Cationic Polymerization Induced by Tris-(p-bromophenyl) Amine Cation-Radical Salts

Ideisan I. Abu-Abdoun

doi:10.6000/1929-5995.2019.08.04

Authors

Ideisan I. Abu-Abdoun Department of Chemistry, University of Sharjah, Sharjah P.O. Box: 27272, UAE

DOI:

https://doi.org/10.6000/1929-5995.2019.08.04

Keywords:

Tris-(p-bromophenyl) amine, Cation radical salts, Cationic polymerization, N-vinyl carbazole, Cyclohexene oxide. Tetrahydrofuran

Abstract

Substituted triphenylamine cation radical salts having anions of the type SbF₆^-, PF₆^-, BF₄^- and SbCl₆^-, were prepared and used to initiate cationic polymerization of cyclohexene oxide (CHO), tetrahydrofuran (THF), and N-vinyl carbazole (NVC), thermally in dichloromethane at room temperature. Experimental results are presented to show the effects of salt counter ion, concentration, and polymerization conditions on the yield and the molecular weight of the obtained polymer. THF polymerization was enhanced by photolysis of the reaction mixture for short time. A general mechanism for the polymerization by cation-radical salts of substituted triphenylamine is proposed.

References

Dadashi-Silab S, Doran S, Yagci Y. Photoinduced Electron Transfer Reactions for Macromolecular Syntheses. Chem Rev 2016; 116(17): 10212-10275. https://doi.org/10.1021/acs.chemrev.5b00586 DOI: https://doi.org/10.1021/acs.chemrev.5b00586

Sangermano M. Advances in cationic photopolymerization. Pure Appl Chem 2012; 84(10): 2089-2101. https://doi.org/10.1351/PAC-CON-12-04-11 DOI: https://doi.org/10.1351/PAC-CON-12-04-11

Crivello JV. The discovery and development of onium salt cationic photoinitiators. J Polym Sci Polym Chem 1999; 37: 4241. https://doi.org/10.1002/(SICI)1099-0518(19991201)37:23<4241::AID-POLA1>3.0.CO;2-R DOI: https://doi.org/10.1002/(SICI)1099-0518(19991201)37:23<4241::AID-POLA1>3.0.CO;2-R

Schlegel L, Schabel W, Dufour P. In Radiation Curing in Polymer Science and Technology. Fouassier JP, Rabek JF, Eds. Elsevier, London 1993; Vol. I: p. 119.

Abu-Abdoun I, Aal-e-Ali. Photopolymerization of cyclohexene oxide by Phosphonium and Arsonium salts. European Polymer Journal 1993; 29(11): 1445-1450. https://doi.org/10.1016/0014-3057(93)90056-L DOI: https://doi.org/10.1016/0014-3057(93)90056-L

Abu-Abdoun I, Ledwith A. Cationic polymerization photochemically and thermally induced by phenothiazine cation radical salts. Europ Polym J 1997; 33: 1671-1677. https://doi.org/10.1016/S0014-3057(97)00044-X DOI: https://doi.org/10.1016/S0014-3057(97)00044-X

Abu-Abdoun I, Ledwith A. Photochemically and Thermally Induced polymerization by N, N, N, N Tetraphenylene amine Cation radical Salts. J Macromol Sci - Pure and Appl Chem 1998; A35(4): 673-690. https://doi.org/10.1080/10601329808002005 DOI: https://doi.org/10.1080/10601329808002005

Tokito H, Tanaka A, Okada Y, Taga. High‐temperature operation of an electroluminescent device fabricated using a novel triphenylamine derivative. Appl Phys Lett 1996; 69(7): 878. https://doi.org/10.1063/1.117974 DOI: https://doi.org/10.1063/1.117974

Kimura M, Inoue S, Shimada K, Tokito S, Noda K, Taga Y, Sawaki Y. Spirocycle-incorporated triphenylamine derivatives as an advanced organic electroluminescent material. Chem Lett 2000; 2: 192-193. https://doi.org/10.1246/cl.2000.192 DOI: https://doi.org/10.1246/cl.2000.192

Fehervari AF, Kagumba LC, Hadjikyriacou S, Chen F, Gaudiana RA. Ultraviolet-emitting conjugated polymer poly(9,9′-alkyl-3,6-silafluorene) with a wide band gap of 4.0 eV. J Appl Polym Sci 2003; 87: 1634. https://doi.org/10.1002/app.11606 DOI: https://doi.org/10.1002/app.11606

Bawn CH, Bell FA, Ledwith A. Oxidation by a cation radical: electron transfer from 1,1-bis-(p-dimethylaminophenyl) ethylene. Chem Comm 1968; 599. https://doi.org/10.1039/c19680000599 DOI: https://doi.org/10.1039/c19680000599

Walter RI. J Amer Chem Soc 1966; 88: 1923. https://doi.org/10.1021/ja00961a014 DOI: https://doi.org/10.1021/ja00961a014

Ledwith A, Sherrington DC., Macromolecular Synthesis 1972; 4: 183.

Croucher TG, Walter RE. Polymer 1976; 17: 205. https://doi.org/10.1016/0032-3861(76)90101-4 DOI: https://doi.org/10.1016/0032-3861(76)90101-4

Dreyfuss MP. p‐Chlorophenyldiazonium hexafluorophos-phate as a catalyst in the polymerization of tetrahydrofuran and other cyclic ethers. J Poly Sci Part-A Poly Chem Ed 1966; 4: 92179-2200. https://doi.org/10.1002/pol.1966.150040913 DOI: https://doi.org/10.1002/pol.1966.150040913

Yagci Y, Ledwith A. Mechanistic and Kinetic-Studies on the Photoinitiated Polymerization of Tetrahydrofuran. J Poly Sci Part-A Poly Chem Ed 1988; 26(7): 1911-1918. https://doi.org/10.1002/pola.1988.080260717 DOI: https://doi.org/10.1002/pola.1988.080260717

Abu-Abdoun I, Aal-e-Ali. Cationic Photopolymerization of cyclohexene oxide. European Polymer Journal 1992; 28(1): 73-78. https://doi.org/10.1016/0014-3057(92)90239-X DOI: https://doi.org/10.1016/0014-3057(92)90239-X

Svanholm U, Parker VD. Kinetics and mechanisms of the reactions of organic cation radicals and dications. IV. First-and second-order reactions of thianthrene cation radical with phenol. J Amer Chem Soc 1976; 98: 997-1002. https://doi.org/10.1021/ja00420a023 DOI: https://doi.org/10.1021/ja00420a023