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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, Kin Lok Ho, Abdu Alsimaree, Dr Paul Waddell, Dr Julian Knight, Dr Thomas Penfold, Dr Michael Hall

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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 (SNAr), 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 (lmax(abs) = 593 nm, lmax(em) = 622 nm, e = 30,000 M-1 cm-1, fF = 0.49, │glum│ = 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

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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