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A Trithia‐Bridged N‐Heterotriangulene: The Hitherto Missing Electron Donor
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2024-12-16 , DOI: 10.1002/anie.202423802
Jan Borstelmann, Viktoria Gensch, Dominik Fehn, Matthias E. Miehlich, Frank Hampel, Frank Rominger, Karsten Meyer, Milan Kivala

The very first representative of trithia‐bridged N‐heterotriangulene, a triphenylamine with sulfur atoms bridging the ortho‐positions, was synthesized by a sequence of regioselective sulfenylation with phthalimidesulfenyl chloride followed by Lewis acid‐catalyzed electrophilic cyclization. X‐ray crystallography revealed a saddle‐shaped geometry of the polycyclic scaffold. UV/Vis absorption spectroscopy and cyclic voltammetry were used to characterize the optoelectronic properties. The title compound is a particularly strong electron donor forming a perfectly stable radical cation, which was analyzed by electron paramagnetic resonance spectroscopy and X‐ray crystallography. The electron donor properties were further highlighted by the formation of crystalline donor‐acceptor complexes with strong cyano‐based acceptors.

中文翻译:


三硫桥接的 N-异质三角化合物:迄今为止缺失的电子供体



三硫桥 N-异质三安乙烯的第一个代表,一种具有硫原子桥接正位的三苯胺,是通过与邻苯二甲酰亚胺二氯进行区域选择性亚磺酰化,然后是路易斯酸催化的亲电环化序列合成的。X 射线晶体学揭示了多环支架的马鞍形几何形状。紫外/可见光吸收光谱法和循环伏安法用于表征光电特性。标题化合物是一种特别强的电子供体,形成完全稳定的自由基阳离子,通过电子顺磁共振光谱和 X 射线晶体学对其进行分析。通过与强氰基受体形成结晶供体-受体复合物,进一步突出了电子供体特性。
更新日期:2024-12-16
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