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Progress in Chemistry 2015, Vol. 27 Issue (7): 853-860 DOI: 10.7536/PC141234 Previous Articles   Next Articles

• Review and comments •

Ferrocene-Based Epoxy Derivatives

Wang Jianjun*1, Ding Hengchun1, Ni Peihong1, Dai Lixing1, Gao Qiang*2   

  1. 1. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China;
    2. Key Laboratory of Eco-textiles, Ministry of Education, College of Textile & Clothing, Jiangnan University, Wuxi 214122, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 20874068), and the Open Project Program of Key Laboratory of Eco-textiles, Ministry of Education, Jiangnan University (No. KLET1303).
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Ferrocene-based epoxy of the special chemical structure is composed of epoxy and ferrocene. These materials behave as structurally diverse monomers and multifunctional polymers. In recent years, more attention is focused on synthetic approaches and applications due to their high chemical activity and multifunctionality. More than twenty small molecules of ferrocene-based epoxy have been synthesized via ferrocenyl aldehydes, ketones, alkene, chlorohydrins, diols, or chloroacetyl intermediates, and polymerized derivatives have also been developed by ferrocene-modified epoxy polymers or free radical copolymerization of glycidyl ether and vinylferrocene. This review intends to offer relevant synthetic strategies for the preparation of covalent systems based on epoxy and ferrocene. Particular attention has been paid to understand the fundamental stability of these systems. The vicinal epoxy facilitates the formation of ferrocenyl carbonium ions, and is labile toward ring opening and consequent isomerization to the aldehyde. A variety of architectures have a wide range of potential applications in areas such as functional materials, biomedical mediators, chiral ferrocenyl ligands, burn-rate catalysts and antitumor agents, among others. Detailed examples with different chemical structures of polymers are provided to illustrate about their applications. Finally, the future development at the surface and interface of materials is prospected.

Contents
1 Introduction
2 Stability of ferrocene-based epoxys
3 Synthesis of ferrocene-based epoxys
3.1 Base catalysis chlorohydrins
3.2 Corey-Chayovsky reaction
3.3 Sulphur ylide-mediated epoxidation
3.4 Dimethyldioxirane oxidation
3.5 Vicinal diols dehydration
3.6 Darzens reaction
4 Applications of ferrocene-based epoxys
4.1 Functional polymers or resins
4.2 Biomedical mediators
4.3 Chiral ferrocenyl ligands
4.4 Burn-rate catalysts
4.5 Antitumor agents
5 Conclusion

Key words: ferrocene, epoxy, functional polymers, burning rate catalysts

CLC Number: 

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Ferrocene-Based Epoxy Derivatives