Control of the thermal cis to trans isomerizations of azobenzene and thioindigo derivatives by the formation of supramolecular H‐bonded assemblies

Jacqueline Rosengaus, Itamar Willner*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

2,3‐Bis(aminocyclohexyl)−6‐methoxy‐1,3,5‐triazine (1a) forms intermolecular H‐bonded complexes with 3,3′‐diacetyl‐cis‐azoenzene (4) and 6,6′‐diethoxy‐cis‐thioindigo (5b), (association constants K = 4.9 × 104 and 3.5 × 105 1 mol−1, respectively). The thermal cis→trans isomerization of 4b and 5b to 3,3′‐diacetyl‐trans‐azobenzene (4a), and 6,6′‐diethoxy‐trans‐thioindigo (5a), is inhibited in the intermolecular complex 1a–4b and 1a–5b. Molecular mechanics calculations support the formation of the intermolecular H‐bonded complexes between 1a and 4b or 5b.

Original languageEnglish
Pages (from-to)54-62
Number of pages9
JournalJournal of Physical Organic Chemistry
Volume8
Issue number1
DOIs
StatePublished - Jan 1995

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