Regio-selective substitution at the 1,3- and 6,8-positions of pyrene for the construction of small dipolar molecules

Feng, Xing; Tomiyasu, Hirotsugu; Hu, Jian-Yong; Wei, Xianfu; Redshaw, Carl; Elsegood, Mark R. J.; Horsburgh, Lynne; Teat, Simon J.; Yamato, Takehiko

Abstract

© 2015 American Chemical Society. This article presents a novel asymmetrical functionalization strategy for the construction of dipolar molecules via efficient regioselective functionalization along the Z-axis of pyrene at both the 1,3- and 6,8-positions. Three asymmetrical ly substituted 1,3-diphenyl-6,8-R-disubsituted pyrenes were fully characterized by X-ray crystallography, photophysical properties, electrochemistry, and density functional theory calculations.

Citation

Feng, X., Tomiyasu, H., Hu, J.-Y., Wei, X., Redshaw, C., Elsegood, M. R. J., Horsburgh, L., Teat, S. J., & Yamato, T. (2015). Regio-selective substitution at the 1,3- and 6,8-positions of pyrene for the construction of small dipolar molecules. Journal of Organic Chemistry, 80(21), 10973-10978. https://doi.org/10.1021/acs.joc.5b02128

• Journal Article Type: Article
• Acceptance Date: Sep 10, 2015
• Online Publication Date: Oct 14, 2015
• Publication Date: Nov 6, 2015
• Deposit Date: Mar 14, 2016
• Publicly Available Date: Mar 14, 2016
• Journal: Journal of organic chemistry
• Print ISSN: 0022-3263
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 80
• Issue: 21
• Pages: 10973-10978
• DOI: https://doi.org/10.1021/acs.joc.5b02128
• Keywords: Dipolar molecules; Regioselective functionalization
• Public URL: https://hull-repository.worktribe.com/output/412902
• Publisher URL: http://pubs.acs.org/doi/10.1021/acs.joc.5b02128
• Additional Information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see 10.1021/acs.joc.5b02128
• Contract Date: Mar 14, 2016