Unusual molecular conformations in fluorinated, contorted hexabenzocoronenes |
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Authors: | Loo Yueh-Lin Hiszpanski Anna M Kim Bumjung Wei Sujun Chiu Chien-Yang Steigerwald Michael L Nuckolls Colin |
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Institution: | Department of Chemical & Biological Engineering, Princeton University, Princeton, New Jersey 08544, United States. lloo@princeton.edu |
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Abstract: | Fluorinated, contorted hexabenzocoronenes (HBCs) have been synthesized in a facile manner via Suzuki-Miyaura coupling of fluorinated phenyl boronic acids followed by photocyclization and Scholl cyclization. In addition to the molecular conformation observed in previous HBC derivatives, close-contact fluorine-fluorine intramolecular interactions result in a metastable conformation not previously observed. Heating the metastable HBCs above 100 °C irreversibly converts them to the stable conformation, suggesting that the metastable conformation arises from a kinetically arrested state during cyclization. |
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