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NIR Circularly Polarised Luminescence from Helically-Extended Chiral N,N,O,O-Boron Chelated Dipyrromethenes

Lookup NU author(s): Nawaf Algoazy, Rebecca Clarke, Professor Thomas Penfold, Dr Paul Waddell, Professor Mike ProbertORCiD, Patrycja Stachelek, Dr Michael HallORCiD, Dr Julian Knight



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


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 (4exo, 4lin, 4endo). The most helicene-like regioisomer 4endo 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 x 10-3 and CPL brightness, BCPL = 27, rivalling the best NIR CPL-emitting small organic molecules reported to date.

Publication metadata

Author(s): Algoazy N, Clarke RG, Penfold TJ, Waddell PG, Probert MR, Aerts R, Herrebout W, Stachelek P, Pal R, Hall MJ, Knight JG

Publication type: Article

Publication status: Published

Journal: ChemPhotoChem

Year: 2022

Volume: 6

Issue: 9

Print publication date: 01/09/2022

Online publication date: 30/05/2022

Acceptance date: 30/05/2022

Date deposited: 03/06/2022

ISSN (electronic): 2367-0932

Publisher: Wiley-VCH


DOI: 10.1002/cptc.202200090


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Funder referenceFunder name
Flemish Government
Newcastle University
Saudi Arabian Cultural Bureau for financial support in the form of a King Abdullah Scholarship
Research Foundation - Flanders (FWO)