Triangle-shaped polycyclic aromatics based on tribenzocoronene: facile synthesis and physical properties |
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Authors: | Zhongtao Li Nigel T Lucas |
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Institution: | a Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China b National Center for Nanoscience and Technology of China, Beijing 100080, PR China c School of Chemistry, The University of Sydney, NSW 2006, Australia |
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Abstract: | A series of triangle-shaped polycyclic aromatics have been developed according to a facile synthetic protocol with high yields. As revealed by X-ray single crystal data, their molecular conformation and packing arrangement are significantly influenced by the electronic properties and steric bulk of peripheral subunits. The ‘saddle’-shaped hexahalotribenzocoronenes (ClTBC and FTBC) possess C2 symmetric structures and can self-assemble into well-defined columnar structures, dramatically different from hexabutyoxytribenzocoronene (TBC), which adopts a C3 symmetric ‘double-concave’ structure and less efficient packing arrangement. In the compound trithiophenocoronene (TTC), the five-membered corner rings produce a more open bay-region periphery alleviating intramolecular steric congestion. As a result, the molecule adopts an almost planar conformation. |
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Keywords: | Polycyclic aromatics Packing arrangement Synthesis Physical properties |
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