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Photochromic and electrochromic bifunctional compound and preparation method thereof

An electrochromic and photochromic technology, applied in chemical instruments and methods, organic chemistry, color-changing fluorescent materials, etc., can solve the problem of high cost, inability to increase molecular switching states, and the lack of relative properties of photochromic and electrochromic properties. Independence and other issues to achieve the effect of capacity increase

Inactive Publication Date: 2015-03-11
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dithienyl cyclopentene compound (Peters A, Branda N R, Journal of the American Chemical Society, 2003, 125, 3404) substituted by thiophene at the 2 and 2' positions can be photo-induced or electrically induced to open the ring, and is a A single-group bifunctional material, but the ring-opening body of this compound can only be induced by 365nm light to close the ring, so its photochromic and electrochromic properties are not relatively independent, and it cannot increase the switching state of the molecule
However, the synthesis route of bridging N-picoline salt or metal complex on the diarylethene unit is complicated and the cost is high
[0005] Triphenylamine polymer (Hsiao S H, Liou G S, Kung Y C, et al, Journal of Polymer Science: Part A: Polymer Chemistry, 2010, 48, 2798, Kung Y C, Liou G S, Hsiao S H, Journal of Polymer Science: Part A : Polymer Chemistry, 2009, 47, 1740, Hsiao S H, Liou G S, Wang H M, Journal of Polymer Science: Part A: Polymer Chemistry, 2009, 47, 2330) is one of the research hotspots of electrochromic materials, which have color Rich, good fatigue resistance, etc., but the solubility of the polymer is poor, and the modification of the group is difficult

Method used

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  • Photochromic and electrochromic bifunctional compound and preparation method thereof
  • Photochromic and electrochromic bifunctional compound and preparation method thereof
  • Photochromic and electrochromic bifunctional compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～3

[0036] Examples 1-3 are 1,2-bis(3-(2,5-dimethylthienyl))-4-(4-(N,N-dianilinophenyl))cyclopentene (3) Synthesis

Embodiment 1

[0037] Example 1: Synthesis of 1-(3-(2,5-dimethylthienyl))-3-(4-(N,N-diphenylaminophenyl))propenone (1)

[0038] Add 3-acetyl-2,5-dimethylthiophene (1.54g, 10mmol), 4-(N,N-diphenylamino)benzaldehyde (10mmol) into ethanol (140mL), stir, and add 15mL 13M sodium hydroxide solution was reacted at room temperature for 48 hours, suction filtered, washed with water, and recrystallized with ethanol to obtain 3.63 g of compound (1) (yellow powder, yield 92%). m.p.143.0~144.5℃; MS(APCI):m / z calcd for C 27 h 23 NOS:410.16[M+H] + ;found: 410.35; 1 H NMR (400MHz, CDCl 3 )δ: (ppm) 7.67 (d, J = 15.6Hz, 1H), 7.48 (d, J = 8.5Hz, 2H), 7.32 (t, J = 7.7Hz, 4H), 7.22 ~ 7.09 (m, 7H) ,7.08~6.99(m,3H),2.72(s,3H),2.46(s,3H); 13 C NMR (100MHz, CDCl 3 )δ: (ppm) 186.6, 150.0, 146.9, 146.4, 143.4, 137.1, 135.2, 129.5, 129.5, 128.1, 126.0, 125.4, 124.0, 122.6, 121.8, 15.8, 15.0.

Embodiment 2

[0039] Example 2: 1,5-bis(3-(2,5-dimethylthienyl))-3-(4-(N,N-dianilinophenyl))-1,5-pentanedione (2) Synthesis

[0040] N 2 Under protection, add 3-acetyl-2,5-dimethylthiophene (5.5mmol) and 20mL dry tetrahydrofuran (THF) to a 50mL four-necked flask, cool down to -25°C, and dropwise add lithium diisopropylamide (3mL, 2M), complete, react at this temperature for 30min, dropwise add 15mL of THF solution of the corresponding compound (1) (5mmol), complete, keep warm for 30min, naturally rise to room temperature for 2h, add water to quench the reaction, and Adjust the pH to 5-6 with 1N hydrochloric acid, extract with dichloromethane, wash with water, dry over sodium sulfate, spin dry, and separate by column chromatography to obtain 1.88 g of a yellow solid with a yield of 67%. m.p.44-45℃. 1 H NMR (400MHz, CDCl 3 )δ: (ppm) 7.21 (t, J = 7.7Hz, 4H), 7.09 (d, J = 8.3Hz, 2H), 7.06-6.93 (m, 10H), 3.88 (p, J = 6.9Hz, 1H) ,3.15(ddd,J=42.2,16.1,7.0Hz,4H),2.58(s,6H),2.39(s,6H); 13 C NM...

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Abstract

The invention discloses a photochromic and electrochromic bifunctional compound and a preparation method thereof. A triphenylamine group is introduced into a photochromic diarylethene compound. So the synthesized compound contains a triphenylamine group and a photochromic diarylethene unit at the same time, and thus has the photochromic and electrochromic functions at the same time. The triphenylamine group and the diarylethene group are connected through a covalent bond, the characters of the two groups are not affected by each other, and the development of respective characters is assisted. If the compound is applied to the storage filed, an electrochromic open / close state is increased on the basis of photochromic open / close state, so that the storage capacity is doubled without increasing any storage medium. The bifunctional compound and preparation method thereof have an important theory and actual meaning for the researches on storage devices and switch devices.

Description

technical field [0001] The invention belongs to the field of organic functional materials, in particular to a dual-functional compound with photochromism and electrochromism and a preparation method. Background technique [0002] Photochromism refers to the discoloration of light as an external excitation source. Generally speaking, it means that a material can undergo a specific chemical reaction or physical effect under the irradiation of light of an appropriate wavelength, and change from one form to another due to structural changes. The absorption spectrum changes significantly, and under the action of another wavelength of light or heat, the material can return to its original form. Materials with photochromic properties are photochromic materials. Organic photochromic materials include: fulgid anhydride, spiropyran, Schiff base, diarylethene, etc. It is mainly used in optical storage, optical switches, protective and decorative materials, anti-counterfeiting materia...

Claims

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Application Information

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IPC IPC(8): C07D333/20C07D333/28C09K9/02G02F1/15
CPCC07D333/20C07D333/28C09K9/02C09K2211/1022G02F1/0009G02F1/15
Inventor 李祥高金会义王志强王世荣肖殷
Owner TIANJIN UNIV
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