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

Lookup NU author(s): Rebecca Clarke, Jake Weatherston, Rafid Taj Aldeen, Dr Paul Waddell, Emeritus Professor William McFarlane, Professor Thomas Penfold, Dr Michael HallORCiD

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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, S N Ar, 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 (| g lum | from 2.1 to 3.7×10 -3 ; B CPL from 11.3 to 27.2).

Publication metadata

Author(s): Clarke RG, Weatherston J, Taj-Aldeen RA, Waddell PG, McFarlane W, Penfold TJ, Bogaerts J, Herrebout W, Mackenzie L, Pal R, Hall MJ

Publication type: Article

Publication status: Published

Journal: ChemPhotoChem

Year: 2023

Volume: 7

Issue: 1

Print publication date: 01/01/2023

Online publication date: 19/09/2022

Acceptance date: 16/09/2022

Date deposited: 14/09/2022

ISSN (electronic): 2367-0932

Publisher: Wiley-VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/cptc.202200194

DOI: 10.1002/cptc.202200194

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