Cucurbit[10]uril-Based [2]Rotaxane: Preparation and Supramolecular Assembly-Induced Fluorescence Enhancement
Abstract
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 CHCl 3 ), 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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- Authors
- Yu, Y., Li, Y., Wang, X., Nian, H., Wang, L., Li, J., Zhao, Y., Yang, X., Liu, S., & Cao, L.
- Affiliations
- Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi’an, 710069, P. R. China
- Northwest University (CN)
- Wuhan University of Science and Technology (CN)
- Corresponding author
- Liu, Simin
- Cao, Liping
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-05-19
- Volume
- 82
- Issue
- 11
- Pages
- 5590-5596
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2613470686
- Cited by
- 66
- References
- 85
- Citations by year
- 2026: 2 · 2025: 4 · 2024: 8 · 2023: 6 · 2022: 8 · 2021: 9 · 2020: 8 · 2019: 8 · 2018: 8 · 2017: 5
- FWCI
- 3.32
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Organic Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Natural Science Foundation of China (21472143, 21472149)
- Natural Science Foundation of Shaanxi Province (2016JM2025, 2016JQ2015)
- Education Department of Shaanxi Province (15Js112)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Supramolecular Chemistry and Complexes
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
- Keywords
- [2]rotaxanes, supramolecular self-assembly, fluorescence enhancement, aggregation-induced emission, host-guest complexation, ion-dipole interactions, supramolecular aggregation
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