We demonstrate a new synthetic strategy to cyclophanes containing thiophene and indole moieties via Grignard addition, Fischer indolization and ring-closing metathesis as key steps.
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http://dx.doi.org/10.3762/bjoc.11.165 | DOI Listing |
Angew Chem Int Ed Engl
October 2024
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Org Biomol Chem
July 2021
Division of Applied Chemistry, Faculty of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji, Tokyo 192-0397, Japan.
Intramolecular charge transfer (ICT) fluorescence has been widely investigated and exploited in sensor molecules. However, steric effects on the ICT fluorescence properties have rarely been reported so far, although research in this area would promote an understanding of the basics of solvation. Herein, we report the detailed fluorescence properties of bis(trimethylsilyl)benzo[b]thiophene-1,1-dioxide (TMSBTO2) and its caged cyclophanes and non-cage isomers, which demonstrate ICT fluorescence in various solutions.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
February 2020
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore.
We report the template-free synthesis and characterization of a new type of porphyrin/quinoidal-bithiophene-based conjugated macrocycle. X-ray crystallographic analysis of the dimer (2MC) revealed a cyclophane-like geometry with large dihedral angles between the porphyrin and the neighboring thiophene rings, and NMR measurements and theoretical calculations confirmed a localized aromatic character of the porphyrin/thiophene rings and quinoidal character of the bithiophene linkers. Restricted rotation of the thiophene rings linked to the porphyrin unit was observed by variable-temperature NMR measurements.
View Article and Find Full Text PDFBeilstein J Org Chem
October 2015
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai-400 076, India.
We demonstrate a new synthetic strategy to cyclophanes containing thiophene and indole moieties via Grignard addition, Fischer indolization and ring-closing metathesis as key steps.
View Article and Find Full Text PDFJ Am Chem Soc
July 2009
Functional Modules Group, Organic Nanomaterials Center, National Institute for Materials Science, Ibaraki, Japan.
The polythiophene polyrotaxane was synthesized through electrochemical polymerization of the [2]rotaxane consisting of the electron-rich dumbbell-shaped sexithiophene and the electron-deficient cyclophane of cyclobis(paraquat-p-phenylene). The optical and electrochemical property of the polythiophene polyrotaxane film was characterized. The material reported herein is attractive not only as a component for constructing the macromolecular machine but also as a new type of insulated molecular wire having donor-acceptor interaction between the macrocycle and the conductive polymer.
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