CN106349146A - 一种新型光致变色材料的合成方法 - Google Patents

一种新型光致变色材料的合成方法 Download PDF

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CN106349146A
CN106349146A CN201610655602.XA CN201610655602A CN106349146A CN 106349146 A CN106349146 A CN 106349146A CN 201610655602 A CN201610655602 A CN 201610655602A CN 106349146 A CN106349146 A CN 106349146A
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ethyl
5mmol
indoline
alcohol
photochromic material
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潘忠宁
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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Abstract

一种新型光致变色材料的合成方法，在氩气的保护下，将2，3，3－三甲基－Ｎ－乙基亚硫酸化吲哚啉（5mmol）与５－甲基水杨醛（5mmol）混合在100ｍＬ三颈烧瓶中，加入20mL无水乙醇使之完全溶解；再加入0.5mL六氢吡啶，加热回流，反应1～2ｈ，溶液由无色变为红色，停止反应，将过量乙醇旋出；最后用少量乙醇重结晶，得红色晶体，1－乙基－2－（2－羟基－5－甲基苯乙烯基）－3，3－二甲基－3Ｈ－吲哚啉。本发明的有益效果是：合成工艺简单，反应条件温和，生产成本较低，可重复性好。

Description

一种新型光致变色材料的合成方法
技术领域
本发明涉及材料合成方法，具体的是一种新型光致变色材料的合成方法。
背景技术
20世纪50年代， Hirshbergt等提出光致变色的概念，指出光成色与光漂白的循环可构成化学记忆模型，从而使光致变色材料用于光信息存储。光致变色反应材料是一个依靠光激发来改变吸收性质的材料，在激发撤除以后，诱导变色能力仍能保留。因此能在热作用条件下或在相应诱导吸收的光激发下返回原始状态。同时，光致变色材料具有可逆的行为，可以导致颜色的改变。 变色材料种类较多，结构也千差万别，有无机材料也有有机材料。有机光致变色化合物种类较多，如俘精酸酐类化合物、二芳基乙烯类化合物、席夫碱类化合物、吡喃类化合物以及螺吡喃和螺噁嗪类化合物等。有些有机光致材料已经开始了工业化。本研究以吲哚啉为母体设计合成了一种新型光致变色材料。
发明内容
本发明所要解决的技术问题在于提供一种新型光致变色材料的合成方法，提供一种新的合成方法。
本发明采用的合成方法，包括如下步骤：
a、在氩气的保护下，将2，3，3－三甲基－Ｎ－乙基亚硫酸化吲哚啉（5mmol）与５－甲基水杨醛（5mmol）混合在100ｍＬ三颈烧瓶中，加入20mL无水乙醇使之完全溶解；
b、再加入0.5mL六氢吡啶，加热至回流，反应1～2ｈ，溶液由无色变为红
色，停止反应，将过量乙醇旋出；
c、最后用乙醇重结晶，得红色晶体，1－乙基－2－（2－羟基－5－甲基苯乙烯基）－3，3－二甲基－3Ｈ－吲哚啉。
本发明的有益效果是：合成工艺简单，反应条件温和，生产成本较低，可重复性好。
具体实施方式
以下结合实例进一步说明本发明的内容，由技术常识可知，本发明也可通过其它的不脱离本发明技术特征的方案来描述，因此所有在本发明范围内或等同本发明范围内的改变均被本发明包含。
实施例：在氩气的保护下，将2，3，3－三甲基－Ｎ－乙基亚硫酸化吲哚啉（5mmol）与５－甲基水杨醛（5mmol）混合在100ｍＬ三颈烧瓶中，加入20mL无水乙醇使之完全溶解；再加入0.5mL六氢吡啶，加热回流，反应1～2ｈ，溶液由无色变为红色，停止反应，将过量乙醇旋出；最后用少量乙醇重结晶，得红色晶体，1－乙基－2－（2－羟基－5－甲基苯乙烯基）－3，3－二甲基－3Ｈ－吲哚啉。
光照前最大吸收在450ｎｍ处，而且从250～520ｎｍ均有吸收，吸收带相对较宽。

Claims (1)

1.一种新型光致变色材料的合成方法，包括如下步骤：
a、在氩气的保护下，将2，3，3－三甲基－Ｎ－乙基亚硫酸化吲哚啉（5mmol）与５－甲基水杨醛（5mmol）混合在100ｍＬ三颈烧瓶中，加入20mL无水乙醇使之完全溶解；
再加入0.5mL六氢吡啶，加热回流，反应1～2ｈ，溶液由无色变为红色，
停止反应，将过量乙醇旋出；
b、最后用少量乙醇重结晶，得红色晶体，1－乙基－2－（2－羟基－5－甲基苯乙烯基）－c，3－二甲基－3Ｈ－吲哚啉。
CN201610655602.XA 2016-08-11 2016-08-11 一种新型光致变色材料的合成方法 Pending CN106349146A (zh)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0483542A1 (en) * 1990-10-05 1992-05-06 Matsushita Electric Industrial Co., Ltd. A photochromic material and an optical storage medium using the same
EP0517055A1 (en) * 1991-06-06 1992-12-09 Bayer Corporation Merocyanine protein error indicators
US5279790A (en) * 1991-06-06 1994-01-18 Miles Inc. Merocyanine and nitro or nitroso substituted polyhalogenated phenolsulfonephthaleins as protein indicators in biological samples
CN105154065A (zh) * 2015-08-19 2015-12-16 济南大学 一种快速专一性识别羟基自由基的荧光探针及其制备方法和应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0483542A1 (en) * 1990-10-05 1992-05-06 Matsushita Electric Industrial Co., Ltd. A photochromic material and an optical storage medium using the same
EP0517055A1 (en) * 1991-06-06 1992-12-09 Bayer Corporation Merocyanine protein error indicators
US5279790A (en) * 1991-06-06 1994-01-18 Miles Inc. Merocyanine and nitro or nitroso substituted polyhalogenated phenolsulfonephthaleins as protein indicators in biological samples
CN105154065A (zh) * 2015-08-19 2015-12-16 济南大学 一种快速专一性识别羟基自由基的荧光探针及其制备方法和应用

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
REDA M. EL-SHISHTAWY,等: "Photophysical Studies of a New Water Soluble Indocarbocyanine Dye Adsorbed onto Microcrystalline Cellulose and β-Cyclodextrin", 《MOLECULES》 *
SHUJUAN LIU,等: "Development of Upconversion Luminescent Probe for Ratiometric Sensing and Bioimaging of Hydrogen Sulfide", 《ACS APPLIED MATERIALS & INTERFACES》 *
SHYAMAPROSAD GOSWAMI,等: "Carbazole based hemicyanine dye for both "naked eye"and ‘NIR’fluorescence detection of CN- in aqueous solution:from molecules to low cost devices (TLC plate sticks)", 《DALTON TRANSACTIONS》 *
YONGKANG YUE,等: "A Dual Colorimetric/Fluorescence System for Determining pH Based on the Nucleophilic Addition Reaction of an o-Hydroxymerocyanine Dye", 《CHEMISTRY A EUROPEAN JOURNAL COMMUNICATION》 *

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