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Modulation of the Naked-Eye and Fluorescence Color of a Protonated Boron-Doped Thiazolothiazole by Anion-Dependent Hydrogen Bonding

Hagspiel, Stephan, Fantuzzi, Felipe, Arrowsmith, Merle, Gärtner, Annalena, Fest, Maximilian, Weiser, Jonas, Engels, Bernd, Helten, Holger, Braunschweig, Holger (2022) Modulation of the Naked-Eye and Fluorescence Color of a Protonated Boron-Doped Thiazolothiazole by Anion-Dependent Hydrogen Bonding. Chemistry - A European Journal, 28 (49). Article Number e20220139. ISSN 0947-6539. E-ISSN 1521-3765. (doi:10.1002/chem.202201398) (KAR id:98587)

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Official URL:
https://doi.org/10.1002/chem.202201398

Abstract

The reaction of a cyclic alkyl(amino)carbene (CAAC)-stabilized thiazaborolo[5,4-d]thiazaborole (TzbTzb) with strong Brønsted acids, such as HCl, HOTf (Tf=O2SCF3) and [H(OEt2)2][BArF4] (ArF=3,5-(CF3)2C6H3), results in the protonation of both TzbTzb nitrogen atoms. In each case X-ray crystallographic data show coordination of the counteranions (Cl−, OTf−, BArF4−) or solvent molecules (OEt2) to the doubly protonated fused heterocycle via hydrogen-bonding interactions, the strength of which strongly influences the 1H NMR shift of the NH protons, enabling tuning of both the visible (yellow to red) and fluorescence (green to red) colors of these salts. DFT calculations reveal that the hydrogen bonding of the counteranion or solvent to the protonated nitrogen centers affects the intramolecular TzbTzb-to-CAAC charge transfer character involved in the S0→S1 transition, ultimately enabling fine-tuning of their absorption and emission spectral features.

Item Type: Article
DOI/Identification number: 10.1002/chem.202201398
Subjects: Q Science > QD Chemistry
Divisions: Divisions > Division of Natural Sciences > Chemistry and Forensics
Funders: Deutsche Forschungsgemeinschaft (https://ror.org/018mejw64)
Coordenação de Aperfeicoamento de Pessoal de Nível Superior (https://ror.org/00x0ma614)
Alexander von Humboldt Foundation (https://ror.org/012kf4317)
Depositing User: Felipe Fantuzzi
Date Deposited: 01 Dec 2022 01:10 UTC
Last Modified: 02 Dec 2022 09:35 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/98587 (The current URI for this page, for reference purposes)
Hagspiel, Stephan: https://orcid.org/0000-0002-6049-6007
Fantuzzi, Felipe: https://orcid.org/0000-0002-8200-8262
Arrowsmith, Merle: https://orcid.org/0000-0003-1449-5932
Weiser, Jonas: https://orcid.org/0000-0001-6698-2519
Engels, Bernd: https://orcid.org/0000-0003-3057-389X
Helten, Holger: https://orcid.org/0000-0003-1273-3685
Braunschweig, Holger: https://orcid.org/0000-0001-9264-1726
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