Graduate School of Science and Engineering, Ehime University , Matsuyama 790-8577, Japan.
Faculty of Textile Science and Technology, Shinshu University , Ueda 386-8567, Japan.
J Am Chem Soc. 2016 Jun 22;138(24):7540-3. doi: 10.1021/jacs.6b04941. Epub 2016 Jun 9.
An acenaphthylene-fused cyclo[10]pyrrole 1b was selectively synthesized via an oxidative coupling reaction of the corresponding 2,2'-bipyrrole with the appropriate dianion template, croconate anion. The structure of 1b as the isolated largest cyclo[n]pyrrole was elucidated by X-ray crystallographic analysis. The absorption spectrum exhibited a markedly red-shifted, intensified L band at 1982 nm, which was interpreted by application of Michl's perimeter and Gouterman's 4-orbital models, supported by magnetic circular dichroism (MCD) data and theoretical calculations.
通过相应的 2,2'-联吡啶与适当的二价阴离子模板,克罗酸阴离子的氧化偶联反应,选择性地合成了一个并环[10]吡咯 1b。1b 的结构作为分离出的最大环[n]吡咯通过 X 射线晶体学分析阐明。吸收光谱显示出明显红移、增强的 L 带,位于 1982nm,通过 Michl 的周长和 Gouterman 的 4-轨道模型的应用进行了解释,得到了磁圆二色性(MCD)数据和理论计算的支持。