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Solid‐State Emission from Mono‐ and Bichromophoric Boron Dipyrromethene (BODIPY) Derivatives and Comparison with Fluid Solution

Lookup NU author(s): Dr Ozgur Bozdemir, Hatun AlSharif, Emeritus Professor William McFarlane, Dr Paul Waddell, Professor Andrew Benniston, Emeritus Professor Anthony Harriman

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This is the authors' accepted manuscript of an article that has been published in its final definitive form by Wiley -VCH Verlag GmbH & Co. KGaA, 2019.

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Abstract

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimThe syntheses and crystal structures of sterically crowded mono- and bichromophoric BODIPY-based dyes are reported. The “monomeric” compound is weakly fluorescent in the liquid phase due to fast internal conversion associated with rotation of aryl rings at the boron atom. The side-by-side “dimer” exhibits weak excitonic coupling between the dipyrrin units and is much more emissive in fluid solution. Solid samples of both molecular entities are strongly fluorescent under near-UV illumination. Thus, the mono-chromophore exhibits dual fluorescence from what appears to be a mixture of crystalline and possibly amorphous (or interfacial regions) distributions. The bi-chromophore packs in the crystal as pairs of chromophores with each unit being provided by a different molecule. This leads to excitonic splitting and the formation of a strong H-band in the absorption spectrum. Fluorescence occurs from the corresponding J-species and also from what appears to be an aggregated state associated with interfacial areas. Both bulk and interface-bound states show relatively long-lived fluorescence while the crystal structures indicate the likelihood for fast electronic energy migration between molecules.

Publication metadata

Author(s): Bozdemir OA, Al-Sharif HHT, McFarlane W, Waddell PG, Benniston AC, Harriman A

Publication type: Article

Publication status: Published

Journal: Chemistry - A European Journal

Year: 2019

Volume: 25

Issue: 68

Pages: 15634-15645

Print publication date: 05/12/2019

Online publication date: 04/10/2019

Acceptance date: 04/10/2019

Date deposited: 03/12/2019

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: Wiley -VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/chem.201903902

DOI: 10.1002/chem.201903902

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