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Dye changing colour resulting from photo, acid, and its method of synthesis and dyeing

A photochromic and dye technology, applied in the direction of styrene-based dyes, can solve the problem of poor stability and achieve the effect of simple synthesis and unique structure

Inactive Publication Date: 2005-05-25
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some spiropyran compounds are photochromic and show yellow color, generally speaking, their stability is far less than that of diarylvinyl compounds (1, K.Uchida and M.Irie, Chem.Lett., 1995 , 969.2, R.Matsushima, H.Morikane and Y.Kohno, Chem.Lett., 2003, 32, 302.3, Y.Yokoyama, T.Serizawa, S.Suzuki, Y.Yokoyama and Y.Kurita, Chem.Lett., 1995, 17.4, M.Uchida, M.Kume and M.Irie, Bull, Chem.Soc.Jpn., 1996, 69, 1023.)
In addition, although the photochromic properties of diarylethylene compounds have been widely studied, their acid-induced chromic properties have not been involved at home and abroad.

Method used

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  • Dye changing colour resulting from photo, acid, and its method of synthesis and dyeing
  • Dye changing colour resulting from photo, acid, and its method of synthesis and dyeing
  • Dye changing colour resulting from photo, acid, and its method of synthesis and dyeing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of 3,4-bis-(2,4,5-trimethyl-3-thiophene)-2,5-diylidene aminopyrroline:

[0037]

[0038] Dissolve 0.32 g of 1,2-dicyano-1,2-bis(2,4,5-trimethyl-3-thiophene)ethylene in 50 ml of ethanol, add a catalytic amount of NaOCH 2 h 5 ., Ammonia gas was introduced at room temperature. Maintain the reaction for about 2 hours, remove the solvent by rotary evaporation, and use CCl 4 After recrystallization, 0.3 g of the product was obtained with a yield of 87%.

[0039] Mass Spectrum: 343[M + ]; NMR 1 H spectrum (500MHz, CDCl 3 , ppm): 2.50-3.50 (s, 3H), 2.25 (S, 6H), 2.09 (s, 3H), 2.08 (s, 3H), 1.79 (s, 3H), 1.77 (s, 3H); 13 C-NMR (250MHz, CDCl 3 ,ppm): 166.37,135.80,134.88,131.82,130.94,127.84,14.18,13.17,12.99; .

Embodiment 2

[0041] Synthesis of 3,4-bis(2,5-dimethyl-3-thiophene)-2,5-dibutyliminopyrroline

[0042]

[0043] Dissolve 0.31 g of 1,2-dicyano-1,2-bis-(2,5-dimethyl-3-thiophene)-ethylene in 40 ml of ethanol, add a catalytic amount of NaOCH 2 h 5 , Ammonia gas was introduced at room temperature. Maintain the reaction for about 2 hours, remove ethanol by rotary evaporation, and use CCl 4 Recrystallized to obtain 0.28g of the product. Yield 85%.

[0044] 0.17g of the compound synthesized above and 0.15g of n-butylamine were dissolved in n-butanol, heated to reflux, the reaction continued for 24 hours, and 0.33g of product was obtained by rotary evaporation, with a yield of 75%.

[0045] Mass spectrometry (M + ): Calculated, 427.67; Measured: 427.5; NMR 1 H spectrum (500MHz, CDCl 3 , ppm): 6.38(s, 2H), 2.40(s, 12H), 1.30-1.41(m, 12H), 0.97(t, 6H).

Embodiment 3

[0047] Synthesis of 3,4-bis-3-thiophene-2,5-dodecyl-diiminopyrroline

[0048]

[0049] Dissolve 0.29 g of 1,2-dicyano-1,2-bis-(thiophene-3)ethylene in 100 ml of dichloromethane, add 0.1 g of Na, and blow ammonia gas at room temperature. The reaction was maintained for 0.5 hours, and then the temperature was raised to 40°C. After the reaction was completed, the solvent was removed by rotary evaporation, and recrystallized with n-butanol to obtain 0.28 g of the product.

[0050] The compound 0.15 synthesized above and 1 g of n-dodecylamine were dissolved in n-butanol, heated to reflux, the reaction was continued for 48 hours, and 0.21 g of the product was obtained by rotary evaporation.

[0051] Mass spectrometry (M + ): Calculated, 595.99; Measured: 560.2; NMR 1 H spectrum (500MHz, CDCl 3 , ppm): 7.25 (d, 2H), 7.23 (s, 2H), 7.11 (d, 2H), 1.28-1.35 (m, 22H), 0.95 (t, 6H).

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Abstract

The present invention relates to a diarylvinyl yellow functional dye with photochromic and acid-induced chromatic properties and its synthesis and discoloration method. The functional dye is 3,4-bis(substituted five-membered heterocycle)-2,5- Diiminopyrroline compounds, which use 1,2-dicyano-1,2-bis(substituted five-membered heterocycle) vinyl compounds as raw materials, and under the action of catalysts and ammonia compounds in polar solvents Prepared by reaction. The prepared compound changes from colorless to yellow under the action of acid or light, and can undergo multiple reversible cycles. Taking advantage of this performance, this type of compound can be used as light-controlled rewritable full-color printing or full-color display, pH meter, light and chemical switch, light-controlled reversible discoloration device, and dual mode of acid-induced color and photochromic For high-density information recording, etc.

Description

technical field [0001] The invention relates to a photochromic and acid-induced chromic functional dye and its synthesis and color-changing method, in particular to a diarylethylene yellow functional dye with photo- and acid-induced chromic performance and its synthesis and color-changing method. Background technique [0002] In recent years, research on photochromic compounds as advanced materials has attracted much attention at home and abroad (1, H.B-Laurent and H.Dürr, Pure Appl.Chem., 2001, 73, 639.2, H.Dürr, and H.B-Laurent , "Photochromism: Molecules and Systems," Elsevier, Oxford (1990). 3, G. Berkovic, V. Krongauz and V. Weiss, Chem. Rev., 2000, 100, 1741. 4, M. Matumoto, D. Miyazaki and M . Tanaka, J. Am. Chem. Soc., 1998, 120, 1479.). Among them, the research and development of diarylethylene compounds is the most active. Trace it to its cause, be because this class compound has good fatigue resistance, thermal stability and higher quantum yield (1, Tyler B.Nors...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/14
Inventor 田禾罗千福李晓川朱为宏
Owner EAST CHINA UNIV OF SCI & TECH
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