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

Andreas T. Rösch; Serge H.M. Söntjens; Jorn Robben; Anja R.A. Palmans; Tobias Schnitzer

doi:10.1021/acs.joc.1c00922

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

Andreas T. Rösch, Serge H.M. Söntjens, Jorn Robben, Anja R.A. Palmans, Tobias Schnitzer (Corresponding author)

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Abstract

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.

Original language	English
Pages (from-to)	13100-13103
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	86
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.1c00922
Publication status	Published - 17 Sept 2021

Bibliographical note

Publisher Copyright:
© 2021 The Authors. Published by American Chemical Society.

Funding

The authors acknowledge funding from the Dutch Ministry of Education, Culture and Science (Gravity program 24.001.035). T.S. thanks the Swiss National Science Foundation for a Postdoc.Mobility fellowship.

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10.1021/acs.joc.1c00922

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AU - Robben, Jorn

AU - Palmans, Anja R.A.

AU - Schnitzer, Tobias

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

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