42858-85-5Relevant academic research and scientific papers
Powerful oxidizing properties of a planar [8]annulene: Tetrakis(perfluorocyclobuta)cyclooctatetraene) and its radical anion
Gerson, Fabian,Huber, Walter,Merstetter, Pascal,Persy, Gaby,Soulen, Robert L.,Spoendlin, Christoph,Wirz, Jakob
, p. 1434 - 1444 (1999)
The central eight-membered ring of tetrakis(perfluorocyclobuta)cyclooctatetraene (1) is flat both in the crystal and in solution, but tetrakis(perfluorocyclopenta)cyclooctatctracne (2) assumes a tub shape similar to that of parent cyclooctatetraene. This sterically induced structural difference strongly affects the physical properties of compounds 1 and 2. The first and second reduction potentials of 1 in solution, + 0.79 and + 0.14 V vs. SCE, are considerably more positive than the corresponding values, + 0.20 and - 0.21 V, of 2. Accordingly, mere contact with Hg metal in N,N-dimethylformamide converts 1 to an unusually stable radical anion 1'- that is persistent in air. The temperature- independent coupling constant, a(F) = + 0.320 mT, of the sixteen equivalent [β19F-nuclei in 1- is much smaller than the expected value, and the g factor of 1'- is markedly lower than those generally found for structurally related radical anions. In contrast, the characteristic data for 2-, generated from 2 with K metal in 1,2-dimethoxyethane, comply with the expected data. The coupling constants a(F) = + 0.976 and +0.935 mT, each of eight β-19F-nuclei in 2-, average +0.951 mT upon raising the temperature from 220 to 260 K. The gas-phase electron affinity of 1, A = 3.4 ± 0.2 eV, which was estimated from the reduction potential in solution and from charge- transfer absorption spectra obtained from a series of methylated benzenes and naphthalenes, is among the highest known for neutral organic molecules.
Reaction of methanol with perfluorotetracyclobuta-1,3,5,7-cyclooctatetraene
Cullen, William R.,Rettig, Steven J.,Moore, Alice E.,Soulen, Robert L.
, p. 121 - 124 (1996)
Perfluorotetracyclobuteno-1,3,5,7-cyclooctatetraene (PCOT) is a planar and centrosymmetric molecule which possesses an extraordinary electron affinity due to the planarity of the eight π-electron system and the cumulative electron-withdrawing effects of the 16 fluorine atoms. An improved method for the synthesis of PCOT and the product resulting from the spontaneous reaction of PCOT with excess alcohol is reported. Crystal structures of the methyl (1) and ethyl (2) derivatives are described.
