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Engineering Control over the Conformation of the Alkyne−Aryl Bond by the Introduction of Cationic Charge
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- Takashi Terashima
- Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
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- Takuya Nakashima
- Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
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- Tsuyoshi Kawai
- Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
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Description
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.
Journal
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- Organic Letters
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Organic Letters 9 (21), 4195-4198, 2007-09-18
American Chemical Society (ACS)
