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

Zhou, Zheng; Wei, Zheng; Schaub, Tobias A.; Jasti, Ramesh; Petrukhina, Marina A.

doi:10.1039/d0sc03072d

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

Journal Article · Mon Aug 10 00:00:00 EDT 2020 · Chemical Science

DOI:https://doi.org/10.1039/d0sc03072d· OSTI ID:1673807

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State Univ. of New York (SUNY), Albany, NY (United States)
Univ. of Oregon, Eugene, OR (United States)

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.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: USDOE Office of Science (SC); National Science Foundation (NSF); German Research Foundation (DFG)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1673807

Journal Information:: Chemical Science, Journal Name: Chemical Science Journal Issue: 35 Vol. 11; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: ENGLISH

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