Scholl Reaction of ortho-Phenylene-Bridged Cyclic Pyrrole-Thiophene Hybrid Hexamer
Scholl Reaction of ortho-Phenylene-Bridged Cyclic Pyrrole-Thiophene Hybrid Hexamer
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DOI：
10.1055/a-1577-7972
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发表时间：
2021-08
期刊：
影响因子：
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通讯作者：
Takayuki Tanaka;Yusuke Matsuo;A. Osuka
中科院分区：
文献类型：
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作者：
Takayuki Tanaka;Yusuke Matsuo;A. Osuka
邻苯撑桥联的环状吡咯噻吩杂环六聚体的Scholl反应以45%的产率得到了环蕃型[5]杂螺烯。通过X射线衍射分析明确地揭示了结构。该化合物具有尖锐的吸收光谱和荧光光谱，反映了其刚性结构。基于密度泛函理论计算分析了反应路径，发现[5]螺旋烯二聚体的形成是有利的，而进一步的氧化由于应变能的增加而被抑制.
Abstract The Scholl reaction of ortho-phenylene-bridged cyclic pyrrole-thiophene hybrid hexamer gave cyclophane-type [5]heterohelicene exclusively in 45% yield. The structure was unambiguously revealed by X-ray diffraction analysis. This helicenophane-type compound showed sharp absorption and fluorescence spectra, reflecting its rigid structure. The reaction path was analyzed on the basis of DFT calculations, and it was found that the formation of the [5]helicene-dimer is thermodynamically favored and further oxidation is prohibited due to the increased strain energy.