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Circularly polarised luminescence from helically chiral “confused” N,N,O,C-Boron-Chelated Dipyrromethenes (BODIPYs).

Clarke, Rebecca and Ho, Kin Lok and Alsimaree, Abdulrahman Abdullah and Woodford, Owen J. and Waddell, Paul G. and Bogaerts, Jonathan and Herrebout, Wouter and Knight, Julian G. and Pal, Robert and Penfold, Thomas J. and Hall, Michael J. (2017) 'Circularly polarised luminescence from helically chiral “confused” N,N,O,C-Boron-Chelated Dipyrromethenes (BODIPYs).', ChemPhotoChem., 1 (11). pp. 513-517.


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.

Item Type:Article
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Publisher 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 This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
Date accepted:29 June 2017
Date deposited:20 February 2018
Date of first online publication:16 August 2017
Date first made open access:16 August 2018

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