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Synlett 2022; 33(14): 1357-1362
DOI: 10.1055/a-1806-5999
DOI: 10.1055/a-1806-5999
cluster
Organic Chemistry in Thailand
Pillar[4]arene[1]thioarenes: Synthesis and Host–Guest Binding Properties
This research project is supported by Mahidol University (Basic Research Fund: fiscal year 2021) and the Mid-Career Researcher Development grant (NRCT5-RSA63015-22) jointly funded by the National Research Council of Thailand and Mahidol University.
Abstract
The synthesis and characterization of a novel class of pillar[4]arene[1]thioarenes (P[4]A[1]SMe) are reported. An oxidation–thionation strategy was used to replace a single dialkoxybenzene panel in the parent pillar[5]arene. 1H NMR spectroscopic titration experiments, supported by density functional theory computational studies, revealed that P[4]A[1]SMe show starkly modulated host–guest binding properties for electron-deficient aliphatic guests.
Key words
sulfurization - Lawesson’s reagent - pillar[4]arene[1]thioquinone - pillar[4]arene[1]thioarenes - host–guest complex - supramolecular chemistrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1806-5999.
- Supporting Information
- CIF File
Publication History
Received: 13 February 2022
Accepted after revision: 23 March 2022
Accepted Manuscript online:
23 March 2022
Article published online:
28 April 2022
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References and Notes
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