Iwasaki Suzuka, Miyake Yusuke, Imoto Hiroaki, Naka Kensuke
Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan.
Materials Innovation Lab, Kyoto Institute of Technology Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan.
Chemistry. 2022 Nov 25;28(66):e202202084. doi: 10.1002/chem.202202084. Epub 2022 Sep 29.
Herein, we have synthesized a variety of cycloalkane-fused arsoles. Cyclopentane and cyclohexane were incorporated into the cycloalkane-fused arsoles. Surprisingly, cyclohexane-fused arsole 2 a gradually decomposed via oxidative ring-opening under ambient conditions, while cyclopentane-fused 1 a was stable. In addition, the Stokes shift of 2 a (7766 cm ) is larger than that of 1 a (5120 cm ). The effects of the fused cycloalkane on the stability and photophysical properties were attributed to the distortion of the cycloalkane. Computational calculations demonstrated that the cyclohexane moiety in 2 a was frustrated upon being incorporated into the rigid arsole ring, while the cyclopentane moiety in 1 a was much less distorted.
在此，我们合成了多种环烷并芳胂。环戊烷和环己烷被引入到环烷并芳胂中。令人惊讶的是，环己烷并芳胂2 a在环境条件下通过氧化开环逐渐分解，而环戊烷并芳胂1 a则是稳定的。此外，2 a的斯托克斯位移（7766 cm）大于1 a的斯托克斯位移（5120 cm）。稠合环烷对稳定性和光物理性质的影响归因于环烷的扭曲。计算结果表明，2 a中的环己烷部分在并入刚性芳胂环时受到阻碍，而1 a中的环戊烷部分扭曲程度小得多。
