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      Structural deformation and host–guest properties of doubly-reduced cycloparaphenylenes, [n]CPPs2− (n = 6, 8, 10, and 12)

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          Abstract

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

          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.

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          Author and article information

          Contributors
          Journal
          CSHCBM
          Chemical Science
          Chem. Sci.
          Royal Society of Chemistry (RSC)
          2041-6520
          2041-6539
          September 16 2020
          2020
          : 11
          : 35
          : 9395-9401
          Affiliations
          [1 ]Department of Chemistry
          [2 ]University at Albany
          [3 ]State University of New York
          [4 ]Albany
          [5 ]USA
          [6 ]Department of Chemistry & Biochemistry
          [7 ]Materials Science Institute
          [8 ]Knight Campus for Accelerating Scientific Impact
          [9 ]University of Oregon
          [10 ]Eugene
          Article
          10.1039/D0SC03072D
          © 2020

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