Synthesis and characterization of chiral conducting polymers based on polypyrrole

被引:13
作者
Chen, F [1 ]
Akhtar, P [1 ]
KaneMaguire, LAP [1 ]
Wallace, GG [1 ]
机构
[1] UNIV WOLLONGONG,DEPT CHEM,INTELLIGENT POLYMER RES INST,WOLLONGONG,NSW 2522,AUSTRALIA
关键词
D O I
10.1071/C96189
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A range of optically active pyrrole monomers have been synthesized in which a chiral substituent is covalently bonded either to the pyrrole N or C3 ring position, namely (-)-(1R)-4-methyl-N-(1-phenylethyl)pyrrole-3-carboxamide, (+)-(1S)-4-methyl-N-(1-phenylethyl)pyrrole-3- carboxamide, (-)-(1R)-4-methyl-N-(1-naphthylethyl)pyrrole-3-carboxamide, (+)-(1S)-4-methyl-N-(1-naphthylethyl)pyrrole-3-carboxamide, (+)-(2S)-2-(1H-pyrrol-1-yl)propionic acid, (+)-(1S)-N-(1-phenylethyl)pyrrole, and (-)-(1R)-N-(1-phenylethyl)pyrrole. Their chiroptical properties have been established by circular dichroism spectroscopy. Electropolymerization of the three N-substituted pyrrole monomers provided films of chiral conducting polymers, whose electrical and spectroscopic properties are described. Although oxidation of the C3 substituted pyrrole monomers was also facile, electrodeposition was poor and films of the associated polymers could not be obtained.
引用
收藏
页码:939 / 945
页数:7
相关论文
共 21 条
[1]  
ANDERSSON M, 1991, POLYM COMMUN, V32, P546
[2]   EXPERIMENTAL ASPECTS OF USE OF THE QUARTZ CRYSTAL MICROBALANCE IN SOLUTION [J].
BRUCKENSTEIN, S ;
SHAY, M .
ELECTROCHIMICA ACTA, 1985, 30 (10) :1295-1300
[3]   CHIRAL METALS - AMINO ACID-SUBSTITUTED CONDUCTING POLYPYRROLES [J].
DELABOUGLISE, D ;
GARNIER, F .
SYNTHETIC METALS, 1990, 39 (01) :117-120
[4]   POLY(PYRROLE-PHENOTHIAZINE) MODIFIED ELECTRODES - APPLICATION AS PHOTOELECTRODES VIA A CHARGE-TRANSFER COMPLEX [J].
DERONZIER, A ;
ESSAKALLI, M ;
MOUTET, JC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (10) :773-775
[5]   CONDUCTING POLY-N-ALKYLPYRROLE POLYMER-FILMS [J].
DIAZ, AF ;
CASTILLO, J ;
KANAZAWA, KK ;
LOGAN, JA ;
SALMON, M ;
FAJARDO, O .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1982, 133 (02) :233-239
[6]  
DIAZ AF, 1986, HDB CONDUCTING POLYM, V1, pCH3
[7]   CHIRAL METALS - SYNTHESIS AND PROPERTIES OF A NEW CLASS OF CONDUCTING POLYMERS [J].
ELSENBAUMER, RL ;
ECKHARDT, H ;
IQBAL, Z ;
TOTH, J ;
BAUGHMAN, RH .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1985, 118 (1-4) :111-116
[8]   CALIBRATION OF THE ELECTROCHEMICAL QUARTZ CRYSTAL MICROBALANCE [J].
GABRIELLI, C ;
KEDDAM, M ;
TORRESI, R .
JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1991, 138 (09) :2657-2660
[9]   LARGE INDUCED OPTICAL-ACTIVITY IN THE CONDUCTION-BAND OF POLYANILINE DOPED WITH (1S)-(+)-10-CAMPHORSULFONIC ACID [J].
HAVINGA, EE ;
BOUMAN, MM ;
MEIJER, EW ;
POMP, A ;
SIMENON, MMJ .
SYNTHETIC METALS, 1994, 66 (01) :93-97
[10]   SHORT, ENANTIOGENIC SYNTHESES OF (-)-INDOLIZIDINE 167B AND (+)-MONOMORINE [J].
JEFFORD, CW ;
TANG, Q ;
ZASLONA, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (09) :3513-3518