多态π开关：一种含有三个可切换稠合二氢芘单元的分子的合成与光化学

Multistate pi switches: synthesis and photochemistry of a molecule containing three switchable annelated dihydropyrene units.

作者信息

Mitchell Reginald H, Bohne Cornelia, Wang Yunxia, Bandyopadhyay Subhajit, Wozniak Chelsea B

机构信息

Department of Chemistry, University of Victoria, PO Box 3065, Victoria, BC, Canada, V8W 3V6.

出版信息

J Org Chem. 2006 Jan 6;71(1):327-36. doi: 10.1021/jo052153g.

DOI:10.1021/jo052153g

PMID:16388652

Abstract

[structure: see text] The synthesis of the multistate photochromic switch 3 is described. This switch contains three dihydropyrene (DHP) units in the most conjugated fully closed form 3-c,c,c. The thermally stable form has the central DHP unit open and is 3-c,o,c. NMR and laser flash photolysis experiments were used to characterize the multiple states in the photoswitching of 3 by visible and UV light. Three of the possible five isomeric states of 3-c,o,c were observed. Irradiation of 3-c,o,c by visible light led to the formation of 3-o,o,o via the isomer 3-c,o,o as an intermediate, which were observed by NMR. Irradiation by UV light led to the formation of 3-c,c,c, which decays with a lifetime of 7.5 ms.

摘要

[结构：见文本] 描述了多态光致变色开关3的合成。该开关在最共轭的完全闭合形式3-c,c,c中包含三个二氢芘（DHP）单元。热稳定形式的中心DHP单元是开放的，为3-c,o,c。核磁共振（NMR）和激光闪光光解实验用于表征3在可见光和紫外光作用下光开关过程中的多个状态。观察到了3-c,o,c的五种可能异构体状态中的三种。用可见光照射3-c,o,c会通过异构体3-c,o,o作为中间体形成3-o,o,o，这通过核磁共振得以观察到。用紫外光照射会形成3-c,c,c，其以7.5毫秒的寿命衰减。