Biphenyl Bis[(π-cyclopentadienyl)iron]Dication as an Efficient Cationic Photoinitiator for Epoxy Polymerization

›› 2008, Vol. 16 ›› Issue (5): 819-822.

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Biphenyl Bis[(π-cyclopentadienyl)iron]Dication as an Efficient Cationic Photoinitiator for Epoxy Polymerization

王涛, 张影, 任晓玲

State Key Lab of Chemical Resource Engineering, College of Science, Beijing University of Chemical Technology, Beijing 100029, China

收稿日期:2007-09-25 修回日期:2008-06-24 出版日期:2008-10-28 发布日期:2008-10-28
通讯作者: WANG Tao,E-mail:wangtwj2000@163.com
基金资助:
the National Natural Science Foundation of China(20676012).

Biphenyl Bis[(π-cyclopentadienyl)iron]Dication as an Efficient Cationic Photoinitiator for Epoxy Polymerization

WANG Tao, ZHANG Ying, REN Xiaoling

State Key Lab of Chemical Resource Engineering, College of Science, Beijing University of Chemical Technology, Beijing 100029, China

Received:2007-09-25 Revised:2008-06-24 Online:2008-10-28 Published:2008-10-28
Supported by:
the National Natural Science Foundation of China(20676012).

摘要/Abstract

摘要： Ferrocenium monocations as photoinitiators for cationic photopolymerization suffer from a limitation of low absorption and low reactivity under high-pressure Hg lamp.Here,a ferrocenium dication salt,biphenyl bis [(π-cyclopentadienyl)iron]hexafluorophosphate([bis(Cp-Fe)-biphenyl](PF₆)₂ was synthesized by the ligand exchange reaction between ferrocene and biphenyl.The chemical structure was characterized with FTIR and ¹HNMR. The separation of ferrocenium monocation cyclopentadien-iron-biphenyl hexafluorophosphate([Cp-Fe-biphenyl] PF₆)and dication[bis(Cp-Fe)-biphenyl](PF₆)₂ was carried out by column chromatography.The photoactivity of initiating photopolymerization of epoxide ERl4221 was studied as a cationic photoinitiator.[Bis(Cp-Fe)-biphenyl](PF₆)₂ can efficiently absorb radiation above 300nm and its photoactivity is higher than that of its monocation.

关键词: cationic photopolymerization, [bis(Cp-Fe)-biphenyl](PF₆)₂, photoinitiator, photoactivity

Abstract: Ferrocenium monocations as photoinitiators for cationic photopolymerization suffer from a limitation of low absorption and low reactivity under high-pressure Hg lamp.Here,a ferrocenium dication salt,biphenyl bis [(π-cyclopentadienyl)iron]hexafluorophosphate([bis(Cp-Fe)-biphenyl](PF₆)₂ was synthesized by the ligand exchange reaction between ferrocene and biphenyl.The chemical structure was characterized with FTIR and ¹HNMR. The separation of ferrocenium monocation cyclopentadien-iron-biphenyl hexafluorophosphate([Cp-Fe-biphenyl] PF₆)and dication[bis(Cp-Fe)-biphenyl](PF₆)₂ was carried out by column chromatography.The photoactivity of initiating photopolymerization of epoxide ERl4221 was studied as a cationic photoinitiator.[Bis(Cp-Fe)-biphenyl](PF₆)₂ can efficiently absorb radiation above 300nm and its photoactivity is higher than that of its monocation.

Key words: cationic photopolymerization, [bis(Cp-Fe)-biphenyl](PF₆)₂, photoinitiator, photoactivity

王涛, 张影, 任晓玲. Biphenyl Bis[(π-cyclopentadienyl)iron]Dication as an Efficient Cationic Photoinitiator for Epoxy Polymerization[J]. , 2008, 16(5): 819-822.

WANG Tao, ZHANG Ying, REN Xiaoling. Biphenyl Bis[(π-cyclopentadienyl)iron]Dication as an Efficient Cationic Photoinitiator for Epoxy Polymerization[J]. , 2008, 16(5): 819-822.

参考文献

1 Crivello, J.V., “The discovery and development of onium salt cationic photoinitiator”, J. Polym. Sci.:Part A:Polymer Chemistry, 37, 4241-4254 (1999).
2 Dektar, J.L., Hacker, N.P., John, L.D., Nigel, P.H., “A new mechanism for photodecomposition and acid formation from triphenylsulphonium salts”, J. Chem. Soc. Chem. Commun., 1591-1592 (1987).
3 Castellanos, F., Fouassier, J.P., Priou, C., Cavezzan, J., “Synthesis, reactivity and properties of new diaryliodonium salts as photoinitiators for the cationic polymerization of epoxy silicones”, J. Appl. Polym. Sci., 60, 705-713 (1996).
4 Crivello, J.V., Lam, J.H.W., “Diaryliodonium salts. A new class of photoinitiators for cationic polymerization”, Macromolecules, 10 (6), 1307-1315 (1977).
5 Crivello, J.V., Lam, J.H.W., “Photoinitiated cationic polymerization by dialkyl-4-hydroxyphenylsulfonium salts”, J. Polym. Sci., Polym. Chem. Ed., 18 (3), 1021-1034 (1980).
6 Crivello, J.V., Lam, J.H.W., “A new preparation of triarylsulfonium and selenonium salts via the copper(Ⅱ)-catalyzed arylation of sulfides and selenides with diaryliodonium salts”, J. Org. Chem., 43 (15), 3055-3058 (1978).
7 Davidson, R.S., Goodin, J.W., “Some studies on the photoinitiated cationic polymerization of epoxides”, Eur. Polym. J., 18 (7), 589-595 (1982).
8 Devoe, R.J., Sahyun, M.R.V., Schmidt, E., “Electron transfer sensitized photolysis of 'onium salts”, J. Imaging Sci., 33 (2), 39-43 (1989).
9 Meier, K., Zweifel, H., “Curable composition and it use”, J. Image Sci., 30, 174-176 (1986).
10 Zweifel, H., Meier, K., “Imaging with cationic organomftallic photoinitiators”, Am. Chem. Soc., Div Polym. Chem., 26 (2), 347-348 (1985).
11 Wang, T., Wan, P.Y., Ma, L.J., “Synthesis and characterization of alkoxy and phenoxy-substituted ferrocenium salt cationic photoinitiators”, Chin. J. Chem. Eng., 14 (6), 806-809 (2006).
12 Wang, T., Wang, Z.H., “Cationic photopolymerization of epoxy systems initiated by cyclopentadien-iron-biphenyl hexafluorophosphate ([Cp-Fe-biphenyl]⁺PF₆)”, Polymer Bulletin, 53, 323-327 (2005).
13 Wang, T., Li, B.S., Yu, M., Wan, P.Y., “Iron arene salts as initiators for thermal curing of epoxides by photo-catalysis”, Chin. J. Chem. Eng., 13 (2) , 250-253 (2005).
14 William, H.M. Jr., Ellen, Y.H., David, N.H., “Reaction of ferrocene with polyarornatic molecules. narene bis ((n-cyclopentadieny1)iron) dications (I) Molecular structure”, Journal of the American Chemical Society, 96 (1l), 3603-3609 (1974).
15 Nesmeyanov, A.N., “Nuclear magnetic resonance spectra of arenecyclopentadienyliron compounds”, J. Organomet. Chem., 22, 689-696 (1970)

Biphenyl Bis[(π-cyclopentadienyl)iron]Dication as an Efficient Cationic Photoinitiator for Epoxy Polymerization

Biphenyl Bis[(π-cyclopentadienyl)iron]Dication as an Efficient Cationic Photoinitiator for Epoxy Polymerization

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