Electrochemical properties of soluble fullerene derivatives

被引:7
作者
Carano, M
Ceroni, P
Da Ros, T
Kordatos, K
Tomberli, V
Paolucci, F
Prato, M
Roffia, S
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Univ Trieste, Dipartimento Sci Farmaceut, I-34127 Trieste, Italy
关键词
fullerenes; fullerene derivatives; fulleropyrrolidines; electrochemistry; polythiophenes;
D O I
10.1016/S0013-4686(00)00581-8
中图分类号
O646 [电化学、电解、磁化学];
学科分类号
081704 ;
摘要
The Family of fullerene derivatives obtained by 1,3-dipolar cycloaddition of azomethine ylides to C-60 is colloquially termed fulleropyrrolidines. In this payer, we report the synthesis and the electrochemical properties of a series of fulleropyrrolidine derivatives. All compounds are characterized by the presence of a solubilizing mTEG group. In addition, a derivative containing a thiophene moiety, covalently attached to the pyrrolidine ring has been studied. Cyclic voltammetry measurements, performed also at low temperatures, allowed the observation of five fullerene-centered reductions for all the species. Adsorption phenomena, however, were found associated to the last reduction processes in the thiophene-fulleropyrrolidine conjugate. Moreover, thanks to the increased solubility of the latter species in polar solvents (acetonitrile-dichloromethane mixtures) its anodic polymerization was carried out, leading to a conducting film still retaining the redox properties of the fullerene derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:265 / 269
页数:5
相关论文
共 30 条
[1]   ORGANIC MOLECULAR SOFT FERROMAGNETISM IN A FULLERENE-C60 [J].
ALLEMAND, PM ;
KHEMANI, KC ;
KOCH, A ;
WUDL, F ;
HOLCZER, K ;
DONOVAN, S ;
GRUNER, G ;
THOMPSON, JD .
SCIENCE, 1991, 253 (5017) :301-303
[2]  
ANDERSON HL, 1994, ANGEW CHEM INT EDIT, V33, P1628, DOI 10.1002/anie.199416281
[3]   The first ''charm bracelet'' conjugated polymer: An electroconducting polythiophene with covalently bound fullerene moieties [J].
Benincori, T ;
Brenna, E ;
Sannicolo, F ;
Trimarco, L ;
Zotti, G ;
Sozzani, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (06) :648-651
[4]  
COSNIER S, 1990, NEW J CHEM, V14, P831
[5]  
Da Ros T, 1999, CHEM COMMUN, P663
[6]   Easy access to water-soluble fullerene derivatives via 1,3-dipolar cycloadditions of azomethine ylides to C-60 [J].
DaRos, T ;
Prato, M ;
Novello, F ;
Maggini, M ;
Banfi, E .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9070-9072
[7]   ELECTROCHEMICAL SYNTHESIS OF A REDOX-ACTIVE POLYMER-BASED ON BUCKMINSTERFULLERENE EPOXIDE [J].
FEDURCO, M ;
COSTA, DA ;
BALCH, AL ;
FAWCETT, WR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (02) :194-196
[8]  
HIRSCH A, 1999, TOP CURR CHEM, V199
[9]  
Hirsch A, 1994, CHEM FULLERENES
[10]   OPTICAL LIMITING WITH C-60 IN POLYMETHYL METHACRYLATE [J].
KOST, A ;
TUTT, L ;
KLEIN, MB ;
DOUGHERTY, TK ;
ELIAS, WE .
OPTICS LETTERS, 1993, 18 (05) :334-336