ArticleThe Journal of organic chemistry2021
Exploring the Photocyclization Pathways of Styrylthiophenes in the Synthesis of Thiahelicenes: When the Theory and Experiment Meet.
Article in The Journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Transformation of Silyl-Protected Tetrafluorinated Thia[6]helicene S-Oxide into a Difluorinated Coronene via Induced Desilylation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Design and synthesis of thiahelicenes for molecular electronics.Frontiers in chemistry · 2024Article
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Authors and funding
3 authors.
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Abstract
The introduction of thiophene rings to the helical structure of carbohelicenes has electronic effects that may be used advantageously in organic electronics. The performance of these devices is highly dependent on the sulfur atom topology, so a precise knowledge of the synthetic routes that may afford isomeric structures is necessary. We have studied the photocyclization pathway of both 2- and 3-styrylthiophenes on their way to thiahelicenes by experiment and theory. To begin with, the synthesis of stereochemically well-defined 2- and 3-styrylthiophenes allowed us to register first, and simulate later, the UV-vis electronic spectra of these precursors. This information gave us access through time-dependent density functional theory calculations to the very nature of the excited states involved in the photocyclization step and from there to the regio- and stereochemical outcome of the reaction. For the widely known case of a 2-styrylthiophene derivative, the expected naphtho[2,1-
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