Synthesis and photochromic properties of a dithiazolylindole
Synthesis and photochromic properties of a dithiazolylindole
复制标题
DOI：
10.1016/j.dyepig.2011.05.027
复制
发表时间：
2012-02
影响因子：
4.5
通讯作者：
Sayo Fukumoto;T. Nakashima;T. Kawai
中科院分区：
文献类型：
--
作者：
Sayo Fukumoto;T. Nakashima;T. Kawai
合成了一种新型光致变色化合物2，3-二噻唑吲哚，并对其光致变色性能进行了研究。该化合物在溶液和晶体中都表现出可逆的光致变色，在黑暗条件下没有自发漂白。在正己烷中，二硫杂吲哚的光环化量子产率高达83%，表明光反应构象是通过分子内相互作用稳定的。X-射线晶体结构分析表明，二硫杂吲哚在结晶态下以己三烯为中心呈准C2对称性的光反应构象。这种构象是通过推测中心N-甲基吲哚和侧链噻唑单元之间的分子内CH/N氢键以及反应中心碳上甲基之间的空间相互作用来实现的。~1H核磁共振变温研究也支持了溶液中分子内氢键的观点。
A novel photochromic 2,3-dithiazolylindole has been synthesized and its photochromic properties was elucidated. This compound showed reversible photochromism both in solution and in a crystal with no spontaneous bleaching under dark conditions. The photocyclization quantum yield of the dithiazolylindole was as high as 83% in hexane, suggesting the photoreactive conformation was stabilized through intramolecular interactions. X-ray crystal structure analysis revealed that the dithiazolylindole adopted the photoreactive conformation with quasi-C2symmetry around the hexatriene moiety in the crystalline state. This conformation was assisted by presumed intramolecular CH/N hydrogen bonding between the central N-methylindole and the side-chain thiazolyl units in combination with steric interactions between methyl groups at the reactive center carbons. The suggestion of intramolecular hydrogen bonding in solution was also supported by a1H NMR variable temperature study.