Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study

[Image: see text] The conformational analysis of a 2,4-bis(4-dialkylamino-2-amido)phenyl squaraine dye revealed the presence of two rotational isomers at room temperature. Combination of spectroscopic and computational techniques showed that the rotational barrier is influenced by hydrogen bonds bet...

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Autores principales: Rösch, Andreas T., Söntjens, Serge H. M., Robben, Jorn, Palmans, Anja R. A., Schnitzer, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453623/
https://www.ncbi.nlm.nih.gov/pubmed/34469161
http://dx.doi.org/10.1021/acs.joc.1c00922
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author Rösch, Andreas T.
Söntjens, Serge H. M.
Robben, Jorn
Palmans, Anja R. A.
Schnitzer, Tobias
author_facet Rösch, Andreas T.
Söntjens, Serge H. M.
Robben, Jorn
Palmans, Anja R. A.
Schnitzer, Tobias
author_sort Rösch, Andreas T.
collection PubMed
description [Image: see text] The conformational analysis of a 2,4-bis(4-dialkylamino-2-amido)phenyl squaraine dye revealed the presence of two rotational isomers at room temperature. Combination of spectroscopic and computational techniques showed that the rotational barrier is influenced by hydrogen bonds between the amido substituents and the oxygen atoms at the quadratic core. Even small amounts of trifluoroacetic acid interfered with the intramolecular hydrogen bond formation and accelerated the interconversion of the conformers.
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spelling pubmed-84536232021-09-22 Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study Rösch, Andreas T. Söntjens, Serge H. M. Robben, Jorn Palmans, Anja R. A. Schnitzer, Tobias J Org Chem [Image: see text] The conformational analysis of a 2,4-bis(4-dialkylamino-2-amido)phenyl squaraine dye revealed the presence of two rotational isomers at room temperature. Combination of spectroscopic and computational techniques showed that the rotational barrier is influenced by hydrogen bonds between the amido substituents and the oxygen atoms at the quadratic core. Even small amounts of trifluoroacetic acid interfered with the intramolecular hydrogen bond formation and accelerated the interconversion of the conformers. American Chemical Society 2021-09-01 2021-09-17 /pmc/articles/PMC8453623/ /pubmed/34469161 http://dx.doi.org/10.1021/acs.joc.1c00922 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Rösch, Andreas T.
Söntjens, Serge H. M.
Robben, Jorn
Palmans, Anja R. A.
Schnitzer, Tobias
Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study
title Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study
title_full Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study
title_fullStr Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study
title_full_unstemmed Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study
title_short Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study
title_sort rotational isomerism of an amide substituted squaraine dye: a combined spectroscopic and computational study
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453623/
https://www.ncbi.nlm.nih.gov/pubmed/34469161
http://dx.doi.org/10.1021/acs.joc.1c00922
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