Cucurbit[10]uril-Based [2]Rotaxane: Preparation and Supramolecular Assembly-Induced Fluorescence Enhancement

5 years ago

Cucurbit[10]uril-Based [2]Rotaxane: Preparation and Supramolecular Assembly-Induced Fluorescence Enhancement

Le Wang, Liping Cao, Yang Yu, Yawen Li, Xiaoqing Wang, Yanxia Zhao, Simin Liu, Jie Li, Xiran Yang, Hao Nian

As the cucurbit[n]uril (CB[n]) homologue with the largest cavity size, cucurbit[10]uril (CB[10]) can encapsulate big guests to form interesting host–guest complexes/assemblies. Herein, we report the preparation and fluorescence properties of CB[10]-based [2]rotaxane (CB[10]·1) formed from cucurbit[10]uril and dumbbell-like guest 1. This [2]rotaxane (CB[10]·1) is assembled by C═O···N⁺ ion–dipole interactions between oxygen atoms of the carbonyl fringed portals of CB[10] and the positively charged pyridinium units of 1 via the slipping method under heating at 95 °C in DMSO. In contrast, other cucurbit[n]uril (CB[n], n = 6–8) homologues cannot form rotaxanes with 1 due to their smaller cavities. The dumbbell-like guest 1 is a poor emitter in DMSO. Interestingly, the formation of CB[10]·1 renders the restriction of intramolecular rotation of TPE, which features a strong fluorescent intensity, long lifetime, and high quantum yield. Furthermore, CB[10]·1 is shown to aggregate plate-like structures with various sizes in different solvents (DMSO, THF, or CHCl₃), resulting in a stepwise aggregation-induced emission enhancement effect. This kind of CB[10]-based [2]rotaxane may be used to fabricate luminescent systems with unique emission properties.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00400

DOI: 10.1021/acs.joc.7b00400