Trioxazolo[23]metacyclophane: synthesis, structural analysis, and optical properties
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Published:2022-01-18
Issue:2
Volume:78
Page:81-87
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ISSN:2053-2296
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Container-title:Acta Crystallographica Section C Structural Chemistry
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language:
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Short-container-title:Acta Crystallogr C
Author:
Yu Hao,
Gray Danielle L.ORCID,
Woods Toby J.ORCID,
Moore Jeffrey S.
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.
Funder
MURI (Multi-University Research Initiative) through the Army Research Office (ARO) in the U.S. Department of Defense
Publisher
International Union of Crystallography (IUCr)
Subject
Materials Chemistry,Inorganic Chemistry,Physical and Theoretical Chemistry,Condensed Matter Physics
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