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.
Kin Lok Ho
Abdulrahman Abdullah Alsimaree
Owen J. Woodford
Paul G. Waddell
Julian G. Knight
Professor Robert Pal firstname.lastname@example.org
Thomas J. Penfold
Michael J. Hall
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.
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|
|Peer Reviewed||Peer Reviewed|
Accepted Journal Article
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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