Electroactive 3-(N-phenylpyrazolyl)isoxazoline[4′,5′:1,2][60]fullerene dyads

被引:41
作者
de la Cruz, P
Espíldora, E
García, JJ
de la Hoz, A [1 ]
Langa, F
Martín, N
Sánchez, L
机构
[1] Univ Castilla La Mancha, Fac CC Quim, Dept Quim Organ, E-13071 Ciudad Real, Spain
[2] Univ Castilla La Mancha, Dept Quim Organ, Fac CC Medio Ambiente, Toledo 45071, Spain
[3] Univ Complutense, Dept Quim Organ, Fac Quim, E-28040 Madrid, Spain
关键词
fullerenes; cycloadditions; cyclic voltammetry; microwave heating; isoxazole; pyrazole;
D O I
10.1016/S0040-4039(99)00904-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel C-60-fused isoxazolines have been synthesized by using 1,3-dipolar cycloadditions of pyrazole nitrile oxides, generated in situ, to C-60 under thermal or focused microwave irradiation. The cyclic voltammetry measurements show a strong donor pyrazole ring and a better acceptor ability of the fullerene moiety compared to pristine C-60 The UV-Vis and H-1 NMR spectra suggest a weak CT interaction in the ground state. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4889 / 4892
页数:4
相关论文
共 23 条
[1]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+
[2]   Enhanced acceptor character in fullerene derivatives. Synthesis and electrochemical properties of fulleropyrrolidinium salts [J].
Da Ros, T ;
Prato, M ;
Carano, M ;
Ceroni, P ;
Paolucci, F ;
Roffia, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (45) :11645-11648
[3]  
DaRos T, 1997, CHEM COMMUN, P59
[4]   Synthesis of new C60-donor dyads by reaction of pyrazolylhydrazones with [60]fullerene under microwave irradiation [J].
de la Cruz, P ;
Díaz-Ortiz, A ;
García, JJ ;
Gómez-Escalonilla, MJ ;
de la Hoz, A ;
Langa, F .
TETRAHEDRON LETTERS, 1999, 40 (08) :1587-1590
[5]   Cycloadditions to [60]fullerene using microwave irradiation: A convenient and expeditious procedure. [J].
delaCruz, P ;
delaHoz, A ;
Langa, F ;
Illescas, B ;
Martin, N .
TETRAHEDRON, 1997, 53 (07) :2599-2608
[6]   Electrochemistry of fullerenes and their derivatives [J].
Echegoyen, L ;
Echegoyen, LE .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (09) :593-601
[7]   ISOLATION OF THE HETEROFULLERENE C59N AS ITS DIMER (C59N)(2) [J].
HUMMELEN, JC ;
KNIGHT, B ;
PAVLOVICH, J ;
GONZALEZ, R ;
WUDL, F .
SCIENCE, 1995, 269 (5230) :1554-1556
[8]  
Illescas B, 1998, ELEC SOC S, V98, P1127
[9]   Twofold cycloaddition of [60]fullerene to a bifunctional nitrile oxide [J].
Irngartinger, H ;
Weber, A .
TETRAHEDRON LETTERS, 1996, 37 (24) :4137-4140
[10]   FUNCTIONALIZATION OF C-60 WITH NITRILE OXIDES TO 4,5-DIHYDROISOXAZOLES AND THEIR STRUCTURE DETERMINATION [J].
IRNGARTINGER, H ;
KOHLER, CM ;
HUBERPATZ, U .
CHEMISCHE BERICHTE, 1994, 127 (03) :581-584