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.

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., Herrebout, W., Stachelek, P., Pal, R., Hall, M. J., & 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