Fukuda Hisatane, Amimoto Kiichi, Koyama Hiroyuki, Kawato Toshio
Department of Chemistry, Faculty of Sciences, Kyushu University, 4-2-1 Ropponmatsu, Chuo-ku, Fukuoka 810-8560, Japan.
Org Biomol Chem. 2003 May 7;1(9):1578-83. doi: 10.1039/b212295b.
N-(3,5-Dihalosalicylidene)-2,6-dialkylaniline derivatives were prepared and their structure and photochromic properties were investigated. From the X-ray crystallography, it was revealed that steric repulsion between the azomethine hydrogen atom and the alkyl groups at the 2,6-positions of the aniline ring lead to non-planar molecular structure, which was effective for the crystals to exhibit photochromism. The relationship between photochromicity and crystal packing of N-(3,5-dichlorosalicylidene)-2,6-dialkylanilines series was also discussed. The 2,6-dialkylaniline method was suggested to be applicable to the preparation of photochromic Schiff bases with various substituents in the salicylidene rings.
制备了N-(3,5-二卤代亚水杨基)-2,6-二烷基苯胺衍生物，并对其结构和光致变色性能进行了研究。通过X射线晶体学研究发现，甲亚胺氢原子与苯胺环2,6位上的烷基之间的空间排斥作用导致分子结构非平面化，这有利于晶体表现出光致变色性能。还讨论了N-(3,5-二氯亚水杨基)-2,6-二烷基苯胺系列的光致变色性与晶体堆积之间的关系。结果表明，2,6-二烷基苯胺法适用于制备水杨亚胺环上具有各种取代基的光致变色席夫碱。
