Cationic Photopolymerization by Polymeric Triphenyl Phosphonium Salts

Main Article Content

Ideisan I. Abu-Abdoun


Phenacyl triphenylphosphonium and p-nitrobenzyl triphenylphosphonium polymer bound salts with SbF6- counter ions, have been synthesized and examined as polymeric photoinitiators for the cationic photopolymerization of epoxide monomers such as cyclohexene oxide and vinyl monomers such as N-vinyl carbazole and p-methyl styrene. The polymeric phosphonium salts utilized as photocatalysts and were found to be easy to handle and stable when stored far from normal light. Reaction of the nonpolymerizable epoxide compound trans-stilbene oxide with the polymeric phenacyl phosphonium was investigated in dichloromethane solvent and found to gives diphenyl acetaldehyde.

Polymeric triphenyl phosphonium salts, cationic photo initiators, cyclohexene oxide, N-vinyl carbazole, p-methyl styrene, trans-Stilbene oxide acid isomerization.

Article Details

How to Cite
Abu-Abdoun, I. I. (2019). Cationic Photopolymerization by Polymeric Triphenyl Phosphonium Salts. Chemical Science International Journal, 27(4), 1-7.
Original Research Article


Xue Y, Xiao H1, Zhang Y. Antimicrobial polymeric materials with quaternary ammonium and phosphonium salts. Int J Mol Sci. 2015;16(2):3626–3655.

Kanazawa A, Iked T, Endo T. Novel polycationic biocides: Synthesis and antibacterial activity of polymeric phosphonium salts. Journal of Polymer Science Part A: Polymer Chemistry. 1993; 31(2):335-343.

Popa A, Crisan M, Visa A, Ilia G, Brazilian G. Archives of biology and technology. Braz. Arch. Biol. Technol. 2011;1:54.

Bai L, Wang X, Kong S, Song Y, He X, Cong Y. Ionic liquid-crystalline polymer-based quaternary phosphonium salt, Journal Liquid Crystals. 2019;46(4):503-511.

Hodge P, Sherrington DC. Eds. Polymer-supported reactions in organic synthesis; Wiley. Chichers; 1980.

Neckers DC, Abu-Abdoun I. P, P`- Bis (triphenylphosphonium) methyl) benzo-phenone salts as photoinitiators of Free radicals and Cationic polymerization. Macromolecules. 1984;17:2468- 2475.

Alana E, Collis C, Horváth IT. Heterogenization of homogeneous catalytic systems Catal. Sci. Technol, 2011;1:912-919.

Crivello JV. The discovery and development of onium salt cationic photoinitiators. J. Polym. Sci., Polym. Chem. 1999;37:4241.

Sangermano M. Advances in cationic photopolymerization. Pure Appl. Chem. 2012;84(10):2089-2101.

Schlegel LW, Schabel W, Dufour P. In radiation curing in polymer science and technology. Vol I, Fouassier JP, Rabek JF. (Eds.), Elsevier, London. 1993;119.

Abu-Abdoun I, Aal-e-Ali. Cationic Photopolymerization of cyclohexene oxide, European Polymer Journal. 1992;28(1):73-78.

Abu-Abdoun I, Aal-e-Ali. Photo-polymerization of cyclohexene oxide by Phosphonium and Arsonium salts. European Polymer Journal. 1993;29(11): 1445-1450.

Abu-Abdoun I, Aal-e-Ali. Cationic photopolymerization of Styrene by Phosphonium and Arsonium salts. J. Macromol. Sci -Macromolecular Reports. A 1993;30(3&4):327-336.

Abu-Abdoun I, Aal-e-Ali. Cationic photopolymerization of p-Methylstyrene by Phosphonium and Arsonium salts. European Polymer Journal. 1993;29(11): 1439-1443.

House HO. The Acid-catalyzed rearrangement of the stilbene oxides. Journal of the American Chemical Society. 1955;11:77.

Reif DJ, House HO. Diphenyl acetaldehyde formation from reaction of trans stilbene oxide with boron trifluoride etherate in benzene. Org. Synth. 1958; 3826.

El-Hiti AG, Smith K. Rearrangement of epoxides to carbonyl compounds in the presence of reusable acidic zeolite catalysts under mild conditions. Catalysis Letters. 2006;109(1-2):77- 82.

Smith G. Synthesis and ring opening reactions of cis- and trans- oxides. Synthesis. 1984;8:629-656.

Parker RE. Issacs NS. Mechanisms of epoxide reactions. Chem Rev. 1959;59: 737.

Maruoka K, Nagahara S, Ooi T, Yamamoto H. An efficient, catalytic procedure for epoxide rearrangement. Tetrahedron Letters. 1989;30(41):5607-5610.

Anderson AM, Jesse M. Blazek JM, Brian PGJ, Mohan RS. Bismuth (III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketones. Tetrahedron Letters. 2000;41:1527–1530.

Oliverio M, Nardi M, Costanzo P, Di Gioia M, Procopio A. Erbium salts as non-toxic catalysts compatible with alternative reaction media. Sustainability. 2018;10(3): 721.