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Near-Infrared Circularly Polarised Luminescence from Helically Extended Chiral N,N,O,O -Boron Chelated Dipyrromethenes

Algoazy, Nawaf; Clarke, Rebecca G.; Penfold, Thomas J.; Waddell, Paul G.; Probert, Michael R.; Aerts, Roy; Herrebout, Wouter; Stachelek, Patrycja; Pal, Robert; Hall, Michael J.; Knight, Julian G.

Near-Infrared Circularly Polarised Luminescence from Helically Extended Chiral N,N,O,O -Boron Chelated Dipyrromethenes Thumbnail


Authors

Nawaf Algoazy

Rebecca G. Clarke

Thomas J. Penfold

Paul G. Waddell

Michael R. Probert

Roy Aerts

Wouter Herrebout

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Dr Patrycja Brook patrycja.stachelek@durham.ac.uk
Royal Society University Research Fellow

Michael J. Hall

Julian G. Knight



Abstract

Synthetically straightforward π-extension of helically chiral N,N,O,O-boron chelated borondipyrromethenes (BODIPYs) has been achieved by incorporation of naphthyl rings into the BODIPY 3- and 5-positions. The effect of this extension on the photophysical and chiroptical properties is strongly dependent on the regiochemistry of the naphthyl substituents (4 exo, 4 lin, 4 endo). The most helicene-like regioisomer 4 endo is a near infra-red (NIR) emitter (λemmax=751 nm) with an emission band between 675–875 nm, displaying circularly polarised luminescence (CPL) with a luminescence dissymmetry factor, |glum|=5.7×10−3 and CPL brightness, BCPL=27, rivalling the best NIR CPL-emitting small organic molecules reported to date.

Citation

Algoazy, N., Clarke, R. G., Penfold, T. J., Waddell, P. G., Probert, M. R., Aerts, R., …Knight, J. G. (2022). Near-Infrared Circularly Polarised Luminescence from Helically Extended Chiral N,N,O,O -Boron Chelated Dipyrromethenes. ChemPhotoChem, 6(9), Article e202200090. https://doi.org/10.1002/cptc.202200090

Journal Article Type Article
Acceptance Date May 30, 2022
Online Publication Date Jun 30, 2022
Publication Date 2022-09
Deposit Date Jul 8, 2022
Publicly Available Date Feb 7, 2023
Journal ChemPhotoChem
Print ISSN 2367-0932
Electronic ISSN 2367-0932
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 6
Issue 9
Article Number e202200090
DOI https://doi.org/10.1002/cptc.202200090
Public URL https://durham-repository.worktribe.com/output/1199622

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Copyright Statement
© 2022 The Authors. ChemPhotoChem published by Wiley-VCH GmbH

This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.






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