Synthesis and Thermal Polymerization of Phenylbutadiynylphenoxy Group Substituted 1.3.5-Tricarbonylbenzene, Cyclotriphosphazene and 1,3,5-Triazine

Chang JY; Lee CB; Baik JH; Yeon JR; Han MJ; Hong SK

Korea Polymer Journal, Vol.4, No.2, 133-138, October, 1996

Chang JY, Lee CB, Baik JH, Yeon JR, Han MJ, Hong SK

Phenylbutadiynylphenoxy group substituted 1,3,5-tricarbonylbenzene (3), cyclotriphosphazene (4), and 1,3,5-triazine (5) were synthesized and their thermal transitions and polymerizations were investigated by using DSC, polarizing optical microscopy, wide angle XRD, and TGA. Compound 3 had a disc-like structure and exhibited polymorphism by heating. Compounds 3 and 4 showed melt transitions followed by thermal polymerization, while compound 5 showed that the polymerization proceeded by 1,4-addition. All polymers, particularly the polymer of comound 4 exhibited excellent thermal stabilities. Compound 4 retained 70% weight even at 800 ℃.

[References]

Wegner GZ, Naturforsch., 24b, 824 (1969)
Advances in Polymer Science, ed. by H.J. Cantow, Springer-Verlag, Berlin, vol. 63 (1984)
Tsibouklis J, Adv. Mater., 7, 407 (1995)
Isuoka A, Okuno T, Ito T, Sugawara T, Sato N, Kamei S, Tohyama K, Mol. Cryst. Liq. Cryst., 226, 201 (1993)
Hammond PT, Rubner MF, Macromolecules, 28(4), 795 (1995)
Schen MA, Kotowski K, Cline J, Polymer, 32, 1843 (1991)
Tieke B, Graf HJ, Wegner G, Naegele B, Ringsdorf H, Banerjie A, Day D, Lando JB, Colloid Polym. Sci., 255, 521 (1977)
Kruchinin VN, Repinsky SM, Sveshnikova LL, Koshkina IM, Auvinen EM, Domnin IN, Thin Solid Films, 240(1-2), 131 (1994)
Batchelder DN, Evans SD, Freeman TL, Haussling L, Ringsdorf H, Wolf H, J. Am. Chem. Soc., 116(3), 1050 (1994)
Kim T, Crooks RM, Tetrahedron Lett., 35, 9501 (1994)
O'Brien DF, Ramaswami V, Encyclopedia of Polymer Science and Engineering, ed. by H.F. Mark, N.M. Bikales, C.G. Overberger, and G. Menges, 2nd ed., Wiley, New York, vol. 17, pp. 108 (1987)
Peek BM, Callahan JH, Namboodiri K, Singh A, Gaber BP, Macromolecules, 27(1), 292 (1994)
Chang IY, Ji HJ, Han MJ, Bull. Korean Chem. Soc., 16, 674 (1995)
Sonogashira K, Tohda Y, Hagihara N, Tetrahedron Lett., 4467 (1975)
Dieck HA, Heck RF, J. Org. Chem., 93, 259 (1975)
Takahashi S, Kuroyama Y, Sonogashira K, Hagihara N, Synthesis, 627 (1980)
austin WB, Bilow N, Kellaghan WJ, Lau KSY, J. Org. Chem., 46, 2280 (1981)
Chang JY, Rhee SB, Cheong S, Yoon M, Macromolecules, 25, 2666 (1992)

[1] Wegner GZ, Naturforsch., 24b, 824 (1969)

[2] Advances in Polymer Science, ed. by H.J. Cantow, Springer-Verlag, Berlin, vol. 63 (1984)

[3] Tsibouklis J, Adv. Mater., 7, 407 (1995)

[4] Isuoka A, Okuno T, Ito T, Sugawara T, Sato N, Kamei S, Tohyama K, Mol. Cryst. Liq. Cryst., 226, 201 (1993)

[5] Hammond PT, Rubner MF, Macromolecules, 28(4), 795 (1995)

[6] Schen MA, Kotowski K, Cline J, Polymer, 32, 1843 (1991)

[7] Tieke B, Graf HJ, Wegner G, Naegele B, Ringsdorf H, Banerjie A, Day D, Lando JB, Colloid Polym. Sci., 255, 521 (1977)

[8] Kruchinin VN, Repinsky SM, Sveshnikova LL, Koshkina IM, Auvinen EM, Domnin IN, Thin Solid Films, 240(1-2), 131 (1994)

[9] Batchelder DN, Evans SD, Freeman TL, Haussling L, Ringsdorf H, Wolf H, J. Am. Chem. Soc., 116(3), 1050 (1994)

[10] Kim T, Crooks RM, Tetrahedron Lett., 35, 9501 (1994)

[11] O'Brien DF, Ramaswami V, Encyclopedia of Polymer Science and Engineering, ed. by H.F. Mark, N.M. Bikales, C.G. Overberger, and G. Menges, 2nd ed., Wiley, New York, vol. 17, pp. 108 (1987)

[12] Peek BM, Callahan JH, Namboodiri K, Singh A, Gaber BP, Macromolecules, 27(1), 292 (1994)

[13] Chang IY, Ji HJ, Han MJ, Bull. Korean Chem. Soc., 16, 674 (1995)

[14] Sonogashira K, Tohda Y, Hagihara N, Tetrahedron Lett., 4467 (1975)

[15] Dieck HA, Heck RF, J. Org. Chem., 93, 259 (1975)

[16] Takahashi S, Kuroyama Y, Sonogashira K, Hagihara N, Synthesis, 627 (1980)

[17] austin WB, Bilow N, Kellaghan WJ, Lau KSY, J. Org. Chem., 46, 2280 (1981)

[18] Chang JY, Rhee SB, Cheong S, Yoon M, Macromolecules, 25, 2666 (1992)