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

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

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 s...

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Veröffentlicht in:Journal of organic chemistry 2021-09, Vol.86 (18), p.13100-13103
Hauptverfasser: Rösch, Andreas T, Söntjens, Serge H. M, Robben, Jorn, Palmans, Anja R. A, Schnitzer, Tobias
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container_end_page 13103
container_issue 18
container_start_page 13100
container_title Journal of organic chemistry
container_volume 86
creator Rösch, Andreas T
Söntjens, Serge H. M
Robben, Jorn
Palmans, Anja R. A
Schnitzer, Tobias
description 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.
doi_str_mv 10.1021/acs.joc.1c00922
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title Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study
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