Azulene–Pyridine-Fused Heteroaromatics
Name
ja-2020-062996.R1_Proof_hi copy.pdf
Description
Accepted version
Size
548.97 KB
Format
Adobe PDF
Checksum (MD5)
8dc90589a8852c04f1548a2e6097bf24
Author(s)
Xin, Hanshen
Li, Jing
Lu, Ruqiang
Gao, Xike
Swager, Timothy M
Date Issued
July 2020
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Xin, Hanshen et al. "Azulene–Pyridine-Fused Heteroaromatics." Journal of the American Chemical Society 142, 31 (July 2020): 13598–13605 © 2020 American Chemical Society
Version
Author's final manuscript
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-Noncommercial-Share Alike
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/jacs.0c06299
