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Cycloparaphenylene Double Nanohoop: Structure, Lamellar Packing, and Encapsulation of C60 in the Solid State


Yang, Yong; Huangfu, Shangxiong; Sato, Sota; Juricek, Michal (2021). Cycloparaphenylene Double Nanohoop: Structure, Lamellar Packing, and Encapsulation of C60 in the Solid State. Organic Letters, 23(20):7943-7948.

Abstract

A new member of the cycloparaphenylene double-nanohoop family was synthesized. Its π-framework features two oval cavities that display different shapes depending on the crystallization conditions. Incorporation of the peropyrene bridge within the nanoring cycles via bay-regions alleviates steric effects and thus allows 1:1 complexation with C60 in the solid state. This nanocarbon adopts a lamellar packing motif, and our results suggest that the structural adjustment of this double nanohoop could enable its use in supramolecular and semiconductive materials.

Abstract

A new member of the cycloparaphenylene double-nanohoop family was synthesized. Its π-framework features two oval cavities that display different shapes depending on the crystallization conditions. Incorporation of the peropyrene bridge within the nanoring cycles via bay-regions alleviates steric effects and thus allows 1:1 complexation with C60 in the solid state. This nanocarbon adopts a lamellar packing motif, and our results suggest that the structural adjustment of this double nanohoop could enable its use in supramolecular and semiconductive materials.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry, Physical and Theoretical Chemistry, Biochemistry
Language:English
Date:15 October 2021
Deposited On:15 Feb 2022 14:08
Last Modified:26 Jun 2024 01:53
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Hybrid
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1021/acs.orglett.1c02950
Project Information:
  • : FunderSNSF
  • : Grant IDPP00P2_170534
  • : Project TitleControl of Spin Interactions in Helical Systems
  • : FunderSNSF
  • : Grant IDPP00P2_198900
  • : Project TitleA â��Closer Lookâ�� at Open-Shell Nanographenes Through Bond and Space
  • : FunderH2020
  • : Grant ID716139
  • : Project TitleINSPIRAL - Spin-Delocalization with a Twist: Chiral Open-Shell Helices
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)