Author(s)Xin, Hanshen; Li, Jing; Lu, Ruqiang; Gao, Xike; Swager, Timothy M
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Azulene, a nonbenzenoid bicyclic aromatic hydrocarbon with unique electronic structure, is a promising building block for constructing nonbenzenoid π-conjugated systems. However, azulene-fused (hetero)aromatics remain rare as a result of limited synthetic methods. We report herein the unexpected synthesis of azulene- and pyridine-fused heteroaromatics Az-Py-1, a seven fused ring system with 30πelectrons, by reductive cyclization of a 1-nitroazulene. The structure of Az-Py-1 was unambiguously confirmed by single-crystal X-ray analysis, and analogues Az-Py-2-Az-Py-6 were also synthesized, demonstrating that this is an effective method for constructing azulene- and pyridine-fused heteroaromatics. Theoretical calculations and photophysical and electrochemical studies of Az-Py-1-Az-Py-6 suggest their potential as semiconductors, and the single-crystal ribbons of Az-Py-1 show high hole mobilities up to 0.29 cm2 V-1 s-1.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Journal of the American Chemical Society
American Chemical Society (ACS)
Xin, Hanshen et al. "Azulene–Pyridine-Fused Heteroaromatics." Journal of the American Chemical Society 142, 31 (July 2020): 13598–13605 © 2020 American Chemical Society
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