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A Phenylene-Bridged Cyclohexa-meta-phenylene as Hexa-peri-hexabenzocoronene Precursor
Bastian Dumslaff1, Manfred Wagner1, Dieter Schollmeyer2
1Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany.
Abstract:
A phenylene-bridged cyclohexa-meta-phenylene was synthesized via intramolecular Yamamoto coupling of an appropriate p-quinquephenyl derivative carrying four m-chlorophenyl substituents. The structural proof could be obtained by single-crystal X-ray diffraction analysis, which also revealed a slightly strained structure with an internal phenylene bridge. Notably, this cyclo-meta-phenylene served as a novel precursor for hexa-peri-hexabenzocoronene (HBC). The cyclodehydrogenation proceeded smoothly, providing the corresponding HBC derivative as confirmed by MALDI-TOF-MS, and UV/Vis spectroscopy.
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