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Red-Shifted Circularly Polarised Luminescence from Helically Chiral N,N,O,O-Boron Chelated Dipyrromethenes through Synthetically Facile meso-CF₃ Modification

Lookup NU author(s): Dr Aminah Almarshad, Dr Paul Waddell, Dr Casey Dixon, Aaron Campbell, Dr Roly ArmstrongORCiD, Professor Thomas PenfoldORCiD, Dr Julian Knight, Dr Michael HallORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

In the search for red-shifted small molecule emitters of circularly polarised light, a helically chiral N,N,O,O-boron chelated dipyrromethene (BODIPY) is described containing a meso-CF3 group, prepared in only two synthetic steps. The incorporation of an electron deficient substituent at the meso-position of a helically chiral BODIPY results in significant (~50 nm) red-shift of both the absorption (615 669 nm) and emission maxima (635 686 nm) in comparison to the parent compound, whilst maintaining a high extinction coefficient (83,000 mol-1 cm-1) and reasonable fluorescence quantum yield (0.30). Enantiomers were resolved by chiral stationary phase HPLC and absolute configuration assigned by the comparison of the experimental and calculated ECD spectra (gabs 3.6 × 10-3). A luminescence dissymmetry factor (glum 2.3 × 10-3) is reported, well supported by calculation (glum(calc) 2 × 10-3), resulting in an overall CPL brightness (BCPL = 29 M-1 cm-1) that is consummate with similar helically chiral monomeric BODIPYs. This work demonstrates the use electron deficient meso-CF3 groups in the development of red-shifted circularly polarised luminescent small organic molecules (CPL-SOMs), whilst maintaining their key chiroptical properties.

Publication metadata

Author(s): Almarshad AA, Waddell PG, Dixon C, Campbell A, Armstrong R, Levshov DI, Herrebout W, Penfold TJ, Black DJ, Pal R, de la Moya S, Knight JG, Hall MJ

Publication type: Article

Publication status: Published

Journal: Dyes and Pigments

Year: 2025

Pages: epub ahead of print

Online publication date: 26/12/2025

Acceptance date: 08/12/2025

Date deposited: 10/12/2025

ISSN (print): 0143-7208

ISSN (electronic): 1873-3743

Publisher: Elsevier Ltd

URL: https://doi.org/10.1016/j.dyepig.2025.113494

DOI: 10.1016/j.dyepig.2025.113494

Data Access Statement: Data will be made available on request.

Notes: preprint available at DOI: 10.26434/chemrxiv-2025-t9zsp https://chemrxiv.org/engage/chemrxiv/article-details/68845b71fc5f0acb52119c45 https://www.sciencedirect.com/science/article/pii/S0143720825008642

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