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

Algoazy, Nawaf and Clarke, Rebecca G. and Penfold, Thomas J. and Waddell, Paul G. and Probert, Michael R. and Aerts, Roy and Herrebout, Wouter and Stachelek, Patrycja and Pal, Robert and Hall, Michael J. and Knight, Julian G. (2022) 'Near-Infrared Circularly Polarised Luminescence from Helically Extended Chiral N,N,O,O -Boron Chelated Dipyrromethenes.', ChemPhotoChem, 6 (9). e202200090.


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.

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Publisher statement:© 2022 The Authors. ChemPhotoChem published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Date accepted:30 May 2022
Date deposited:08 July 2022
Date of first online publication:30 June 2022
Date first made open access:08 July 2022

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