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Supramolecular Polymeric Radicals: Highly Promoted Formation and Stabilization of Naphthalenediimide Radical Anions.

Authors
  • Yang, Yuchong1
  • Hu, Hao1
  • Guo, Yuanyuan2
  • Xia, Andong2
  • Xu, Jiang-Fei1
  • Zhang, Xi1, 3
  • 1 Key Lab of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing, 100084, China. , (China)
  • 2 The Key Laboratory of Photochemistry, Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. , (China)
  • 3 State Key Lab of Supramolecular Structure and Materials, Jilin University, Changchun, 130012, China. , (China)
Type
Published Article
Journal
Macromolecular rapid communications
Publication Date
Dec 01, 2020
Volume
41
Issue
24
Identifiers
DOI: 10.1002/marc.202000080
PMID: 32419213
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The supramolecular polymeric radicals are developed to promote the generation efficiency and stability of naphthalenediimide (NDI) radical anions. To this end, a water-soluble bifunctional monomer bearing two naphthalene-viologen end groups and a NDI center is designed and synthesized. The supramolecular polymeric NDI radical anions are fabricated on the basis of host-guest complexation between the NDI-containing bifunctional monomer and cucurbit[8]uril (CB[8]) and followed by the photoinduced electron transfer process under UV light irradiation. The electrostatic effect of CB[8] and the bulky and rigid structure of supramolecular polymer are combined to stabilize the excited state of NDIs and NDI radical anions, contributing to the high enhancement of the formation of NDI radical anions with excellent stability. It is found that the highest occupied molecular orbital energy and lowest unoccupied molecular orbital energy of NDI are also lowered by the formation of supramolecular polymer. In addition, the supramolecular polymeric NDI radical anions could be utilized as a supramolecular photoreducing agent to reduce cytochrome C with a higher efficiency. It is anticipated that other radicals can also be stabilized through this strategy, and this line of research may lead to the development of novel polymeric radical materials. © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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