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Updated: Jun 25, 2026

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
Published on: September 26, 2016
Perfluoroaryltetrahedranes: tetrahedranes with extended sigma-pi conjugation
Masaaki Nakamoto1, Yusuke Inagaki, Motoaki Nishina
1Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
Abstract:
The first stable aryl-substituted tetrahedrane derivatives 4-6 were synthesized by the reaction of tris(trimethylsilyl)tetrahedranyllithium with hexafluorobenzene or [(pentafluorophenyl)ethynyl]benzene in THF. Tetrahedranes having the fluoroaryl groups as electron-withdrawing substituents were found to be thermally stable up to 170 degrees C. X-ray analyses of 4 and 6 and UV-vis absorption spectra of 4-6 suggest sigma-pi conjugation between the strained tetrahedrane core and the benzene ring, which causes a considerable bathochromic shift.
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