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Solvent-Driven Conformational Exchange for Amide-Linked Bichromophoric BODIPY Derivatives

Lookup NU author(s): Patrycja Stachelek, Dr Sanatan Chattopadhyay, Emeritus Professor Anthony Harriman



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, 2016.

For re-use rights please refer to the publisher's terms and conditions.


The fluorescence lifetime and quantum yield are seen to depend in an unexpected manner on the nature of the solvent for a pair of tripartite molecules composed of two identical boron dipyrromethene (BODIPY) residues attached to a 1,10-phenanthroline core. A key feature of these molecular architectures concerns the presence of an amide linkage that connects the BODIPY dye to the heterocyclic platform. The secondary amide derivative is more sensitive to environmental change than is the corresponding tertiary amide. In general, increasing solvent polarity, as measured by the static dielectric constant, above a critical threshold tends to reduce fluorescence but certain hydrogen bond accepting solvents exhibit anomolous behaviour. Fluorescence quenching is believed to arise from light-induced charge transfer between the two BODIPY dyes, but thermodynamic arguments alone do not explain the experimental findings. Molecular modelling is used to argue that the conformation changes in strongly polar media in such a way as to facilitate improved rates of light-induced charge transfer. These solvent-induced changes, however, differ remarkably for the two types of amide.

Publication metadata

Author(s): Thakare S, Stachelek P, Mula S, More AB, Chattopadhyay S, Ray AK, Sekar N, Ziessel R, Harriman A

Publication type: Article

Publication status: Published

Journal: Chemistry: A European Journal

Year: 2016

Volume: 22

Issue: 40

Pages: 14356-14366

Print publication date: 26/09/2016

Online publication date: 16/08/2016

Acceptance date: 01/08/2016

Date deposited: 13/09/2016

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA


DOI: 10.1002/chem.201602354


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