Trioxazolo[23]metacyclophane: Synthesis, structural analysis, and optical properties

Hao Yu, Danielle L. Gray, Toby J. Woods, Jeffrey S. Moore

Research output: Contribution to journalArticlepeer-review


The synthesis and characterization of the conjugated macrocycle trioxazolo[23]metacyclophane, C27H15N3O3 (M), is reported. The macrocycle was synthesized in three steps by the multicomponent van Leusen reaction and consists of meta-linked phenylenes connected through positions 4 and 5 of an oxazole heterocyclic ring. The molecular structure was investigated by NMR spectroscopy, mass spectrometry, gel permeation chromatography (GPC), and single-crystal X-ray crystallography. X-ray diffraction (XRD) analysis shows that M possesses a twisted saddle-like shape and interacts with nearby molecules by various - interactions. Absorption and emission spectroscopy and density functional theory (DFT) calculations were further used to study the electronic properties of M.

Original languageEnglish (US)
Pages (from-to)81-87
Number of pages7
JournalActa Crystallographica Section C: Structural Chemistry
StatePublished - Feb 1 2022


  • conjugated macrocycle
  • crystal structure
  • gel permeation chromatography
  • metacyclophane
  • van Leusen MCRs
  • van Leusen reaction

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry


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