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Synthesis, Stereochemical and Photophysical Properties of Functionalized Thiahelicenes

Authors :
Cauteruccio, Valentina Pelliccioli
Francesca Cardano
Giacomo Renno
Francesca Vasile
Claudia Graiff
Giuseppe Mazzeo
Andrea Fin
Giovanna Longhi
Sergio Abbate
Alessia Rosetti
Claudio Villani
Guido Viscardi
Emanuela Licandro
Silvia
Source :
Catalysts; Volume 12; Issue 4; Pages: 366
Publication Year :
2022
Publisher :
Multidisciplinary Digital Publishing Institute, 2022.

Abstract

We report on the synthesis of a novel class of functionalized thia[6]helicenes and a thia[5]helicene, containing a benzothiophene unit and a second heteroatom embedded in the helix (i.e., nitrogen and oxygen) or a pyrene or a spirobifluorene moiety. These systems are obtained through straightforward and general procedures that involve: (i) palladium-catalyzed annulation of iodo-atropoisomers with internal alkynes and (ii) Suzuki coupling of iodo-atropoisomers with phenyl boronic acid followed by a Mallory-type reaction. Both experimental and theoretical studies on the configurational stability of some selected thia[6]helicenes confirmed their stability toward racemization at room temperature, while the pyrene-based thia[5]helicene was found to be unstable. Moreover, the configuration assignment for one representative thiahelicene was established through the comparison between experimental and theoretical circular dichroism (CD) spectra. A systematic study of the photophysical properties of both thiahelicenes and the corresponding atropoisomers has been carried out to provide a complete overview on the new molecules proposed in this work. The obtained data showed regular trends in all the thiahelicene series with spectroscopic traits in line with those previously observed for similar heterohelicenes.

Details

Language :
English
ISSN :
20734344
Database :
OpenAIRE
Journal :
Catalysts; Volume 12; Issue 4; Pages: 366
Accession number :
edsair.multidiscipl..3157e61c57fa1ecd8e6ac7e3d71348f6
Full Text :
https://doi.org/10.3390/catal12040366