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Iron(III) bromide catalyzed bromination of 2-tert-butylpyrene and corresponding position-dependent aryl-functionalized pyrene derivatives

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

Authors

Mark R. J. Elsegood

Xing Feng

Jian-Yong Hu

Hirotsugu Tomiyasu

Zhu Tao

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Jian Yong Hu

Mark R. J. Elsegood

Lynne Horsburgh

Simon J. Teat

Xian Fu Wei

Xian-Fu Wei

Takehiko Yamato



Abstract

The present work probes the bromination mechanism of 2-tert-butylpyrene (1), which regioselectively affords mono-, di-, tri- and tetra-bromopyrenes, by theoretical calculation and detailed experimental methods. The bromine atom may be directed to the K-region (positions 5- and 9-) instead of the more reactive 6- and 8-positions in the presence of iron powder. In this process, FeBr₃ plays a significant role to release steric hindrance or lower the activation energy of the rearrangement. The intermediate bromopyrene derivatives were isolated and confirmed by ¹H NMR spectrometry, mass spectroscopy and elemental analysis. Further evidence on substitution position originated from a series of aryl substituted pyrene derivatives, which were obtained from the corresponding bromopyrenes on reaction with 4-methoxy-phenylboronic acid by a Suzuki–Miyaura cross-coupling reaction. All position-dependent aryl-functionalized pyrene derivatives are characterized by single X-ray diffraction, ¹H/¹³C NMR, FT-IR and MS, and offered straightforward evidence to support our conclusion. Furthermore, the photophysical properties of a series of compounds were confirmed by fluorescence and absorption, as well as by fluorescence lifetime measurements.

Citation

Feng, X., Hu, J., Tomiyasu, H., Tao, Z., Redshaw, C., Elsegood, M. R. J., …Yamato, T. (2014). Iron(III) bromide catalyzed bromination of 2-tert-butylpyrene and corresponding position-dependent aryl-functionalized pyrene derivatives. RSC advances, 5(12), 8835-8848. https://doi.org/10.1039/C4RA12216J

Acceptance Date Dec 3, 2014
Online Publication Date Dec 4, 2014
Publication Date Dec 4, 2014
Deposit Date Jul 15, 2015
Publicly Available Date Jul 15, 2015
Journal RSC advances
Print ISSN 2046-2069
Electronic ISSN 2046-2069
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 5
Issue 12
Pages 8835-8848
DOI https://doi.org/10.1039/C4RA12216J
Keywords Iron(III) bromide; Bromination mechanism; Bromopyrenes; 2-tert-butylpyrene; Aryl-functionalized pyrene derivatives
Public URL https://hull-repository.worktribe.com/output/376453
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C4RA12216J#!divAbstract
Additional Information Author's accepted manuscript of an article which has been published in: RSC advances, 2015, v.5, issue 12.

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