EXPERIMENTAL AND THEORETICAL-STUDY OF NEAR-INFRARED ABSORBING NAPHTHOQUINONE METHIDE DYES WITH A NONPLANAR GEOMETRY

被引：46

作者：

KUBO, Y ^{[1
]}

YOSHIDA, K ^{[1
]}

ADACHI, M ^{[1
]}

NAKAMURA, S ^{[1
]}

MAEDA, S ^{[1
]}

机构：

[1] MITSUBISHI KASEI CORP,RES CTR,MIDORI KU,YOKOHAMA 227,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 08期

关键词：

D O I：

10.1021/ja00008a012

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The bathochromic shift of the near-infrared absorption spectra of naphthoquinone methide dyes has been observed as a function of increased steric hindrance between the quinone imine and aniline segments. This novel shift that results from the loss of planarity has been examined by means of semiempirical INDO/S and AM1 models. Based on the configuration interaction (CI) analysis, the observed transitions in both the near-infrared and UV regions have been assigned. The introduction of an acetylamino group at the 2-position of aniline ring has caused a bathochromic shift with a remarkable increase in molecular extinction coefficient. In order to interpret these results, both an electronic factor and a steric effect have been analyzed. This interesting color-structure relationship of a nonplanar chromophoric system has been elucidated.

引用

页码：2868 / 2873

页数：6

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