Lookup NU author(s): Rebecca Clarke,
Kin Lok Ho,
Dr Paul Waddell,
Dr Julian Knight,
Dr Thomas Penfold,
Dr Michael Hall
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.
For re-use rights please refer to the publisher's terms and conditions.
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.
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
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
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