 32 is disposed on the third surface 62. The first substrate 48 and the second substrate 58, along with a sealing member 70 define a chamber 74 for containing the electrochromic medium 14 therein.

[0034] The electro-optic element 10 allows the electrochromic device 28 to be operable between a first state of the electro-optic element 10, which allows electromagnetic radiation having a wavelength within a predetermined wavelength range to pass through, and a second state, in which a portion, or no electromagnetic radiation having a wavelength within a predetermined wavelength range, is transmitted through the electro-optic element 10 (e.g., the electro-optic element 10 becomes generally opaque or partially opaque to electromagnetic radiation having a wavelength within the predetermined wavelength range). The second state of the electro-optic element 10 can be defined relative to the transmissivity of the first state. According to an aspect of the present disclosure, the transmissivity of electromagnetic radiation of a predetermined wavelength or wavelength range through the electro-optic element 10 in the first state may be greater than about 10%, greater than about 12%, greater than about 25%, greater than about 50%, greater than about 55%, or greater than about 85%. In specific implementations, the transmissivity values may be higher than50%, such as in a range of approximately 60-70%. It is noted that transmission of one handedness of circular polarized light may include transmissivity in a range of 15% or less, 10% or less, 5% or less, etc. Typically, the percentage of reflectance, transmittance, and absorbance of the electro-optic element 10 sum to 100%. In some aspects, the transmissivity of electromagnetic radiation of the predetermined wavelength or wavelength range through the electro-optic element 10 in the substantially second state may be less than about 10%, less than about 1%, less than about 0.1%, less than about 0.01%, or less than about 0.001%.

[0035] The first and / or second substrates 48, 58 can be made of glass, plastic, or other optically transparent or translucent material(s), non-limiting examples of which include borosilicate glass, soda lime glass, or polymeric materials, such as natural and synthetic polymeric resins, plastics, and / or composites. Non-limiting examples of such include polyesters (e.g., PET), polyimides (PI), polycarbonates, polysulfones, polyethylene naphthalate (PEN), ethylene vinyl acetate (EVA), acrylate polymers, as well as cyclic olefin copolymers (COC) and cyclic olefin polymers (COP) (such as those commercially available from TOPAS® Advanced Polymers). In some aspects, both the first and second substrates 48, 58 are made of an optically transparent or translucent material, while, in other aspects, only a single substrate, such as the first substrate 48, is made of an optically transparent or translucent material. The first and second substrates 48, 58 can be made from the same or different materials and may have the same or different dimensions.

[0036] The first and second electrically conductive layers 30, 32 can include one or more layers of an electrically conductive material disposed on the first and second substrates 48, 58, respectively. These layers serve as electrodes (e.g., the cathode and the anode) for the electro-optic element 10. The electrically conductive material(s) of the first and / or second electrically conductive layers 30, 32 may be any suitable material that includes one or more of the following features: (a) substantially transparent to electromagnetic radiation in the visible and / or infrared wavelength ranges; (b) bonds reasonably well to the first and second substrates 48, 58; (c) maintains the bond to the first and second substrates 48, 58 when associated with the sealing member 70; (d) generally resistant to corrosion from materials contained within the electrochromic device 28 orthe atmosphere; and / or (e) exhibits minimaldiffuse or specular reflectance as well as sufficient electrical conductance. Depending on the application, only one of the first and second electrically conductive layers 30, 32 may be required to be transparent while the other electrically conductive layer 30, 32 may be opaque. In some applications, both the first and the second electrically conductive layers 30, 32 may be transparent. According to some aspects, one of the first and second electrically conductive layers 30, 32, such as the second electrically conductive layer 32, may include a metal reflector or one or more coatings configured as a partially reflective, partially transmissive ("transflective") coating. Inclusion of a metal reflector or a transflective coating may render the electrochromic device at least partially reflective. Accordingly, the electrically conductive material(s) forming the first and second electrically conductive layers 30, 32 may be the same or different. Non-limiting examples of electrically conductive material that may be used to form the first and / or second electrically conductive layers 30, 32 can include transparent conductive oxides (TCOs) such as fluorine doped tin oxide (FTO), for example TEC™ glass, indium tin oxide (ITO), doped zinc oxide, indium zinc oxide (IZO), aluminum doped zinc oxide (AZO), metal oxide / metal / metal oxide (including, where the metal oxide can be substituted with metal carbide, metal nitride, metal sulfide, etc.), nanowires, wire mesh, and carbon based conductors.

[0037] Referring to the exemplary electrochromic device 28 illustrated in FIG. 1A, the sealing member 70 can traverse, or extend along, and cooperate with an approximate perimeter of, the first and second substrates 48, 58 to define the chamber 74 as substantially hermetic. The sealing member 70 may be disposed around a perimeter of the electrochromic medium 14 (e.g., extending from the second surface 54 to the third surface 62). The sealing member 70 may be in the form of any suitable seal type and material. For example, the sealing member 70 may include thermoset epoxy.

[0038] In some examples, first and second annular bands of highly conductive material are optionally deposited around the perimeter of the first and second substrates 48, 58, respectively, and electrically-conducting structures 88 (e.g., conductive tape, clips, traces, or wires) are secured to the highly conductive material and spatially separated from one another. The electrically-conducting structures 88 may supply an electrical voltage to the firstand second annular bands of highly conductive material to create a voltage across the electrooptic element 10, thereby reversibly driving the electro-optic element 10 between states, such as the substantially dark and substantially clear states. The first and second annular bands of highly conductive material may include silver, gold, copper, or aluminum (such as, for example, in a form of metallic flakes or particles dispersed in a hosting material).

[0039] The electro-optic element 10 includes the electrochromic medium 14. The electrochromic medium 14 includes at least one of the cathodic compounds 18 and at least one of the anodic compounds 22. According to the present disclosure, the anodic and / or cathodic compounds may be a polymer. Optionally, the anodic and / or cathodic components may be dissolved in an electrochemical solvent as further discussed below. In some aspects, both the cathodic and anodic components are electroactive and at least one of the anodic component or cathodic component is electrochromic.

[0040] The components of the electrochromic medium 14 can be utilized in film form (e.g., a solid polymer or a gel polymer), gel form, or solution form in the electro-optic element 10. FIG. 1A illustrates an electrochromic medium 14 which may be in gel form or solution form. Accordingly, the chromophores may be incorporated into a polymer gel or dissolved into an electrochemical solvent or electrolyte solvent. In film examples, such as the example illustrated in FIG. IB, the electrochromic medium 14 may include one or more layers of material(s) attached directly to an electrically conductive layer (e.g., 30, 32) or confined in close proximity to an electrically conductive layer (e.g., 30, 32), which remains attached or confined when components thereof are oxidized and / or reduced. However, aspects of the present disclosure can be applicable to any suitable electrochromic medium 14 utilized with the electro-optic element 10, such as a full film device. In such an example, an electro-optic film may contain both the anodic compound 22 and the cathodic compound 18 on the backbones of a polymeric chain, and / or as pendant groups.

[0041] As illustrated in FIG. IB, the electrochromic medium 14 utilized with the electro-optic element 10 includes both a cathodic film 36 and an anodic film 40. The electrolyte layer 44 separates the cathodic and anodic films 36, 40. In this way, the cathodic film 36, anodic film 40, and electrolyte layer 44 define the electrochromic medium 14. In one embodiment, thecathodic film 36 may contain the cathodic compound 18 on the backbone of the polymeric chains, and / or as pendant groups (e.g., side chain modifications), while the anodic film 40 may contain the anodic compound 22 on the backbone of the polymeric chains, and / or as pendant groups. When the electro-optic element 10 is formed, the cathodic film 36 can be adjacent to the electrolyte layer 44 and does not substantially permeate into the electrolyte layer 44 as it is immobile on the first electrically conductive layer 18. Likewise, when the electro-optic element 10 is formed, and the anodic film 40 can be adjacent to the electrolyte layer 44 and does not permeate into the electrolyte layer 44 as it is immobile on the second electrically conductive layer 32.

[0042] The electrolyte layer 44 may be a gel (e.g., a semi-liquid configured to permeate the cathodic and anodic films 36, 40) or a polymeric electrolyte configured as a thin film electrolyte. In examples utilizing a polymeric electrolyte in the electrochromic medium 14, the polymeric electrolyte may include a polymer, such as polymethyl methacrylate ("PM MA"), poly(styrene-ran-ethylene), polystyrene-b / ock-poly(ethylene-ran-butylene), poly(styrene-ran-ethylene), polystyrene-b / ock-poly(ethylene / butylene)-b / ock-polystyrene, polyfethylene glycol), polyfmethyl acrylate), other polymer electrolytes and / or combinations thereof and various plasticizers, such as propylene carbonate, ethylene carbonate, dimethyl carbonate, and the like. In some examples the electrolyte layer 44, including plasticizers associated therewith, may partially permeate the cathodic and anodic films 36, 40.

[0043] The anodic compound 22 of the electrochromic medium 14 can include one or more anodic components or moieties. Non-limiting examples of anodic components include triphenyl amines (TPAs), vanadium-titanium oxide (VTiOx), metallocenes, 5,10- dihydrophenazines, phenoxazines, carbazoles, triphenodithiazines, triphenodioxazines, ferrocene, substituted ferrocenes, phenazine, substituted phenazines, phenothiazine, substituted phenothiazines, substituted dithiazines, thianthrene and substituted thianthrenes, di-tert-butyl-diethylferrocene, 5,10-dimethyl-5,10-dihydrophenazine (DMP), 3,7,10-trimethylphenothiazine, 2,3,7,8-tetramethoxy-thianthrene, 10-methylphenothiazine, tetramethyl phenazine (TMP), bis(butyltriethylammonium)-para-methoxytri phenodithiazine(TPDT), 3,10-dimethoxy-7,14-(triethylammoniumbutyl)- triphenodithazinebis(tetrafluoroborate), nickel containing oxides and combinations thereof.

[0044] The cathodic compound 18 of the electrochromic medium 14 can include one or more cathodic components or moieties, which can include a reducible compound. Non-limiting examples of cathodic components include viologens, substituted viologens, poly dioxythiophenes, tungsten oxides (WOX), low-dimerizing viologens, substituted low- dimerizing viologens, non-dimerizing viologens or substituted non-dimerizing viologens. Illustrative viologens include, but are not limited to, methyl viologen, octyl viologen, benzyl viologen, polymeric viologens, and the viologens described in U.S. Pat. Nos. 4,902,108; 6,188,505; 5,998,617; 9,964,828; 10,481,456; and 6,710,906, which are herein incorporated by reference in their entirety. In one aspect, the cathodic component is a viologen, a low- dimerizing viologen, a non-dimerizing viologen, a substituted viologen, a di-acrylate viologen, a cathodic di-vinyl viologen, a cathodic di-vinyl ether viologen, a cathodic di-epoxy viologen, a cathodic di-oxetane viologen, a cathodic di-hydroxy viologen, or a combination thereof. In some examples, the electrochromic medium may include a combination of two or more cathodic components to provide the electrochromic medium 14 with a desired color when activated. Examples of suitable combinations of anodic and cathodic components can be found in U.S. Patent No. 6,020,987, entitled "Electrochromic Medium Capable of Producing a Pre-Selected Color," issued February 1, 2000, the contents of which are incorporated herein by reference in its entirety.

[0045] The electrolyte layer 44 of the electrochromic medium 14 as in FIG. IB, or the electrochromic medium 14 as in FIG. 1A may also include one or more electrolytes, which may be in the form of a solvent and a salt. The salt may be a metal salt or an ammonium salt. Nonlimiting examples of suitable solvents for use in the electrolyte include: 3-methylsulfolane, dimethyl sulfoxide, dimethyl formamide, tetraglyme, and other polyethers; alcohols, such as ethoxyethanol; nitriles, such as acetonitrile, glutaronitrile, 3-hydroxypropionitrile, and 2- methylglutaronitrile; ketones, including 2-acetylbutyrolactone and cyclopentanone; cyclic esters including beta-propiolactone, gamma-butyrolactone, and gamma-valerolactone; carbonate esters including propylene carbonate (PC) and ethylene carbonate; andhomogenous mixtures thereof. Non-limiting examples of suitable salts include: metal or ammonium salts, such as lithium triflate, lithium perchlorate, sodium triflate, sodium perchlorate, etc., Li+, Na+, K+, NR (where each R' is individually H, alkyl, or cycloalkyl), or the following anions F", Cl", Br", I", BF4", PFe ", SbFe ", AsFe", CIOzT, SC CFs", NfCFsSChh", CfCFsSChh ", N(SO2C2F5)2", AI(OC(CF3)3)4", or BAu", where Ar is an aryl or fluorinated aryl group such as, but not limited to, CeHs, 3,5-(CF3)2CeH3, or CeFs.

[0046] Referring now to FIGS. 2A-3C, aspects of the present disclosure relate to formulating chiral electroactive compounds. The electro-optic elements 10 can include the chiral electroactive compounds coupled with at least one of the cathodic and anodic compounds 18, 22, that are configured to absorb circularly polarized light in the visible spectrum. In some aspects, the electrochromic medium 14 can reversibly generate a dichroic absorbance in the visible wavelength region using solution-phase molecules. Recent research efforts toward electrochromic device design have led to a desire to fabricate such devices that in the darkened state would exhibit circular dichroic behavior of the visible spectrum, and, while in the clear state, the devices would permit both polarized and non-polarized light to pass through. Specifically, the polarizing molecules (e.g., cathodic and anodic compounds 18, 22) include chirality of left or right handedness. The polarization or dichroism property is turned on as power is applied to the device 28. In some aspects, a single device 28 can either absorb one circular polarization or the other and go from high end transmission of greater than 50% when the device 28 is not darkened to a much lower end transmission as the device 28 becomes absorbing, with a biased absorption towards one circular polarization. According to an aspect of the present disclosure, the transmissivity of either left or right handedness of a predetermined wavelength or wavelength range through the electro-optic element 10 in the first state may be greater than about 10%, greater than about 12%, greater than about 25%, greater than about 50%, greater than about 55%, or greater than about 85%. For example, the electrochromic device 28 can transmit left circularly polarized and absorb right circularly polarized light when turned on or transmit right circularly polarized and absorb left circularly polarized light when turned on. Aspects of the present disclosure may exhibit greater dynamicrange, be more neutral in color, be more durable, and be less synthetically rigorous and less costly to incorporate in devices.

[0047] Turning to FIGS. 2A-2B, non-limiting examples of the anodic compound 22, including chemical compounds of phenazine derivatives, are illustrated. In some examples, the electrochromic medium 14 may include a combination of two or more anodic components which may include a single phenazine derivative or be a combination of two or more different phenazine derivatives. According to the present disclosure, at least one of the one or more R groups coupled with the anodic compound 22 (e.g., side chain modifications Ri, R2, R3, R4) provides chiral functional groups to the anodic compound 22. Therefore, the anodic compound 22 can exhibit dichroic behavior as an individual monomer and if / when the anodic compound 22 is further assembled into a polymer without the need to add a homochiral dopant molecule. In some aspects, chirality can be built into the anodic compound 22 without the inclusion of an additional R group.

[0048] Turning to FIGS. 3A-3C, non-limiting examples of the cathodic compound 18, including chemical compounds of viologen derivatives, are illustrated. The cathodic compound 18 of the electrochromic medium 14 can include one or more cathodic components, which can include a reducible compound. In some examples, the electrochromic medium 14 may include a single viologen derivative or be a combination of two or more different viologen derivatives. According to the present disclosure, at least one of the one or more R groups coupled with the cathodic compound 18 (e.g., side chain modifications Ri, R2, R3, R4) provides chiral functional groups to the cathodic compound 18. Therefore, the cathodic compound 18 can exhibit dichroic behavior as an individual monomer and if / when the cathodic compound 18 is further assembled into a polymer without the need to add a homochiral dopant molecule. In some aspects, chirality can be built into the cathodic compound 18 without the inclusion of an additional R group. For example, the cathodic compounds 18 illustrated in FIGS. 3B and 3C are chiral as illustrated.

[0049] Referring now to FIGS. 2A-3C, the R groups included within the cathodic compound 18 and the anodic compound 22 may be in the form of single enantiomer chiral units or monomers, which function to introduce chirality into the cathodic and anodic compounds 18,22 (e.g., homochiral functional group 26). Optionally, some of the R groups may be synthesized into the compounds 18, 22 to include formula enhancing properties. Formula enhancing properties may include increasing solubility of the formulation, or facilitating incorporation of cathodic or anodic compounds into a polymeric structure. Non-limiting examples of formula enhancing Ri and R2 R groups may include a methyl group; an alkyl carbon chain comprising of 2-11 carbon atoms terminated in a methyl group; an alkyl carbon chain comprising of 2-12 carbon atoms terminated in an hydroxyl, amine, thiol, ketone, vinyl, ethynyl, acrylic ester, isocyanate, epoxide, carboxylic acid, carboxylic ester, carboxylic anhydride, or acyl chloride, or combinations thereof. The R groups may include the same or different moieties. Non-limiting examples of formula enhancing R3 and R4 R groups may include hydrogen; carboxylic ester; an alkyl carbon chain comprising of 2-11 carbon atoms terminating in a methyl group; an alkyl carbon chain comprising of 2-12 carbon atoms terminating in a hydroxyl, amine, thiol, ketone, vinyl, ethynyl, acrylic ester, isocyanate, epoxide, carboxylic acid, carboxylic ester, carboxylic anhydride, or acyl chloride, or combinations thereof. Non-limiting examples of formula enhancing Rs, Re, and R7 R groups may include a methyl; carboxylic acid; carboxylic ester; ketone; an alkyl carbon chain comprising of 2-11 carbon atoms terminated in a methyl; an alkyl carbon chain comprising of 2-12 carbon atoms terminated in an hydroxyl, amine, thiol, ketone, vinyl, ethynyl, acrylic ester, isocyanate, epoxide, carboxylic acid, carboxylic ester, carboxylic anhydride, or acyl chloride; or combinations thereof. Non-limiting examples of the Ri, R2, R3, and R4 R groups which may be included to introduce chirality may include ((lS,2S)-cyclohexane-l,2-diyl)bis(methylene) (as shown in FIG. 4A) or ((lR,2R)-cyclohexane-l,2-diyl)bis(methylene), which is the enantiomer of the structure of FIG. 4A, (R)-l,l'-binaphthyl-2,2'-diyl (as shown in FIG. 4B) or (S)-l,l'- bi naphthy 1-2, 2' -diyl, which is the enantiomer of the structure of FIG. 4B, (R)-l, l'-binaphthy I- 2,2'-bis(alkoxy)-6,6'-diyl) (as shown in FIG. 4C) or (S)-l,l'-binaphthyl-2,2'-bis(alkoxy)-6,6'- diyl), which is the enantiomer of the structure of FIG. 4C, or any of the chemical compounds illustrated in FIGS. 4D-4G, which illustrate various chemical structures of exemplary homochiral chemical moieties that include generalized substituents according to the present disclosure. While the chemical compounds illustrated in FIGS. 4A-4G illustrate one particularenantiomer, the corresponding pure enantiomers of each structure are within the scope of aspects described herein. Again, the purpose of the selected functional R groups may be to increase solubility of the compound (e.g., 18, 22) in a particular solvent and / or to introduce chirality to the compound (e.g., 18, 22). Additionally, some of the R groups may be synthesized into the compounds 18, 22 to facilitate incorporation of cathodic or anodic compounds into a polymeric structure. Further, the selected functional R groups may enable the cathodic compound 18 and the anodic compound 22 to have ease of synthesis due to the number of synthetic steps involved, the yield of each synthetic step and / or the ease of purification after each synthetic step.

[0050] The cathodic compound 18 and the anodic compound 22 of the present disclosure may exhibit optimal and greater extinction ratios due to the close proximity of the homochiral functional group 26 to the molecular orbitals of the electrochromic moiety that is responsible for the visible wavelength transition dipole. In some examples, a distance from homochiral functional group 26 to, or away from, the corresponding molecular orbital of the electrochromic moiety may be in a range of approximately 1.5-4.5 Angstroms (A), approximately 1.0-5.0 A, approximately 0.75-10 A, and any and all values therebetween. Chemically tethering the homochiral functional group 26 directly to the electrochromic moiety ensures that changes in the temperature and redox state of the electrochromic medium 14 during device operation (e.g., electrochemical switching) that could lead to changes in the morphology of the medium 14 have minimal impact on the dichroic characteristics of the switchable absorption. Further, the cathodic compound 18 and the anodic compound 22 have been specifically tailored to include rigid molecular fragments that join the homochiral functional group 26 to the electrochromic moiety, resulting in a narrower range of available spatial configurations for the cathodic compound 18 and the anodic compound 22. Molecular features that impart rigidity help to limit variation in spatial separation between the homochiral functional group and the electrochromic moiety, as well as their orientation in space relative to one another. The rigid and / or shorter molecular fragments that join the functional group 26 to the electrochromic moiety may provide for a more efficient device operation.

[0051] In some aspects of the present disclosure, a plurality of cathodic and / or anodic species may be used in a same formulation each including different electrical potentials needed to reduce and oxidize the species respectively. For example, a specific electrical potential can be applied to the electro-optic element 10 that is specific to reduce or oxidize one of the either cathodic compound 18 or anodic compound 22 respectively. Accordingly, a higher electrical potential would be needed to reduce or oxidize the other of either the cathodic compound 18 or anodic compound 22, respectively. For an example with a plurality of cathodic and / or anodic species, at least one of the cathodic compound 18 and the anodic compound 22 can include at least two corresponding cathodic or anodic species that undergo changes in transmittance at different electrical reducing or oxidizing potentials.

[0052] As previously discussed, the electro-optic element 10 allows the electrochromic device 28 to be operable between the first state, a substantially clear state (e.g., a high transmission state, such as the inactivated state or off state) to the second state, a substantially dark or darkened state (e.g., a low transmission state, such as the activated or on state), as well as intermediate states thereto, in the event that one or more of the anodic and the cathodic components are oxidized (during the second state) and reduced (during the first state), respectively. As previously stated, different electrical potentials may be needed to reduce and oxidize a plurality of cathodic and / or anodic species; the plurality of cathodic and / or anodic species within the electro-optic element 10 may allow for a device with multiple intermediate states. Due to the presence of the homochiral functional groups 26, the electro-optic element 10, in the activated, or darkened state the electrochromic medium 14 can preferentially absorb a particular handedness of circularly polarized light, thereby providing circular dichroism. Accordingly, electro-optic elements 10 of the present disclosure can be in the form of "switchable" absorptive polarizers due to the ability of the electrochromic medium 14 providing switchable dichroic absorption in the visible light wavelength region. In other words, the electrochromic medium 14 can reversibly generate a dichroic absorbance in the visible wavelength region. In specific examples, the cathodic compound 18 and the anodic compound 22 may filter or absorb opposite circular polarizations of light in the visible spectrum. In other examples, the cathodic compound 18 and the anodic compound 22 mayfilter or absorb the same circular polarizations of light in the visible spectrum. In some aspects, the electrochromic medium 14 may include a mixture of different materials (e.g., anodic compounds 22 and cathodic compounds 18) that individually filter opposite circular polarizations when powered and undergo coloration at different biases. Such a device 28 may filter no polarized light, visible light of one polarization, or visible light of both polarizations.

[0053] In other implementations, alcohol moieties may be incorporated on monomeric forms of the cathodic compound 18 and / or the anodic compound 22 to form cross-linked polymer films on substrates. In other implementations, monomeric forms of the cathodic compound 18 and / or the anodic compound 22 may be incorporated as pendant groups onto a polymer before application to a substrate. In specific examples, the polymer may be an isotactic polymer. Additionally, the cathodic film 36 may contain a single enantiomer of a chiral moiety on the backbone of the polymeric chains, and / or as pendant groups, while the anodic film 40 may contain the single enantiomer of a chiral moiety on the backbone of the polymer chains, and / or as pendant groups. In another example, the cathodic film 36 may contain alcohol moieties incorporated on the backbone of the polymeric chains, and / or as the pendant groups of the polymeric chains to form cross-linked polymer films, while the anodic film 40 may contain alcohol moieties incorporated on the backbone of the polymeric chains, and / or as the pendant groups of the polymeric chains to form cross-linked polymer films. In yet another example, the cathodic film 36 may contain the single enantiomer of the chiral moiety as pendant groups onto an isotactic polymer, which may or may not separately include the alcohol moieties for chemical crosslinking. The anodic film 40 may contain the single enantiomer of the chiral moiety as pendant groups onto an isotactic polymer, which may or may not separately include the alcohol moieties for chemical crosslinking. Advantageously, implementations of the electrochromic medium 14 in film form can amplify the desired chiroptic effect as the effective local concentration of the homochiral functional group 26 may be higher. For example, when the homochiral functional group 26 exists free and / or in a solution, which may be an electrolyte solution, the homochiral functional group 26 may be characterized by Brownian motion and be allowed to randomly diffuse throughout thesolution. The effective local concentration would be higher with the electrochromic medium 14 in film form as the homochiral functional groups 26 would be directly tethered to the film.

[0054] Additionally, the electrochromic medium 14 can include additional components or layers, non-limiting examples of which include polarizers, anti-reflective layers, filters, resistive layers, ultraviolet light reflecting or absorbing layers, gas diffusion barrier layers, water vapor diffusion barrier layers, etc. In some examples, the electrochromic medium 14 may include homochiral, non-electroactive species (e.g., as components of the solvent and / or polymer gel electrolyte) that may enhance the variable dichroic absorption of the chiral electrochromic elements within the electrochromic medium 14. In further examples, the electrochromic medium 14, the cathodic film layer 36 and / or the anodic film layer 40 can include an ion conduction layer disposed thereon. The ion conduction layer can be configured to be conductive to positively or negatively charged ions, such as H+or Li+, but is low in electron conductivity in comparison, light absorbing, light stabilizing, thermal stabilizing, antioxidants, oxygen scavengers, thickeners, viscosity modifiers, tint / color providing agents, UV stabilizers, redox buffers, and the like.

[0055] The homochiral functional groups in close proximity to the corresponding optical transition dipole according to aspects of the present disclosure provide a variety of benefits, especially when used in electrochromic devices. The compounds of the present disclosure exhibit high extinction ratios due to the homochiral moieties being tethered in a short and / or rigid manner to the molecular orbitals of the electrochromic moiety responsible for the visible wavelength transition dipole. The short and / or rigid connections of the homochiral moieties to the electrochromic moiety also may result in a narrower range of available spatial configurations which may increase the extinction ratio. The homochiral functional groups in close proximity to the corresponding transition dipole may allow for faster and / or more efficient activation of absorption of circularly polarized light in the visible spectrum. The compounds in the present disclosure may be easily synthesized due to the small number of synthetic steps involved, the yield of each synthetic step, and / or the ease of purification after each synthetic step. The electrochromic devices as described in the present disclosure provide cathodic and anodic species that are configured to absorb circularly polarized light in thevisible spectrum. In some aspects of the present disclosure, a plurality of cathodic and / or anodic species may be used in a same formulation each includes different electrical potentials needed to reduce and oxidize the species respectively. The different electrical potentials needed to reduce and oxidize may allow for multiple states of non-absorbance, absorbance of one-handedness of circularly polarized light, and / or a darken state with more absorbance of visible light.

[0056] According to one aspect of the present disclosure, a medium for electro-optic element includes a cathodic compound and an anodic compound, wherein at least one of the cathodic compound and the anodic compound include a homochiral functional group in close proximity to a corresponding optical transition dipole of the one of the cathodic compound and the anodic compound, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

[0057] According to another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound exhibit circular dichroic behavior in the visible spectrum when reduced or oxidized, respectively.

[0058] According to yet another aspect of the present disclosure, the medium is in a form of an electrolyte solvent.

[0059] According to another aspect of the present disclosure, the medium is in a form of a polymer.

[0060] According to yet another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound is a pendant group bonded to the polymer.

[0061] According to another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound may be a monomer on a polymer chain.

[0062] According to yet another aspect of the present disclosure, the polymer may be an isotactic polymer.

[0063] According to another aspect of the present disclosure, each of the cathodic compound and the anodic compound include a homochiral functional group.

[0064] According to yet another aspect of the present disclosure, the cathodic compound and the anodic compound filter opposite circular polarizations of light in the visible spectrum.

[0065] According to another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound include a plurality of corresponding cathodic or anodic species to generate different electrical potentials needed to reduce and oxidize the species.

[0066] According to yet another aspect of the present disclosure, a device may include the electro-optic medium.

[0067] According to another aspect of the present disclosure, a cathodic medium for an electro-optic element, may include a chemical compound of Formula (I) or (II) or (III):orwherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

[0068] According to yet another aspect of the present disclosure, an anodic medium for an electro-optic element, includes a chemical compound of Formula (IV) or (V):wherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

[0069] According to one aspect of the present disclosure, a medium for electro-optic element includes a cathodic compound and an anodic compound, wherein the cathodic compound and the anodic compound are dissolved into an electrolyte solvent, the electrolyte solvent including a homochiral functional group, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

[0070] According to another aspect of the present disclosure, a medium for an electro-optic element includes a cathodic compound and an anodic compound, wherein at least one of the cathodic compound and the anodic compound include a homochiral functional group 1.5-10 A away from a corresponding optical transition dipole of the one of the cathodic compound and the anodic compound, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

[0071] According to yet another aspect of the present disclosure, the cathodic compound is a chemical compound of Formula (I) or (II) or (III):orwherein at least one of Ri, R2, R3 and R4 includes a single enantiomer chiral unit.

[0072] According to another aspect of the present disclosure, the anodic compound is a chemical compound of Formula (IV) or (V):wherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

[0073] According to yet another aspect of the present disclosure, at least one of Ri, R2, R3 and R4 includes ((lS,2S)-cyclohexane-l,2-diyl)bis(methylene), ((lR,2R)-cyclohexane-l,2- diyl)bis(methylene), (R)-l,l'-binaphthyl-2,2'-diyl, (S)-l,l'-binaphthyl-2,2'-diyl, (R)-l,l'- binaphthyl-2,2'-bis(alkoxy)-6,6'-diyl), or (S)-l,l'-binaphthyl-2,2'-bis(alkoxy)-6,6'-diyl).

[0074] According to another aspect of the present disclosure, at least one of Ri, R2, R3 and R4 includes a structure of the Formula (VI), (VII), (VIII) or (IX):(IX).

[0075] According to yet another aspect of the present disclosure, at least one of Rs, Re, and R? include a methyl; carboxylic acid; carboxylic ester; ketone; an alkyl carbon chain including 2-11 carbon atoms terminated in a methyl; an alkyl carbon chain including 2-12 carbon atoms terminated in an hydroxyl, amine, thiol, ketone, vinyl, ethynyl, acrylic ester, isocyanate, epoxide, carboxylic acid, carboxylic ester, carboxylic anhydride, or acyl chloride; or combinations thereof.

[0076] According to another another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound exhibit circular dichroic behavior in the visible spectrum when reduced or oxidized, respectively.

[0077] According to yet another aspect of the present disclosure, the medium is in a form of a polymer.

[0078] According to another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound is a pendant group bonded to the polymer.

[0079] According to yet another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound is a monomer on a polymer chain.

[0080] According to another aspect of the present disclosure, the polymer is an isotactic polymer.

[0081] According to yet another aspect of the present disclosure, each of the cathodic compound and the anodic compound include a homochiral functional group.

[0082] According to another aspect of the present disclosure, the cathodic compound and the anodic compound filter opposite circular polarizations of light in the visible spectrum.

[0083] According to yet another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound include a plurality of corresponding cathodicor anodic species that generate different electrical potentials to reduce and oxidize the species.

[0084] According to another aspect of the present disclosure, the cathodic compound and the anodic compound filter opposite circular polarizations of light in the visible spectrum.

[0085] According to one aspect of the present disclosure, a medium for an electro-optic element, includes a cathodic compound and an anodic compound, wherein at least one of the cathodic compound and the anodic compound include a homochiral functional group 1.5-10 A away from a corresponding optical transition dipole of the one of the cathodic compound and the anodic compound, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

[0086] According to another aspect of the present disclosure, the homochiral functional group is 1.5-4.5 A away from the corresponding optical transition dipole of the one of the cathodic compound and the anodic compound.

[0087] According to yet another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound exhibit circular dichroic behavior in the visible spectrum when reduced or oxidized, respectively.

[0088] According to yet another aspect of the present disclosure, the medium is in a form of an electrolyte solvent.

[0089] According to yet another aspect of the present disclosure, the medium is in a form of a polymer.

[0090] According to yet another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound is a pendant group bonded to the polymer.

[0091] According to yet another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound is a monomer on a polymer chain.

[0092] According to yet another aspect of the present disclosure, the polymer is an isotactic polymer.

[0093] According to yet another aspect of the present disclosure, each of the cathodic compound and the anodic compound include a homochiral functional group.T1

[0094] According to one aspect of the present disclosure, the cathodic compound and the anodic compound filter opposite circular polarizations of light in the visible spectrum.

[0095] According to another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound include a plurality of corresponding cathodic or anodic species that undergo changes in transmittance at different electrical reducing or oxidizing potentials.

[0096] According to one another aspect of the present disclosure, a cathodic medium for an electro-optic element includes a chemical compound of Formula (I) or (II) or (III):ororwherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

[0097] According to another aspect of the present disclosure, at least one of Ri, R2, R3 and R4 includes ((lS,2S)-cyclohexane-l,2-diyl)bis(methylene), ((lR,2R)-cyclohexane-l,2-diyl)bis(methylene), (R)-l,l'-binaphthyl-2,2'-diyl, (S)-l,l'-binaphthyl-2,2'-diyl, (R)-l,l'- binaphthyl-2,2'-bis(alkoxy)-6,6'-diyl), or (S)-l,l'-binaphthyl-2,2'-bis(alkoxy)-6,6'-diyl).

[0098] According to yet another aspect of the present disclosure, at least one of Ri, R2, R3 andR4 includes a structure of the Formula (VI), (VII), (VIII) or (IX):(VIII) or

[0099] According to yet another aspect of the present disclosure, at least one of Rs, Re, and R? include a methyl; carboxylic acid; carboxylic ester; ketone; an alkyl carbon chain including 2-11 carbon atoms terminated in a methyl; an alkyl carbon chain including 2-12 carbon atoms terminated in an hydroxyl, amine, thiol, ketone, vinyl, ethynyl, acrylic ester, isocyanate, epoxide, carboxylic acid, carboxylic ester, carboxylic anhydride, or acyl chloride; or combinations thereof.

[0100] According to another aspect of the present disclosure, the medium is configured to reversibly generate a dichroic absorbance.

[0101] According to another aspect of the present disclosure, an anodic medium for an electro-optic element includes a chemical compound of Formula (IV) or (V):wherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

[0102] According to yet another aspect of the present disclosure, at least one of Ri, R2, R3 and R4 includes ((lS,2S)-cyclohexane-l,2-diyl)bis(methylene), ((lR,2R)-cyclohexane-l,2- diyl)bis(methylene), (R)-l,l'-binaphthyl-2,2'-diyl, (S)-l,l'-binaphthyl-2,2'-diyl, (R)-l,l'- binaphthyl-2,2'-bis(alkoxy)-6,6'-diyl), or (S)-l,l'-binaphthyl-2,2'-bis(alkoxy)-6,6'-diyl).

[0103] According to yet another aspect of the present disclosure, at least one of Ri, R2, R3 and R4 includes a structure of the Formula (VI), (VII), (VIII) or (IX):(VIII) or

[0104] According to one aspect of the present disclosure, at least one of Rs, Re, and R? include a methyl; carboxylic acid; carboxylic ester; ketone; an alkyl carbon chain including 2-11 carbon atoms terminated in a methyl; an alkyl carbon chain including 2-12 carbon atoms terminated in an hydroxyl, amine, thiol, ketone, vinyl, ethynyl, acrylic ester, isocyanate, epoxide, carboxylic acid, carboxylic ester, carboxylic anhydride, or acyl chloride; or combinations thereof.

[0105] According to another aspect of the present disclosure, the medium is configured to reversibly generate a dichroic absorbance.

[0106] According to one another aspect of the present disclosure, a medium for an electrooptic element includes a cathodic compound and an anodic compound, wherein the cathodic compound and the anodic compound are dissolved into an electrolyte solvent, the electrolyte solvent including a homochiral functional group, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

[0107] According to yet another aspect of the present disclosure, the at least one of the cathodic compound and the anodic compound exhibit circular dichroic behavior in the visible spectrum when reduced or oxidized, respectively.

[0108] According to yet another aspect of the present disclosure, the cathodic compound and the anodic compound filter opposite circular polarizations of light in the visible spectrum.

[0109] It will be understood by one having ordinary skill in the art that construction of the described disclosure and other components is not limited to any specific material. Other exemplary embodiments of the disclosure disclosed herein may be formed from a wide variety of materials, unless described otherwise herein.

[0110] For purposes of this disclosure, the term "coupled" (in all of its forms, couple, coupling, coupled, etc.) generally means the joining of two components (chemical, electrical or mechanical) directly or indirectly to one another. Such joining may be stationary in nature or movable in nature. Such joining may be achieved with the two components (chemical, electrical or mechanical) and any additional intermediate members being integrally formed as a single unitary body with one another or with the two components. Such joining may be permanent in nature or may be removable or releasable in nature unless otherwise stated.

[0111] It is also important to note that the construction and arrangement of the elements of the disclosure, as shown in the exemplary embodiments, is illustrative only. Although only a few embodiments of the present innovations have been described in detail in this disclosure, those skilled in the art who review this disclosure will readily appreciate that many modifications are possible (e.g., variations in sizes, dimensions, structures, shapes and proportions of the various elements, values of parameters, mounting arrangements, use of materials, colors, orientations, etc.) without materially departing from the novel teachings and advantages of the subject matter recited. For example, elements shown as integrally formed may be constructed of multiple parts, or elements shown as multiple parts may be integrally formed, the operation of the interfaces may be reversed or otherwise varied, the length or width of the structures and / or members or connector or other elements of the system may be varied, the nature or number of adjustment positions provided between the elements may be varied. It should be noted that the elements and / or assemblies of the system may be constructed from any of a wide variety of materials that provide sufficient strength or durability, in any of a wide variety of colors, textures, and combinations. Accordingly, all such modifications are intended to be included within the scope of the present innovations. Other substitutions, modifications, changes, and omissions may be made in the design, operating conditions, and arrangement of the desired and other exemplary embodiments without departing from the spirit of the present innovations.

[0112] It will be understood that any described processes or steps within described processes may be combined with other disclosed processes or steps to form structures withinthe scope of the present disclosure. The exemplary structures and processes disclosed herein are for illustrative purposes and are not to be construed as limiting.

[0113] It is also to be understood that variations and modifications can be made on the aforementioned structures and methods without departing from the concepts of the present disclosure, and further it is to be understood that such concepts are intended to be covered by the following claims unless these claims by their language expressly state otherwise.

Claims

CLAIMSWhat is claimed is:

1. A medium for an electro-optic element, comprising: a cathodic compound; and an anodic compound, wherein at least one of the cathodic compound and the anodic compound comprise a homochiral functional group 1.5-10 A away from a corresponding optical transition dipole of the one of the cathodic compound and the anodic compound, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

2. The medium for an electro-optic element of claim 1, wherein the homochiral functional group is 1.5-4.5 A away from the corresponding optical transition dipole of the one of the cathodic compound and the anodic compound.

3. The medium for an electro-optic element of either one of claims 1 or 2, wherein the at least one of the cathodic compound and the anodic compound exhibit circular dichroic behavior in the visible spectrum when reduced or oxidized, respectively.

4. The medium for an electro-optic element of any one of claims 1-3, wherein the medium is in a form of an electrolyte solvent.

5. The medium for an electro-optic element of any one of claims 1-3, wherein the medium is in a form of a polymer.

6. The medium for an electro-optic element of claim 5, wherein the at least one of the cathodic compound and the anodic compound is a pendant group bonded to the polymer.

7. The medium for an electro-optic element of claim 5, wherein the at least one of the cathodic compound and the anodic compound is a monomer on a polymer chain.

8. The medium for an electro-optic element of claim 6, wherein the polymer is an isotactic polymer.

9. The medium for an electro-optic element of any one of claims 1-6, wherein each of the cathodic compound and the anodic compound comprise a homochiral functional group.

10. The medium for an electro-optic element of claim 9, wherein the cathodic compound and the anodic compound filter opposite circular polarizations of light in the visible spectrum.

11. The medium for an electro-optic element of claim 1, wherein the at least one of the cathodic compound and the anodic compound comprise a plurality of corresponding cathodic or anodic species that undergo changes in transmittance at different electrical reducing or oxidizing potentials.

12. A device including the electro-optic medium of any one of claims 1-11.

13. A cathodic medium for an electro-optic element, comprising: a chemical compound of Formula (I) or (II) or (III):orwherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

14. The cathodic medium for an electro-optic element of claim 13, wherein at least one of Ri, R2, R3 and R4 comprises ((lS,2S)-cyclohexane-l,2-diyl)bis(methylene), ((1R,2R)- cyclohexane-l,2-diyl)bis(methylene), (R)-l,l'-binaphthyl-2,2'-diyl, (S)-l,l'-binaphthyl-2,2'- diyl, (R)-l,l'-binaphthyl-2,2'-bis(alkoxy)-6,6'-diyl), or (S)-l, -binaphthyl-2,2'-bis(alkoxy)-6,6'- diyl).

15. The cathodic medium for an electro-optic element of claim 13, wherein at least one of Ri, R2, R3 and R4 comprises a structure of the Formula (VI), (VII), (VIII) or (IX):or16. The cathodic medium for an electro-optic element of claim 15, wherein at least one of Rs, Re, and R? comprise a methyl; carboxylic acid; carboxylic ester; ketone; an alkyl carbon chain comprising of 2-11 carbon atoms terminated in a methyl; an alkyl carbon chain comprising of 2-12 carbon atoms terminated in an hydroxyl, amine, thiol, ketone, vinyl, ethynyl, acrylic ester, isocyanate, epoxide, carboxylic acid, carboxylic ester, carboxylic anhydride, or acyl chloride; or combinations thereof.

17. The cathodic medium for an electro-optic element of any one of the claims 13-16, wherein the medium is configured to reversibly generate a dichroic absorbance.

18. An anodic medium for an electro-optic element, comprising: a chemical compound of Formula (IV) or (V):wherein at least one of Ri, R2, R3 and R4 include a single enantiomer chiral unit.

19. The anodic medium for an electro-optic element of claim 18, wherein at least one of Ri, R2, R3 and R4 comprises ((lS,2S)-cyclohexane-l,2-diyl)bis(methylene), ((1R,2R)- cyclohexane-l,2-diyl)bis(methylene), (R)-l,l'-binaphthyl-2,2'-diyl, (S)-l,l'-binaphthyl-2,2'- diyl, (R)-l,l'-binaphthyl-2,2'-bis(alkoxy)-6,6'-diyl), or (S)-l, -binaphthyl-2,2'-bis(alkoxy)-6,6'- diyl).

20. The anodic medium for an electro-optic element of claim 18, wherein at least one ofRi, R2, R3 and R4 comprises a structure of the Formula (VI), (VII), (VIII) or (IX):

21. The anodic medium for an electro-optic element of claim 18, wherein at least one of Rs, Re, and R? comprise a methyl; carboxylic acid; carboxylic ester; ketone; an alkyl carbon chain comprising of 2-11 carbon atoms terminated in a methyl; an alkyl carbon chain comprising of 2-12 carbon atoms terminated in an hydroxyl, amine, thiol, ketone, vinyl, ethynyl, acrylic ester, isocyanate, epoxide, carboxylic acid, carboxylic ester, carboxylic anhydride, or acyl chloride; or combinations thereof.

22. The anodic medium for an electro-optic element of any one of the claims 18-21-, wherein the medium is configured to reversibly generate a dichroic absorbance.

23. A medium for an electro-optic element, comprising: a cathodic compound; and an anodic compound, wherein the cathodic compound and the anodic compound are dissolved into an electrolyte solvent, the electrolyte solvent comprising a homochiral functional group, thereby configuring the medium to reversibly generate a dichroic absorbance in the visible spectrum.

24. The medium for an electro-optic element of claim 23, wherein the at least one of the cathodic compound and the anodic compound exhibit circular dichroic behavior in the visible spectrum when reduced or oxidized, respectively.

25. The medium for an electro-optic element of either one of claims 21 or 24, wherein the cathodic compound and the anodic compound filter opposite circular polarizations of light in the visible spectrum.

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