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

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.