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

Clarke, Rebecca; Ho, Kin Lok; Alsimaree, Abdulrahman Abdullah; Woodford, Owen J.; Waddell, Paul G.; Bogaerts, Jonathan; Herrebout, Wouter; Knight, Julian G.; Pal, Robert; Penfold, Thomas J.; Hall, Michael J.

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


Authors

Rebecca Clarke

Kin Lok Ho

Abdulrahman Abdullah Alsimaree

Owen J. Woodford

Paul G. Waddell

Jonathan Bogaerts

Wouter Herrebout

Julian G. Knight

Thomas J. Penfold

Michael J. Hall



Abstract

Chiral organic fluorophores have significant promise in the development of efficient emitters of circularly polarized light. Herein we describe a helically chiral boron dipyrromethene (BODIPY) with a hitherto unreported N,N,O,C-boron-chelation motif, synthesised by means of a one-pot boron metathesis, nucleophilic aromatic substitution (SNAr), Suzuki coupling, boron chelation, cascade reaction. Resolution of the racemic BODIPY (by preparative HPLC on a chiral stationary phase) allowed examination of the chiroptical properties of the resulting enantiomers (λmax(abs)=593 nm, λmax(em)=622 nm, ϵ=30 000 m−1 cm−1, φF=0.49, |glum|=3.7×10−3 (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.

Citation

Clarke, R., Ho, K. L., Alsimaree, A. A., Woodford, O. J., Waddell, P. G., Bogaerts, J., …Hall, M. J. (2017). Circularly Polarised Luminescence from Helically Chiral “Confused” N,N,O,C-Boron-Chelated Dipyrromethenes (BODIPYs). ChemPhotoChem, 1(11), 513-517. https://doi.org/10.1002/cptc.201700106

Journal Article Type Article
Acceptance Date Jun 29, 2017
Online Publication Date Aug 16, 2017
Publication Date Aug 16, 2017
Deposit Date Feb 20, 2018
Publicly Available Date Aug 16, 2018
Journal ChemPhotoChem.
Print ISSN 2367-0932
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 1
Issue 11
Pages 513-517
DOI https://doi.org/10.1002/cptc.201700106

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Copyright Statement
This is the accepted version of the following article: Clarke, Rebecca, Ho, Kin Lok, Alsimaree, Abdulrahman Abdullah, Woodford, Owen J., Waddell, Paul G., Bogaerts, Jonathan, Herrebout, Wouter, Knight, Julian G., Pal, Robert, Penfold, Thomas J. & Hall, Michael J. (2017). Circularly Polarised Luminescence from Helically Chiral “Confused” N,N,O,C-Boron-Chelated Dipyrromethenes (BODIPYs). ChemPhotoChem 1(11): 513-517 which has been published in final form at https://doi.org/10.1002/cptc.201700106. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.





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