Synthesis and Characterization of Thiol-Derivatized Porphyrins and Metalloporphyrin complexes

被引:0
作者
Yuan, Hongping [1 ]
Woo, L. Keith [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
关键词
thiol-porphyrin monolayers; metalloporphyrins; electrocatalysts;
D O I
10.1002/(SICI)1099-1409(199704)1:2<189::AID-JPP23>3.0.CO;2-G
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of thiol-derivatized porphyrins and the corresponding cobalt and zinc complexes were synthesized from 5-(p-aminophenyl)-10,15,20-triphenylporphyrin (H(2)TPP-NH(2)), and 5 alpha,15 alpha-bis(o-aminophenyl)porphyrin (H(2)DPE-(NH(2))(2)). These derivatized porphyrins have a different number of thiol appendages attached via amide linkages at different locations. The thiol-derivatized porphyrins made from H(2)TPP-NH(2), H(2)TPP-NHC(O)(CH(2))(n)SH (n = 2, 4, 5, 10), have one alkyl-thiol appendage attached to the porphyrin through an amide linkage on the p-aminophenyl position. The derivatives made from H(2)DPE-(NH(2))(2) have two alkyl-thiol appendages attached to the porphyrin through amide linkages on the o-aminophenyl positions on the same face of the porphyrin ring. These thiol-derivatized porphyrins are important adsorbates for the preparation of thiol-porphyrin monolayers on gold. (C) 1997 by John Wiley & Sons, Ltd.
引用
收藏
页码:189 / 200
页数:12
相关论文
共 23 条
[1]   A SIMPLIFIED SYNTHESIS FOR MESO-TETRAPHENYLPORPHIN [J].
ADLER, AD ;
LONGO, FR ;
FINARELLI, JD ;
GOLDMACH.J ;
ASSOUR, J ;
KORSAKOF.L .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) :476-+
[2]  
BERSIER PM, 1994, TOP CURR CHEM, V170, P113
[3]   FREE-ENERGY AND TEMPERATURE-DEPENDENCE OF ELECTRON-TRANSFER AT THE METAL-ELECTROLYTE INTERFACE [J].
CHIDSEY, CED .
SCIENCE, 1991, 251 (4996) :919-922
[4]   MERCAPTAN-TAIL PORPHYRINS - SYNTHETIC ANALOGS FOR THE ACTIVE-SITE OF CYTOCHROME-P-450 [J].
COLLMAN, JP ;
GROH, SE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (05) :1391-1403
[5]   Electrocatalytic reduction of dioxygen by diruthenium cofacial diporphyrins axially-bound to a gold-supported, self-assembled monolayer [J].
Collman, JP ;
Ennis, MS ;
Offord, DA ;
Chng, LL ;
Griffin, JH .
INORGANIC CHEMISTRY, 1996, 35 (07) :1751-&
[6]   ELECTRODE CATALYSIS OF THE 4-ELECTRON REDUCTION OF OXYGEN TO WATER BY DICOBALT FACE-TO-FACE PORPHYRINS [J].
COLLMAN, JP ;
DENISEVICH, P ;
KONAI, Y ;
MARROCCO, M ;
KOVAL, C ;
ANSON, FC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (19) :6027-6036
[7]  
CREIGHTON TE, 1993, PROTEINS STRUCTURES, P18
[8]   MECHANISTIC ASPECTS OF THE CATALYTIC REDUCTION OF DIOXYGEN BY COFACIAL METALLOPORPHYRINS [J].
DURAND, RR ;
BENCOSME, CS ;
COLLMAN, JP ;
ANSON, FC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2710-2718
[9]   SULFUR-CONTAINING POLYPEPTIDES .2. SELECTIVE REMOVAL OF S-PROTECTIVE GROUPS FROM SOME L-CYSTEINYL-L-CYSTEINE DERIVATIVES [J].
HISKEY, RG ;
MIZOGUCH.T ;
IGETA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (04) :1188-&
[10]   SULFUR-CONTAINING POLYPEPTIDES .4. SYNTHETIC ROUTES TO CYSTEINE PEPTIDES [J].
HISKEY, RG ;
ADAMS, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2178-&