Chemistry of Anthracene-Acetylene Oligomers. X. Synthesis, Structures, and Properties of 1,8-Anthrylene-Alkynylene Cyclic Trimers
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Two types of 1,8-anthrylene cyclic trimers with acetylene and diacetylene linkers were synthesized by macrocyclization of the acyclic precursors with Eglinton coupling as examples of the smallest analogues with an odd number of anthracene units. The X-ray analysis and DFT calculations revealed the nonplanar and strained cyclic structures of <I>C</I><SUB>2</SUB> and <I>C<SUB>s</SUB></I> symmetries for the compound with three diacetylene linkers and that with one diacetylene and two acetylene linkers, respectively, with significant bending deformations of acetylene carbons and anthracene moieties. The dynamic behavior of these cyclic compounds was analyzed by VT NMR measurements with the aid of DFT calculations. The NMR chemical shifts and the electronic spectra of the trimers are compared with those of the tetramers and dimers in terms of the orientation of anthracene units and the molecular strains.
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公益社団法人 日本化学会 | 論文
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