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

J Org Chem

Laboratory of Macromolecular and Organic Chemistry, and Institute for Complex Molecular Systems, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands.

Published: September 2021

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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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453623PMC
http://dx.doi.org/10.1021/acs.joc.1c00922DOI Listing

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