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Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid

Solutions of 5‐N‐arylaminothiazoles containing pyridyl groups exhibited clear halochromism and halofluorism upon addition of Brønsted and Lewis acids. The addition of triflic acid to solutions of 5‐N‐arylaminothiazoles in Et(2)O induced bathochromic shifts of the absorption and emission bands. DFT c...

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Autores principales: Yamaguchi, Kirara, Murai, Toshiaki, Guo, Jing‐Dong, Sasamori, Takahiro, Tokitoh, Norihiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5062007/
https://www.ncbi.nlm.nih.gov/pubmed/27777834
http://dx.doi.org/10.1002/open.201600059
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author Yamaguchi, Kirara
Murai, Toshiaki
Guo, Jing‐Dong
Sasamori, Takahiro
Tokitoh, Norihiro
author_facet Yamaguchi, Kirara
Murai, Toshiaki
Guo, Jing‐Dong
Sasamori, Takahiro
Tokitoh, Norihiro
author_sort Yamaguchi, Kirara
collection PubMed
description Solutions of 5‐N‐arylaminothiazoles containing pyridyl groups exhibited clear halochromism and halofluorism upon addition of Brønsted and Lewis acids. The addition of triflic acid to solutions of 5‐N‐arylaminothiazoles in Et(2)O induced bathochromic shifts of the absorption and emission bands. DFT calculations suggested that the spectral changes arise from the protonation of the pyridyl group of the thiazoles in Et(2)O. Single‐crystal X‐ray diffraction analysis of a thiazole and its protonated form revealed the change of the conformation around the thiazole ring. The emission of white light was accomplished from a single fluorescent dye by adjusting the ratio of dye and B(C(6)F(5))(3), whereby the International Commission on Illumination coordinates showed a linear change from blue to orange.
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spelling pubmed-50620072016-10-24 Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid Yamaguchi, Kirara Murai, Toshiaki Guo, Jing‐Dong Sasamori, Takahiro Tokitoh, Norihiro ChemistryOpen Communications Solutions of 5‐N‐arylaminothiazoles containing pyridyl groups exhibited clear halochromism and halofluorism upon addition of Brønsted and Lewis acids. The addition of triflic acid to solutions of 5‐N‐arylaminothiazoles in Et(2)O induced bathochromic shifts of the absorption and emission bands. DFT calculations suggested that the spectral changes arise from the protonation of the pyridyl group of the thiazoles in Et(2)O. Single‐crystal X‐ray diffraction analysis of a thiazole and its protonated form revealed the change of the conformation around the thiazole ring. The emission of white light was accomplished from a single fluorescent dye by adjusting the ratio of dye and B(C(6)F(5))(3), whereby the International Commission on Illumination coordinates showed a linear change from blue to orange. John Wiley and Sons Inc. 2016-08-02 /pmc/articles/PMC5062007/ /pubmed/27777834 http://dx.doi.org/10.1002/open.201600059 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Yamaguchi, Kirara
Murai, Toshiaki
Guo, Jing‐Dong
Sasamori, Takahiro
Tokitoh, Norihiro
Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid
title Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid
title_full Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid
title_fullStr Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid
title_full_unstemmed Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid
title_short Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid
title_sort acid‐responsive absorption and emission of 5‐n‐arylaminothiazoles: emission of white light from a single fluorescent dye and a lewis acid
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5062007/
https://www.ncbi.nlm.nih.gov/pubmed/27777834
http://dx.doi.org/10.1002/open.201600059
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