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Title: Iron(III) bromide catalyzed bromination of 2-tert-butylpyrene and corresponding position-dependent aryl-functionalized pyrene derivatives
Authors: Feng, Xing
Hu, Jian-Yong
Tomiyasu, Hirotsugu
Tao, Zhu
Redshaw, Carl
Elsegood, Mark R.J.
Horsburgh, Lynne
Teat, Simon J.
Wei, Xian-Fu
Yamato, Takehiko
Keywords: Polycyclic aromatic-hydrocarbons
Photophysical properties
Blue emmitters
Efficient
PI
Borylation
Substitution
Dendrimers
Issue Date: 2015
Publisher: © The Royal Society of Chemistry
Citation: FENG, X. ...et al., 2015. Iron(III) bromide catalyzed bromination of 2-tert-butylpyrene and corresponding position-dependent aryl-functionalized pyrene derivatives. RSC Advances, 5(12), pp.8835-8848.
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.
Description: This paper is closed access.
Version: Accepted for publication
DOI: 10.1039/c4ra12216j
URI: https://dspace.lboro.ac.uk/2134/18635
Publisher Link: http://dx.doi.org/10.1039/c4ra12216j
ISSN: 2046-2069
Appears in Collections:Closed Access (Chemistry)

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