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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
Published on: September 26, 2016
Trioxazolo[23]metacyclophane: synthesis, structural analysis, and optical properties
Hao Yu1, Danielle L Gray2, Toby J Woods2
1Department of Chemical and Biomolecular Engineering, University of Illinois at Urbana-Champaign, 600 S. Mathews Ave., Urbana, IL 61801, USA.
Abstract:
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 π-π interactions. Absorption and emission spectroscopy and density functional theory (DFT) calculations were further used to study the electronic properties of M.
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