Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies

Devin P. Ericson, Zachary P. Zurfluh-Cunningham, Ryan H. Groeneman, Elizabeth Elacqua, Eric W. Reinheimer, Bruce C. Noll, Leonard R. MacGillivray

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Regiocontrolled head-to-head and head-to-tail [2 + 2] photodimerizations of (E)-methyl-3-(pyridin-3-yl)prop-2-enoate are achieved in the solid state using 4,6-di-X-res (where X = Cl, Br, I; res = resorcinol) as small-molecule templates. The components in each co-crystal form discrete, three-component supramolecular assemblies sustained by two O-H···N hydrogen bonds. Whereas the head-to-head photoproduct (rctt)-dimethyl-3,4-bis(pyridin-3-yl)cyclobutane-1,2-dicarboxylate forms using 4,6-di-X-res (X = Cl or Br), the head-to-tail regioisomer (rctt)-dimethyl-2,4-bis(pyridin-3-yl)cyclobutane-1,3-dicarboxylate forms using 4,6-di-I-res. The head-to-tail product is generated via unexpected embraced dimeric assemblies. The stereochemistry of the head-to-tail product is confirmed using single-crystal X-ray diffraction.

Original languageEnglish (US)
Pages (from-to)5744-5748
Number of pages5
JournalCrystal Growth and Design
Volume15
Issue number12
DOIs
StatePublished - Oct 21 2015

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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