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Bay-Substituted Thiaza[5]helicenes: Synthesis and Implications on Structural and Spectroscopic Properties

Journal Contribution - Journal Article

A series of bay-substituted thiaza[5]helicenes was synthesized to investigate the effect of different substituents on the properties of these helicenes. These thiaza[5]helicenes with different substituents were prepared in a straightforward manner through indole- and benzo[b]thiophene synthesis, palladium-catalyzed Suzuki coupling, oxidative cyclization, and functional group interconversion reactions. We investigated the impact of these different bay area substituents compared to the unsubstituted thiaza[5]helicene on the structural parameters and studied the steady-state electronic spectroscopy of these thiaza[5]helicenes in toluene and acetonitrile. We found that different functional groups influence the solid state structure and spectroscopic properties, but a single substituent in the bay area of a thiaza[5]helicene was not enough to prevent enantiomerization at room temperature.
Journal: Journal of Organic Chemistry
ISSN: 0022-3263
Issue: 21
Volume: 84
Pages: 13528 - 13539
Publication year:2019
BOF-keylabel:yes
IOF-keylabel:yes
BOF-publication weight:2
CSS-citation score:1
Authors from:Higher Education
Accessibility:Open