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Updated: Jul 11, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Engineering control over the conformation of the alkyne-aryl bond by the introduction of cationic charge
Takashi Terashima1, Takuya Nakashima, Tsuyoshi Kawai
1Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan.
Abstract:
A novel arylene-ethynylene molecule has been synthesized. This molecule is more stable in a coplanar form than in a twisted form as in the cases of typical arylene-ethynylene molecules. When the cationic charge was introduced into the pi-conjugated system, the perpendicularly twisted form became more stable than the coplanar state. The conformational change was controlled by introduction and removal of cationic charge, confirmed by the absorption and fluorescence spectroscopy and DFT calculation.
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