A Study of 1,2-Dihydro-1,2-azaborine in a π-Conjugated System†
A Study of 1,2-Dihydro-1,2-azaborine in a π-Conjugated System†
复制标题
DOI：
10.1021/om100408m
复制
发表时间：
2010-07
期刊：
影响因子：
2.8
通讯作者：
T. Taniguchi;S. Yamaguchi
中科院分区：
文献类型：
--
作者：
T. Taniguchi;S. Yamaguchi
N-Boc保护的双（5-苯基-2-吡咯基）硼烷与BF_3·OEt_2反应，以中等产率得到3-（苯基吡咯基）-6-苯基-1，2-二氢-1，2-氮杂硼杂环戊烯。与苯类似物相比，该化合物在更长的波长处显示出吸收带，并且还表现出强烈的红移荧光，具有接近1的高量子产率。根据X-射线结构分析、循环伏安法和理论计算，1，2-二氢-1，2-氮杂硼杂环在扩展的π共轭骨架中不像苯类似物，而像环己二烯类似物。
The reaction of N-Boc-protected bis(5-phenyl-2-pyrrolyl)borane with BF3·OEt2 produced 3-(phenylpyrrolyl)-6-phenyl-1,2-dihydro-1,2-azaborine in moderate yield. This compound showed an absorption band at a longer wavelength compared to that of its benzene analogue and also exhibited an intense red-shifted fluorescence with a high quantum yield close to unity. According to the X-ray structural analysis, cyclic voltammetry, and theoretical calculations, the 1,2-dihydro-1,2-azaborine acts not like a benzene analogue but like a cyclohexadiene analogue in the extended π-conjugated skeleton.