IUCrJ (Nov 2019)

Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds

  • Shalisa M. Oburn,
  • Michael A. Sinnwell,
  • Devin P. Ericson,
  • Eric W. Reinheimer,
  • Davide M. Proserpio,
  • Ryan H. Groeneman,
  • Leonard MacGillivray

DOI
https://doi.org/10.1107/S2052252519011382
Journal volume & issue
Vol. 6, no. 6
pp. 1032 – 1039

Abstract

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A three-dimensional hydrogen-bonded network based on a rare mok topology has been constructed using an organic molecule synthesized in the solid state. The molecule is obtained using a supramolecular protecting-group strategy that is applied to a solid-state [2+2] photodimerization. The photodimerization affords a novel head-to-head cyclobutane product. The cyclobutane possesses tetrahedrally disposed cis-hydrogen-bond donor (phenolic) and cis-hydrogen-bond acceptor (pyridyl) groups. The product self-assembles in the solid state to form a mok network that exhibits twofold interpenetration. The cyclobutane adopts different conformations to provide combinations of hydrogen-bond donor and acceptor sites to conform to the structural requirements of the mok net.

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