Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 11, Pages 5590-5596Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00400
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Funding
- National Natural Science Foundation of China [21472149, 21472143]
- Shaanxi Provincial Natural Science Foundation [2016JM2025, 2016JQ2015]
- Research Project of Shaanxi Provincial Education Department [15Js112]
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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 center dot center dot center dot 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 degrees 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.
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