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Terpyridyl-fluorene metal hybrid polymer and electrochromic device containing same

An electrochromic device, terpyridine technology, which is applied in the fields of instrumentation, organic chemistry, optics, etc., can solve the problems of poor dissolution processing performance, difficult to make electrochromic films, etc., achieve good thermal stability, improve solubility, promote The effect of electron cloud delocalization

Inactive Publication Date: 2014-02-05
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of material has strong rigidity, poor dissolution processability, and it is difficult to produce large-area electrochromic films due to electrochemical polymerization.

Method used

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  • Terpyridyl-fluorene metal hybrid polymer and electrochromic device containing same
  • Terpyridyl-fluorene metal hybrid polymer and electrochromic device containing same
  • Terpyridyl-fluorene metal hybrid polymer and electrochromic device containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 Ligand (7-bis(phenyl-4'-(2,2':6',2"-terpyridine)-9,9-bis(2-ethylhexyl)fluorene ( L1 )Synthesis:

[0036] The synthetic route is as follows:

[0037]

[0038]

[0039] (1) 9,9-bis(2-ethylhexyl)fluorene (compound 2 ) synthesis: Dissolve fluorene (compound 1) (8.48g, 51.1mmol) in anhydrous THF (120ml), stir, and vacuumize the solution and then pass it into N 2 After many times, the solution was cooled to -78°C, and 42.92 ml n-BuLi (107.31 mmol, 2.5M) was slowly added dropwise to the solution. A THF (25ml) solution of 2-ethylhexane (g, 117.53mmol) was slowly added dropwise to the reaction system, the reaction solution was slowly raised to room temperature, and stirred for 3h. Pour the mixture into water, extract with ethyl acetate several times, combine the organic phases, wash the organic phases with saturated brine, separate the liquids, and wash the organic phases with anhydrous NaSO 4 After drying and concentrating, it is separated and purified b...

Embodiment 2

[0047] Example 2 Ligand 7-bis(phenyl-4'-(2,2':6',2"-terpyridine)-9,9-two-dodecylfluorene ( L2 )Synthesis:

[0048] Ligand in synthetic method and embodiment 1 The synthesis method is the same, only need to change the 1-bromo-2-ethylhexane in the step (1) of Example 1 to n-dodecyl bromide. The resulting product is the ligand 2， Expressed as L2, the yield is 71.8%, the melting point is 67°C, and its molecular formula is as follows:

[0049]

[0050] UV absorption peak position: λ ab =350 nm (ε=6′10 4 cm -1 × M -1 , CH 2 Cl 2 solvent); 1 H NMR (400 MHz, CDCl 3 , TMS): δ 0.80, 0.82, 0.83 (t, 6H, -CH 3 ), 1.10, 1.19, 1.24 (t, 40 H, -CH 2 -), 2.09, 2.11, 2.13 (t, 4H, -CH 2-), 7.36, 7.38, 7.39 (t, 4H, pyr-H), 7.66, 7.68, 7.70 (t, 4H, Ar-H), 7.83, 7.85 (d, 6H, fluorene-H), 7.88, 7.90, 7.92 (t, 4H, Ar-H), 8.04, 8.06 (d, 4H, pyr-H), 8.69, 8.71 (d, 4H, pyr-H), 8.76, 8.77 (d, 4H, pyr-H) , 8.83 (s, 4H, pyr-H).

Embodiment 3

[0051] Example three terpyridine-fluorene iron hybrid polymer ([L1-Fe] m ) preparation:

[0052] At room temperature, add L1 (0.0475 g, 0.05 mmol) and Fe 2 SO 4 Fe 2 SO 4 Ammonium hexafluorophosphate with 10 times the amount of substance, continue to stir for 0.5h, filter with suction, wash with absolute ethanol and absolute ethanol / acetonitrile, and dry in a vacuum oven to obtain the product [L1-Fe] m . Yield: 85%. The melting point is greater than 400°C, and the critical decomposition temperature is 332°C. Structural Characterization Data: 1 H NMR (400 MHz, DMSO, TMS): δ 0.593 (s, 12H, -CH 3 ), 0.858 (s, 18H, alkyl hydrogen), 2.232 (s, 4H, -CH 2 -),7.242 (s, 8H, Ar-H),7.577 (s, 4H, Ar-H),8.087(s, 6H, fluorene-H), 8.246(s, 4H, pyr-H),8.721, 8.738 (s, 4H, pyr-H), 8.810, 8.824(s, 4H, pyr-H), 9.147 (s, 4H, pyr-H), 9.794(s, 4H, pyr-H).

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Abstract

The invention belongs to field of an electrochromic material, and particularly relates to a terpyridyl-fluorene metal hybrid polymer and an electrochromic device containing the same. The solubility of a rigid conjugate structure of a main chain can be improved by a flexible side chain group of the terpyridyl-fluorene metal hybrid polymer prepared by the invention, so that the terpyridyl-fluorene metal hybrid polymer has good solubility in common solvents such as chlorobenzene, dimethyl formamide (DMF) and the like, and can be easily processed to form a film by a solution method; meanwhile, the terpyridyl-fluorene metal hybrid polymer has the characteristics of an inorganic material, namely high heat stability by the rigid main chain structure and organic and inorganic metal complexes; terpyridyl and fluorenyl are in conjugated connection by metal ion coordination, so that electron cloud delocalization is facilitated, and the photoelectric response sensitivity is improved; the all-solid state electrochromic device prepared from the terpyridyl-fluorene metal hybrid polymer is significant in color change, and obvious in aberration, and has important application value in the field of organic electrochromism.

Description

technical field [0001] The invention belongs to the field of electrochromic materials, in particular to a terpyridine-fluorene metal hybrid polymer and an electrochromic device comprising the polymer. Background technique [0002] Electrochromic materials (electrochromic, EC) refer to a class of intelligent materials that undergo stable and reversible redox reactions under the action of an electric field, and exhibit reversible changes in color (or transparency) in appearance. Electrochromic Devices (ECD) can be used in display panels, anti-glare rearview mirrors, and intelligent color-changing windows; in addition, as a smart material, they are also used in military camouflage (such as military color-changing clothing / stealth equipment). have potential application value. [0003] Electrochromic materials include inorganic electrochromic and organic electrochromic materials. Organic electrochromic materials include organic dyes, conductive polymers and metal complexes; ino...

Claims

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Application Information

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IPC IPC(8): C08G79/00C07D213/22G02F1/15
Inventor 王筱梅张卫叶常青岳富民陈志刚李建康周宇扬梁作芹孙彬
Owner SUZHOU UNIV OF SCI & TECH
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