Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality. Issue 16 (4th April 2023)

• Record Type: Journal Article
• Authors: He, Jing; Yu, Mo-Han; Lian, Zhe; Fan, Yan-Qing; Guo, Sheng-Zhu; Li, Xiao-Nan; Wang, Ying; Wang, Wen-Guang; Cheng, Zhi-Yun; Jiang, Hua
• Is Part Of: Chemical science. Volume 14:Issue 16(2023)
• Page Start: 4426
• Page End: 4433
• Publication Date: 2023-04-04
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc06825g
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We report herein two lemniscular carbon nanohoops bis-po -CC and bis-pm -TC with contiguous conjugation from planar chiral [2.2]paracyclophane, and elucidate the influence of the regioselective synthesis on their topological chirality. Abstract : We report herein the regioselective synthesis of all-carbon lemniscular nanohoops bis-po -CC and bis-pm -TC by the rational control of ring closures at the different positions of planar chiral tetrasubstituted [2.2]paracyclophane. Topological analyses reveal that bis-pm -TC is topologically chiral while bis-po -CC is topologically achiral. X-ray crystal analysis demonstrates that bis-pm -TC adopts a lemniscular conformation with a contiguous conjugation. CD and CPL measurements further reveal that the chiroptical properties of bis-pm -TC are obviously different from those of bis-po -CC due to their different topological chiralities.