Synthesis and Crystal Structure of an Aminoxyl Amine Oxide Biradical Compound Bridged by Diphenyl Diacetylene

Dulog L; Kim JS

Korea Polymer Journal, Vol.1, No.2, 96-99, October, 1993

A new biradical compound, 2,2'-(1,3-Butyne-1,4-diyl-di-m-phenylene)-4,4,4',4',5,5,5'5'-octamethyl-3,3'-dioxidobis(2-imidazolin-1-yloxyl)(7) was synthesized and its crystal structure was analyzed to investigate the possibility of the topochemical polymerization. A 9.86 Å of contact distance among the diacetylene functional groups is too apart for the topochemical polymerization. The biradical 7 shows a magnetic susceptibility at room temperature that approaches the calculated paramagnetic susceptibility by Curie''s law.

[References]

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[1] Carlin RL, Magnetochemistry, Springer-Verlag, Berlin (1986)

[2] Mataga N, Theoret. Chim. Acta, 10, 372 (1968)

[3] Ovchinnikov AA, Theoret. Chim. Acta, 47, 297 (1978)

[4] Itoh K, Pure Appl. Chem., 50, 125 (1978)

[5] Teki Y, Takui T, Itoh K, Iwamura H, Kabayashi K, J. Am. Chem. Soc., 108, 2147 (1986)

[6] Miller JS, Dougherty DA, Angew. Chem.-Int. Edit., 101, 985 (1989)

[7] Ovchinnikov AA, Spector VN, Synth. Met., 27, B615 (1988)

[8] Miller JS, Epstein AJ, Reiff WM, Chem. Rev., 88, 201 (1988)

[9] Braun D, Pure Appl. Chem., 30, 41 (1972)

[10] Wegner G, Makromol. Chem., 134, 219 (1970)

[11] Austin WB, Bilow N, Kelleghan WJ, Lau KSY, J. Org. Chem., 46, 2280 (1981)

[12] Sayre R, J. Am. Chem. Soc., 77, 6689 (1955)

[13] Ullman EF, Osiecki JH, Boocock DGB, Darcy R, J. Am. Chem. Soc., 94, 7049 (1972)

[14] Dulog L, Kim JS, Makromol. Chem., 190, 2609 (1989)

[15] Fujii A, Ishida T, Koga N, Iwamura H, Macromolecules, 24, 1077 (1991)

[16] Thakur M, Encyclopedia of Polymer Science and Engineering, H.F. Mark, N.M. Bikales, C.G. Overberger and G. Menges Ed., Vol. 15, p. 362, John Wiley & Sons, New York, U.S.A. (1989)