An orthogonal C–H borylation – cross-coupling strategy for the preparation of tetrasubstituted “A2B2”-chrysene derivatives with tuneable photophysical properties

K. W. J. Heard; J. J. Morrison; L. Weston; C. H. Lo; L. Pirvu; J. Raftery; M. S. Little; J. J. W. McDouall; S. G. Yeates; P. Quayle

doi:10.1039/C4CC10132D

An orthogonal C–H borylation – cross-coupling strategy for the preparation of tetrasubstituted “A₂B₂”-chrysene derivatives with tuneable photophysical properties†

K. W. J. Heard,^a J. J. Morrison,^a L. Weston,^a C. H. Lo,^a L. Pirvu,^a J. Raftery,^a M. S. Little,^a J. J. W. McDouall,^a S. G. Yeates*^a and P. Quayle*^a

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^a School of Chemistry, University of Manchester, Oxford Road, Manchester, UK
E-mail: peter.quayle@manchester.ac.uk

Abstract

The regioselective, orthogonal functionalisation of 4,10-dichlorochrysene enables the synthesis of a variety of 2,8,4,10-”A₂B₂”-tetrasubstituted chrysenes. Such compounds exhibit broadened UV-vis absorption spectra, decreased band gap and higher HOMO levels compared to the parent chrysene.

Chemical Communications

An orthogonal C–H borylation – cross-coupling strategy for the preparation of tetrasubstituted “A₂B₂”-chrysene derivatives with tuneable photophysical properties†

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An orthogonal C–H borylation – cross-coupling strategy for the preparation of tetrasubstituted “A₂B₂”-chrysene derivatives with tuneable photophysical properties

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