Pillar[4]arene[1]thioarenes: Synthesis and Host–Guest Binding Properties

Adisorn Khanthong; Korawit Khamphaijun; Araya Ruengsuk; Andrew Docker; Taweetham Limpanuparb; Jonggol Tantirungrotechai; Thanthapatra Bunchuay

doi:10.1055/a-1806-5999

Synlett, Table of Contents

Synlett 2022; 33(14): 1357-1362
DOI: 10.1055/a-1806-5999

cluster

Organic Chemistry in Thailand

Pillar[4]arene[1]thioarenes: Synthesis and Host–Guest Binding Properties

Authors

Adisorn Khanthong

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, 10400, Thailand
Korawit Khamphaijun

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, 10400, Thailand
Araya Ruengsuk

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, 10400, Thailand
Andrew Docker

^bDepartment of Chemistry, University of Oxford Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
Taweetham Limpanuparb ∗

^cScience Division, Mahidol University International College, Mahidol University, Salaya, 73170, Thailand
Jonggol Tantirungrotechai

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, 10400, Thailand
Thanthapatra Bunchuay ∗

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok, 10400, Thailand

Abstract

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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 chemistry

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References

References and Notes

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