Synthesis and characterization of water-soluble amino fullerene derivatives

被引:100
作者
Richardson, CF [1 ]
Schuster, DI [1 ]
Wilson, SR [1 ]
机构
[1] NYU, Dept Chem, New York, NY 10003 USA
关键词
D O I
10.1021/ol990312a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of amino-substituted methanofullerene derivatives were prepared by mono, tris-, and hexa Bingel-Hirsch reactions using an N-protected malonate derivative, Upon scission of the protecting groups, the e,e,e-tris- and octahedral T-h hexa-methano amino fullerenes were found to be among the most water-soluble fullerene derivatives yet prepared. He-3 NMR data on corresponding adducts of He-3@C-60 helped verify the assigned structures. UV spectral studies confirmed the influence of aggregation on solubility of these adducts in water.
引用
收藏
页码:1011 / 1014
页数:4
相关论文
共 18 条
[1]   A highly water-soluble dendro[60]fullerene [J].
Brettreich, M ;
Hirsch, A .
TETRAHEDRON LETTERS, 1998, 39 (18) :2731-2734
[2]   Efficient cyclopropanation of C-60 starting from malonates [J].
Camps, X ;
Hirsch, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1595-1596
[3]  
Cantor C. R. S. P. R., 1980, BIOPHYSICAL CHEM PAR, P399
[4]   Differentiation of isomers resulting from bisaddition to C-60 using He-3 NMR spectrometry [J].
Cross, RJ ;
JimenezVazquez, HA ;
Lu, Q ;
Saunders, M ;
Schuster, DI ;
Wilson, SR ;
Zhao, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (46) :11454-11459
[5]  
Da Ros T, 1999, CHEM COMMUN, P663
[6]   Carboxyfullerenes as neuroprotective agents [J].
Dugan, LL ;
Turetsky, DM ;
Du, C ;
Lobner, D ;
Wheeler, M ;
Almli, CR ;
Shen, CKF ;
Luh, TY ;
Choi, DW ;
Lin, TS .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (17) :9434-9439
[7]   UNUSUAL REDOX BEHAVIOR OF A WATER-SOLUBLE MALONIC-ACID DERIVATIVE OF C-60 - EVIDENCE FOR POSSIBLE CLUSTER FORMATION [J].
GULDI, DM ;
HUNGERBUHLER, H ;
ASMUS, KD .
JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (36) :13487-13493
[8]   REGIOCHEMISTRY OF MULTIPLE ADDITIONS TO THE FULLERENE CORE - SYNTHESIS OF A T-H-SYMMETRICAL HEXAKISADDUCT OF C-60 WITH BIS(ETHOXYCARBONYL)METHYLENE [J].
HIRSCH, A ;
LAMPARTH, I ;
GROSSER, T ;
KARFUNKEL, HR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :9385-9386
[9]   Water-soluble [60]fullerene-cationic homooxacalix[3]arene complex which is applicable to the photocleavage of DNA [J].
Ikeda, A ;
Hatano, T ;
Kawaguchi, M ;
Suenaga, H ;
Shinkai, S .
CHEMICAL COMMUNICATIONS, 1999, (15) :1403-1404
[10]   Photocycloaddition of cyclic 1,3-diones to C-60 [J].
Jensen, AW ;
Khong, A ;
Saunders, M ;
Wilson, SR ;
Schuster, DI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (31) :7303-7307