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Circularly Polarised Luminescence from Helically Chiral 'Confused' N,N,O,C-Boron-Chelated Dipyrromethenes (BODIPYs)

Lookup NU author(s): Rebecca Clarke, Dr Kin Lok Ho, Abdu Alsimaree, Dr Paul Waddell, Dr Julian Knight, Professor Thomas Penfold, Dr Michael HallORCiD

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This is the authors' accepted manuscript of an article that has been published in its final definitive form by Wiley - VCH Verlag GmbH & Co. KGaA, 2017.

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Abstract

Chiral organic fluorophores have significant promise in the development of efficient emitters of circularly polarized light. Herein we describe a helically chiral BODIPY with a hitherto unreported N,N,O,C-boron-chelation motif, synthesised via a one-pot boron metathesis, nucleophilic aromatic substitution (S_NAr), Suzuki coupling, boron chelation, cascade reaction. Resolution of the racemic BODIPY, by preparative chiral HPLC, allowed examination of the chiroptical properties of the resulting enantiomers (l_max(abs) = 593 nm, l_max(em) = 622 nm, e = 30,000 M^-1 cm^-1, f_F = 0.49, │g_lum│ = 3.7x10^-3 (hexane)). This is the first example of circularly polarised emission from a non-C₂ symmetric helically chiral N,N,O,C-BODIPY and as such provides a valuable benchmark for future developments in this compound series.

Publication metadata

Author(s): Clarke R, Ho KL, Alsimaree AA, Waddell PG, Bogaerts J, Herrebout W, Knight J, Pal R, Penfold T, Hall MJ

Publication type: Article

Publication status: Published

Journal: ChemPhotoChem

Year: 2017

Volume: 1

Issue: 11

Pages: 513-517

Print publication date: 01/11/2017

Online publication date: 19/07/2017

Acceptance date: 14/07/2017

Date deposited: 14/07/2017

ISSN (electronic): 2367-0932

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/cptc.201700106

DOI: 10.1002/cptc.201700106

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