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      Structural deformation and host–guest properties of doubly-reduced cycloparaphenylenes, [ n]CPPs 2− ( n = 6, 8, 10, and 12)†

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      Chemical Science
      The Royal Society of Chemistry

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          Abstract

          Chemical reduction of several cycloparaphenylenes (CPPs) ranging in size from [8]CPP to [12]CPP has been investigated with potassium metal in THF. The X-ray diffraction characterization of the resulting doubly-reduced [ n]CPPs provided a unique series of carbon nanohoops with increasing dimensions and core flexibility for the first comprehensive structural analysis. The consequences of electron acquisition by a [ n]CPP core have been analyzed in comparison with the neutral parents. The addition of two electrons to the cyclic carbon framework of [ n]CPPs leads to the characteristic elliptic core distortion and facilitates the internal encapsulation of sizable cationic guests. Molecular and solid-state structure changes, alkali metal binding and unique size-dependent host abilities of the [ n]CPP 2− series with n = 6–12 are discussed. This in-depth analysis opens new perspectives in supramolecular chemistry of [ n]CPPs and promotes their applications in size-selective guest encapsulation and chemical separation.

          Abstract

          The series of doubly-reduced cycloparaphenylenes (CPPs) with increasing dimensions and flexibility shows the size-dependent structural changes and enhanced host abilities.

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          Author and article information

          Journal
          Chem Sci
          Chem Sci
          SC
          CSHCBM
          Chemical Science
          The Royal Society of Chemistry
          2041-6520
          2041-6539
          10 August 2020
          21 September 2020
          10 August 2020
          : 11
          : 35
          : 9395-9401
          Affiliations
          [a] Department of Chemistry, University at Albany, State University of New York Albany NY 12222 USA mpetrukhina@ 123456albany.edu
          [b] Department of Chemistry & Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, University of Oregon Eugene OR 97403 USA rjasti@ 123456uoregon.edu
          Author information
          https://orcid.org/0000-0001-8905-9663
          https://orcid.org/0000-0003-4782-021X
          https://orcid.org/0000-0003-1208-1824
          https://orcid.org/0000-0002-8606-6339
          https://orcid.org/0000-0003-0221-7900
          Article
          d0sc03072d
          10.1039/d0sc03072d
          8161678
          34094205
          3f98f3c2-a284-482b-abf1-7717a720f9e3
          This journal is © The Royal Society of Chemistry
          History
          : 1 June 2020
          : 24 July 2020
          Page count
          Pages: 7
          Funding
          Funded by: National Science Foundation, doi 10.13039/100000001;
          Award ID: CHE-1608628
          Award ID: CHE-2003411
          Award ID: MRI-1726724
          Award ID: CHE-1800586
          Award ID: NSF/CHE-1834750
          Funded by: Deutsche Forschungsgemeinschaft, doi 10.13039/501100001659;
          Award ID: SCHA 2061/1-1
          Funded by: Division of Chemistry, doi 10.13039/100000165;
          Award ID: Unassigned
          Funded by: Division of Materials Research, doi 10.13039/100000078;
          Award ID: Unassigned
          Categories
          Chemistry
          Custom metadata
          Paginated Article

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