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Synthesis, Structure and Photophysical Properties of a New Class of Inherently Chiral Boron(III) Chelates—The tert-Leucine Complexes

Lookup NU author(s): Nawaf Algoazy, Dr Julian Knight, Dr Paul Waddell, Dr Joshua Karlsson, Emeritus Professor Anthony Harriman

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Abstract

© 2020 Wiley-VCH GmbH. A new family of boron(III) chelates is introduced whereby molecular chirality, confirmed by circular dichroism, is imported during synthesis such that isolation of the diastereoisomers does not require separation procedures. The photophysical properties of two members of the family have been examined: the N,O,O-salicylaldehyde-based derivative shows pronounced intramolecular charge-transfer character in fluid solution and is weakly fluorescent, with a large Stokes shift. The corresponding 2-methylamino-benzaldehyde-derived N,N,O-chelate absorbs and fluoresces in the visible region with a much smaller Stokes shift. Orange fluorescence is also observed for this compound as a cast film. Temperature-dependence studies show that decay of the fluorescent state is weakly activated but emission is less than quantitative at 77 K. Quite rare for boron(III)-based chelates, this derivative undergoes intersystem crossing to form a meta-stable triplet-excited state. X-ray crystal structures are reported for both compounds, along with simulated ECD spectra.


Publication metadata

Author(s): Algoazy N, Knight JG, Waddell PG, Aerts R, Herrebout W, Al-Sharif HHT, Karlsson JKG, Harriman A

Publication type: Article

Publication status: Published

Journal: Chemistry: A European Journal

Year: 2021

Volume: 27

Issue: 16

Pages: 5246-5258

Print publication date: 17/03/2021

Online publication date: 28/12/2020

Acceptance date: 28/12/2020

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: Wiley-VCH Verlag

URL: https://doi.org/10.1002/chem.202005246

DOI: 10.1002/chem.202005246


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