SYNTHESIS AND OPTICAL PROPERTIES OF 2,2′-BIIMIDAZOLE AND BENZO[d]IMIDAZOLE DERIVATIVES: CHANGING π-CONJUGATION BY PHOTOEXCITATION

被引：4

作者：

Matsumoto, Shoji ^{[1
]}

Zhao, Yu ^{[1
]}

Akazome, Motohiro ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Engn, Dept Appl Chem & Biotechnol, Inage Ku, Chiba 2638522, Japan

来源：

HETEROCYCLES | 2014年 / 88卷 / 01期

关键词：

Imidazole; Benzo[d]imidazole; Photoexcitation; Stokes Shift; Dihedral Angle; INTRAMOLECULAR CHARGE-TRANSFER; CRYSTAL-STRUCTURES; ME(2)BIIM-BRIDGED DINUCLEAR; ARYL HALIDES; N-ARYLATION; DIARYLETHENE; COMPLEXES; CONSTRUCTION; CYTOTOXICITY; FLUORESCENCE;

D O I：

10.3987/COM-13-S(S)12

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,1',5,5'-Tetraaryl-2,2'-biimidazole and benzo [d] imidazole derivatives were synthesized. Symmetrical and unsymmetrical benzo[d]imidazole derivatives could be obtained by the Pd-catalyzed coupling reaction between 2-iodo-benzo[d]imidazole and the corresponding (benzo)imidazole anion. Hypsochromic shifts in absorption and fluorescence spectra of 1,1',5,5'-tetraaryl-2,2'-biazole were observed by switching pyrrole rings for imidazole and benzo[d]imidazole rings, resulting in compounds with various Stokes shifts. Based on the (TD)DFT calculation, it was reasoned that changing the conformation of each single bond from a twisted to planar structure by photoexcitation led to larger Stokes shifts.

引用

页码：261 / 273

页数：13

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