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, Xian-Fu; Redshaw, Carl; Elsegood, Mark; Horsburgh, Lynne; Teat, Simon J.; Yamato, Takehiko

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

journal contribution

posted on 2015-11-09, 14:31 authored by Xing Feng, Hirotsugu Tomiyasu, Jian-Yong Hu, Xian-Fu Wei, Carl Redshaw, Mark ElsegoodMark Elsegood, Lynne Horsburgh, Simon J. Teat, Takehiko Yamato

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 asymmetrically substituted 1,3-diphenyl-6,8-R-disubsituted pyrenes were fully characterized by X-ray crystallography, photophysical properties, electrochemistry, and density functional theory calculations.

Funding

This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices (Institute for Materials Chemistry and Engineering, Kyushu University)”. We thank the EPSRC (travel grants to C.R.), The Royal Society of Chemistry, The Scientific Research Foundation for the Returned Overseas Chinese Scholars, the State Education Ministry, and The Scientific Research Common Program of Beijing Municipal Commission of Education (18190115/008) for financial support. The Advanced Light Source is supported by the Director, Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy under Contract DE-AC02-05CH11231.

History

School

Science

Department

Chemistry

Published in

Journal of Organic Chemistry

Citation

FENG, X. ... et al, 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), pp. 10973–10978.

Publisher

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2015

Notes

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: http://dx.doi.org/10.1021/acs.joc.5b02128