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)

Research output: Contribution to journalArticleAcademicpeer-review

5 Downloads (Pure)

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 languageEnglish
Pages (from-to)13100-13103
Number of pages4
JournalJournal of Organic Chemistry
Volume86
Issue number18
DOIs
Publication statusPublished - 17 Sep 2021

Bibliographical note

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

Fingerprint

Dive into the research topics of 'Rotational Isomerism of an Amide Substituted Squaraine Dye: A Combined Spectroscopic and Computational Study'. Together they form a unique fingerprint.

Cite this