Cyclobis[2,5-(thiophenedimethane)-4,4'-(triphenylamine)] versus Its S, S-Dioxidized Macrocycle: Global Antiaromaticity and Intramolecular Dynamics

Fernando Lopez-Garcia; Shaoqiang Dong; Yi Han; Johnathan Joo Cheng Lee; Pei Wen Ng; Chunyan Chi

doi:10.1021/acs.orglett.1c02200

Cyclobis[2,5-(thiophenedimethane)-4,4'-(triphenylamine)] versus Its S, S-Dioxidized Macrocycle: Global Antiaromaticity and Intramolecular Dynamics

Org Lett. 2021 Aug 20;23(16):6382-6386. doi: 10.1021/acs.orglett.1c02200. Epub 2021 Jul 30.

Authors

Fernando Lopez-Garcia¹, Shaoqiang Dong¹, Yi Han¹, Johnathan Joo Cheng Lee¹, Pei Wen Ng¹, Chunyan Chi¹

Affiliation

¹ Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543.

PMID: 34328336
DOI: 10.1021/acs.orglett.1c02200

Abstract

Fully conjugated macrocycles containing benzenoid rings rarely show global aromaticity/antiaromaticity. Herein, we report an annulene-like macrocycle CBTT and its S,S-dioxidized macrocycle DOCBTT with alternative quinoidal thiophene/1,1-dioxide thiophene and triphenyl amine moieties. They both showed temperature-dependent intramolecular dynamics and global antiaromatic character with 32π electrons at low temperature. However, CBTT and DOCBTT have different conjugated pathways.