Cited by 66Supramolecular Chemistry and ComplexesLuminescence and Fluorescent MaterialsSupramolecular Self-Assembly in Materials

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

Yu, Yang, Li, Yawen, Wang, Xiaoqing, Nian, Hao, Wang, Le, Li, Jie, Zhao, Yanxia, Yang, Xiran +2 more·2017·The Journal of Organic Chemistry

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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Crossref · 10.1021/acs.joc.7b00400

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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
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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