Synthesis and polymerization studies of 3-(+) and (−)-menthyl carboxylate pyrroles

作者: Richard C. Foitzik , Elspeth K. Bowen , Amelia M. Taylor , Frederick M. Pfeffer , Akif Kaynak

DOI: 10.1016/J.SYNTHMET.2007.09.003

关键词:

摘要: The synthesis of 3-(−)- and 3-(+)-menthyl carboxylate pyrrole was achieved in four high yielding steps, including the triisopropylsilyl (TIPS) protection nitrogen, bromination 3-position, lithium halogen exchange followed by reaction with menthyl chloroformate, finally de-protection. Chemical polymerization both TIPS protected, non-protected, pyrroles performed resulting polymers exhibited conductivity ranging from 0.6 to 2.3 S/cm. Polymerization 3-menthyl-N-TIPS on surface wool using solution mist methods.

参考文章(23)
Nathan S. Lewis, Margaret A. Ryan, Low power, lightweight vapor sensing using arrays of conducting polymer composite chemically-sensitive resistors. Enantiomer. ,vol. 6, pp. 159- 170 ,(2001)
Vickie Aboutanos, Parveen Akhtar, Leon A. P. Kane-Maguire, Gordon G. Wallace, Optically active polypyrroles containing chiral dopant anions Australian Journal of Chemistry. ,vol. 53, pp. 83- 87 ,(2000) , 10.1071/CH99105
Katsumi Yoshino, Kazuya Tada, Kenji Yoshimoto, Masayoshi Yoshida, Tsuyoshi Kawai, Hisashi Araki, Maki Hamaguchi, Anvar Zakhidov, Electrical and optical properties of molecularly doped conducting polymers Synthetic Metals. ,vol. 78, pp. 301- 312 ,(1996) , 10.1016/0379-6779(96)80154-8
Manuel Salmón, Miguel Saloma, Gerard Bidan, E.M. Genies, Route to chemically modified chiral electrodes: synthesis and properties of optically active pyrrole monomers Electrochimica Acta. ,vol. 34, pp. 117- 120 ,(1989) , 10.1016/0013-4686(89)87075-6
B. Piro, J. Haccoun, M.C. Pham, L.D. Tran, A.Rubin, H. Perrot, C. Gabrielli, Study of the DNA hybridization transduction behavior of a quinone-containing electroactive polymer by cyclic voltammetry and electrochemical impedance spectroscopy Journal of Electroanalytical Chemistry. ,vol. 577, pp. 155- 165 ,(2005) , 10.1016/J.JELECHEM.2004.12.002
D. Delabouglise, F. Garnier, Chiral metals: amino acid-substituted conducting polypyrroles Synthetic Metals. ,vol. 39, pp. 117- 120 ,(1990) , 10.1016/0379-6779(90)90205-Y
Dean M. Tigelaar, Wonpil Lee, Kenn A. Bates, Alexey Saprigin, Vladimir N. Prigodin, Xiaolin Cao, Laurence A. Nafie, Matthew S. Platz, Arthur J. Epstein, Role of Solvent and Secondary Doping in Polyaniline Films Doped with Chiral Camphorsulfonic Acid: Preparation of a Chiral Metal Chemistry of Materials. ,vol. 14, pp. 1430- 1438 ,(2002) , 10.1021/CM011567X