Geminiarene: Molecular Scale Dual Selectivity for Chlorobenzene and Chlorocyclohexane Fractionation

• Published in: Journal of the American Chemical Society Vol. 141; no. 31; pp. 12280 - 12287
• Main Authors: Wu, Jia-Rui, Yang, Ying-Wei
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 07.08.2019
• Subjects: chemistry; chlorobenzene; fractionation
• ISSN: 0002-7863; 1520-5126; 1520-5126
• DOI: 10.1021/jacs.9b03559

In this work, a new version of macrocyclic arenes, namely geminiarene, has been designed and synthesized for guest complexation and chlorobenzene/chlorocyclohexane mixture separation with excellent dual selectivity. Due to its unique dual/gemini conformational feature, not only chlorocyclohexane can be separated from chlorobenzene with exceeding 97% purity but also chlorobenzene can be separated from chlorocyclohexane with purity over 88%, and the dual selective fractionation process could be achieved in only one cycle of operation. Significantly, we demonstrate that the dual selectivity capability is essentially a competition of the stability between the guest-free and guest-loaded crystalline phases of geminiarene. We strongly believe that this work and the idea of multiple selective separation systems will open up new perspectives on macrocycle-based solid-state host–guest chemistry and molecular scale separation materials.