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Photosensitive dopant, preparation method thereof, self-assembly system and photoresponse device

A dopant and self-assembly technology, applied in the field of light regulation, can solve the problems of inapplicability, high synthesis cost, and small molecular size of photosensitizers, and achieve the effects of high ultraviolet absorption capacity, high molecular deformation index, and simple synthesis method.

Active Publication Date: 2017-04-19
SOUTH CHINA NORMAL UNIVERSITY +2
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Problems solved by technology

[0005] However, compared with chiral molecules, liquid crystal molecules and liquid crystal polymers, the molecular size of photosensitizers is too small, and the rearrangement effect of molecular self-assembly systems (including chiral molecules and liquid crystal molecules) driven by their conformation is limited.
Like the reported chiral photosensitive dopants of diarylethene derivatives, an excitation light of about 254nm is required to photoisomerize the diarylethene group, the adjustment efficiency is poor, and the irradiation time is long. Moreover, its synthesis cost is also high
In addition, it is also reported that spirooxazine derivatives are used as chiral photosensitive dopants, but even under unexcited conditions, the excited state molecules will quickly return to the ground state in about 20 seconds, indicating that the excited state The stability is very poor, so it cannot be applied under normal conditions

Method used

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  • Photosensitive dopant, preparation method thereof, self-assembly system and photoresponse device
  • Photosensitive dopant, preparation method thereof, self-assembly system and photoresponse device
  • Photosensitive dopant, preparation method thereof, self-assembly system and photoresponse device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] refer to figure 1 The synthetic route map of carrying out the synthesis of photoactive dopant:

[0037] (1) Add 10g of 3,5-di-aminobenzoic acid and 100mL of methanol into a single-necked flask, start stirring, slowly drop 5mL of concentrated sulfuric acid, and then reflux for 20-30 hours. After stopping the reaction, most of the solvent was evaporated by rotary evaporation, and then an appropriate amount of ethyl acetate and saturated sodium bicarbonate solution was added to make the pH of the system between 7-9, and the organic phase was obtained by liquid separation, and dried over sodium sulfate. Rotary evaporation gave methyl 3,5-di-aminobenzoate.

[0038] (2) Place 1 g of methyl 3,5-di-aminobenzoate in a beaker under ice-bath conditions, add 30 mL of water and 3.7 mL of concentrated hydrochloric acid; and prepare 5 mL of 0.824 g of sodium nitrite aqueous solution. Slowly drop the solution containing sodium nitrite into the beaker and react for 30 minutes.

[003...

Embodiment 2

[0044] refer to Figure 5 The synthetic route map of carrying out the synthesis of photoactive dopant:

[0045] Carry out the steps (1)-(5) identical with embodiment 1;

[0046] (6) Weigh 2g of R-binaphthol, 1.5g of potassium carbonate and 0.1g of potassium iodide in a single-necked flask, add 30mL of acetone to dissolve, start stirring and slowly add 0.751mL of n-bromobutane solution, and reflux for 2 days. Rotary evaporate the organic phase, add 100mL ethyl acetate and 3×100mL aqueous liquid extraction treatment, separate the organic phase, treat with anhydrous sodium sulfate, rotary evaporation, and column chromatography to obtain 2-n-butoxy (R) binaphthol. H NMR (400MHz d6-DMSO):δ=0.690(t,3H),δ=1.01(d,2H),δ=1.36(d,2H),δ=3.99(d,2H),δ=6.88(s ,1H),δ=7.02(s,1H),δ=7.14(s,1H),δ=7.22(d,2H), δ=7.33(d,2H),δ=7.55(s,1H),δ =7.84(d,2H),δ=7.91(s,1H),δ=8.00(s,1H),δ=9.25(s,1H).

[0047] (7) Weigh 0.69g of 3,5-bis-(4-butyl ether phenylazo)benzoic acid and 0.5g of 2-n-butoxy (R) binapht...

Embodiment 3

[0049] refer to Image 6 The synthetic route map of carrying out the synthesis of chiral photosensitive dopant:

[0050] Carry out the steps (1)-(5) identical with embodiment 1;

[0051] (6) Weigh 1g of R-binaphthol, 0.73g of potassium carbonate and 0.045g of potassium iodide into a single-necked flask, add 30mL of acetone to dissolve, start stirring and slowly add 0.45mL of n-bromohexane solution, and reflux for 2 days. Rotary evaporate the organic phase, add 100mL ethyl acetate and 3×100mL aqueous liquid extraction treatment, separate the organic phase, treat with anhydrous sodium sulfate, rotary evaporation, and column chromatography to obtain 2-n-butoxy (R) binaphthol. H NMR (400MHz d6-DMSO):δ=0.70(t,3H),δ=0.85-1.02(m,6H),δ=1.33(d,2H),δ=3.99(d,2H),δ=6.86 (s,1H),δ=7.02(s,1H),δ=7.12-7.33(m,5H),δ=7.55(s,1H),δ=7.91-8.01(m,4H),δ=9.25( s, 1H).

[0052] (7) Weigh 0.50g of 3,5-bis-(4-butyl ether phenylazo) benzoic acid and 0.325g of 2-n-hexyloxy (R) binaphthol, dissolve 25mL o...

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Abstract

The invention discloses a photosensitive dopant, a preparation method thereof, a self-assembly system and a photoresponse device. The chemical structure of molecules of the photosensitive dopant is characterized in that 3,5-bi-(4-hydroxyphenylazo) benzoic acid is adopted as a base framework, a carboxyl terminal is connected with a chirality group, and a hydroxyl terminal is connected with a flexible chain. Under stimulation of external light, a photosensitive group- di-azobenzene with high ultraviolet absorption capability can achieve quick response and can be isomerized, quick isomerization of the chirality group in the structure and even the entire molecules is further induced, and the deformation index of the molecules is higher and quicker. In the self-assembly system of the molecules, rearrangement of the molecules in the system can be triggered more obviously, and physicochemical characteristics, like optimal and electrical characteristics, of the system are regulated.

Description

technical field [0001] The invention relates to the technical field of light regulation, in particular to a photosensitive dopant, a preparation method thereof, a self-assembly system and a photoresponsive device. Background technique [0002] Stimuli-responsive materials convert physical and chemical signals such as light, electricity, heat and mechanics into other physical, chemical and biological signals, or convert physical, chemical and biological signals into other light by regulating the transport and arrangement of ions and molecules. , electricity, heat and mechanics and other physical and chemical signals, so as to spontaneously adapt to the surrounding environment. Such materials are playing an increasingly important role in many intelligent systems and devices such as drug loading, diagnosis, biological tissue engineering, intelligent optical systems, biosensing, microelectronic systems, dyes, textiles, and even energy and construction. [0003] Among them, phot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/58G02F1/13
CPCC09K19/586G02F1/1313
Inventor 李皓廖经纶李楠周国富
Owner SOUTH CHINA NORMAL UNIVERSITY
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