Synthesis and Structural Diversification of Circularly Polarised Luminescence Active, Helically Chiral, “Confused” N,N,O,C‐BODIPYs**

Clarke, Rebecca G.; Weatherston, Jake; Taj‐Aldeen, Rafid A.; Waddell, Paul G.; McFarlane, William; Penfold, Thomas J.; Bogaerts, Jonathan; Herrebout, Wouter; Mackenzie, Lewis E.; Pal, Robert; Hall, Michael J.

Abstract

Helically chiral boron-chelated dipyrromethene (BODIPY) dyes are known to exhibit solution phase circularly polarized luminescence (CPL), but examples are limited to a few synthetically accessible molecular architectures. We report a B−N chelation, SNAr, Suzuki cross-coupling, B−O chelation cascade reaction for the synthesis of understudied helically chiral, N,N,O,C-boron chelated, “confused” BODIPYs, from readily accessible 3,5-dibromo-BODIPY starting materials. Using this approach we have prepared a series of helically chiral “confused” BODIPYs with variation of the 3,5-subsitutents. Following resolution by chiral HPLC, absolute stereochemistry was assigned through comparison of the experimental and calculated ECD spectra, and solution phase chiroptical properties including CPL were determined (|glum| from 2.1 to 3.7×10−3; BCPL from 11.3 to 27.2).

Citation

Clarke, R. G., Weatherston, J., Taj‐Aldeen, R. A., Waddell, P. G., McFarlane, W., Penfold, T. J., Bogaerts, J., Herrebout, W., Mackenzie, L. E., Pal, R., & Hall, M. J. (2023). Synthesis and Structural Diversification of Circularly Polarised Luminescence Active, Helically Chiral, “Confused” N,N,O,C‐BODIPYs**. ChemPhotoChem, 7(1), Article e202200194. https://doi.org/10.1002/cptc.202200194

• Journal Article Type: Article
• Acceptance Date: Sep 19, 2022
• Online Publication Date: Oct 18, 2022
• Publication Date: 2023-01
• Deposit Date: Jan 16, 2023
• Publicly Available Date: Mar 29, 2023
• Journal: ChemPhotoChem
• Print ISSN: 2367-0932
• Electronic ISSN: 2367-0932
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 7
• Issue: 1
• Article Number: e202200194
• DOI: https://doi.org/10.1002/cptc.202200194
• Public URL: https://durham-repository.worktribe.com/output/1183444