Trioxazolo[23]metacyclophane: synthesis, structural analysis, and optical properties. Issue 2 (18th January 2022)

• Record Type: Journal Article
• Authors: Yu, Hao; Gray, Danielle L.; Woods, Toby J.; Moore, Jeffrey S.
• Is Part Of: Acta crystallographica. Volume 78:Issue 2(2022)
• Page Start: 81
• Page End: 87
• Publication Date: 2022-01-18
• Subjects: metacyclophane -- conjugated macrocycle -- van Leusen reaction -- gel permeation chromatography -- van Leusen MCRs -- crystal structure; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229622000298
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : The macrocycle trioxazolo[2 3 ]metacyclophane 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 macrocycle possesses a twisted saddle‐like shape and interacts with nearby molecules by various π–π interactions. Abstract : The synthesis and characterization of the conjugated macrocycle trioxazolo[2 3 ]metacyclophane, C27 H15 N3 O3 (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 .