Site-isolated porphyrin catalysts in imprinted polymers

被引:52
作者
Burri, E [1 ]
Öhm, M [1 ]
Daguenet, C [1 ]
Severin, K [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, CH-1015 Lausanne, Switzerland
关键词
heterogeneous catalysis; molecular imprinting; oxidation; prophyrin complexes; ruthenium;
D O I
10.1002/chem.200500375
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A meso-tetraaryl ruthenium porphyrin complex having four polymerizable vinylbenzoxy groups (2) has been synthesized by reaction of pyrrole with 4-(vinylbenzoxy)benzaldehyde and subsequent metalation with [Ru-3(CO)(12)]. The porphyrin complex was immobilized by copolymerization with ethylene glycol dimethacrylate. The resulting polymer P2 was found to catalyze the oxidation of alcohols alkanes with 2,6-dichloropyridine N-oxide without activation by mineral acids. Under similar conditions, the homogeneous catalyst 2 was completely inefficient. By using diphenylamino-methane and 1-aminoadamantane as coordinatively bound templates during the polymerization procedure, the molecularly imprinted polymers P3 and P4 have been synthesized. Compared with the polymer P2, the imprinted catalysts displayed a significantly increased activity with rate enhancements of up to a factor of 16.
引用
收藏
页码:5055 / 5061
页数:7
相关论文
共 79 条
[41]   Ruthenium porphyrin encapsulated in modified mesoporous molecular sieve MCM-41 for alkene oxidation [J].
Liu, CJ ;
Li, SG ;
Pang, WQ ;
Che, CM .
CHEMICAL COMMUNICATIONS, 1997, (01) :65-66
[42]   Ruthenium meso-tetrakis(2,6-dichlorophenyl)porphyrin complex immobilized in mesoporous MCM-41 as a heterogeneous catalyst for selective alkene epoxidations [J].
Liu, CJ ;
Yu, WY ;
Li, SG ;
Che, CM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7364-7369
[43]   Influence of polymerization temperature on the molecular recognition of imprinted polymers [J].
Lu, Y ;
Li, CX ;
Wang, XD ;
Sun, PC ;
Xing, XH .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2004, 804 (01) :53-59
[44]   THE CRYSTAL AND MOLECULAR-STRUCTURE OF NEW TETRAVALENT RUTHENIUM PORPHYRIN - MU-OXO-BIS[(OCTAETHYLPORPHINATO)RUTHENIUM(IV) HYDROXIDE] [J].
MASUDA, H ;
TAGA, T ;
OSAKI, K ;
SUGIMOTO, H ;
MORI, M ;
OGOSHI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2199-2203
[45]   Molecularly imprinted receptor having metalloporphyrin-based signaling binding site [J].
Matsui, J ;
Tachibana, Y ;
Takeuchi, T .
ANALYTICAL COMMUNICATIONS, 1998, 35 (07) :225-227
[46]   Molecularly imprinted polymer as 9-ethyladenine receptor having a porphyrin-based recognition center [J].
Matsui, J ;
Higashi, M ;
Takeuchi, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) :5218-5219
[47]   METALLOPORPHYRINS AS VERSATILE CATALYSTS FOR OXIDATION REACTIONS AND OXIDATIVE DNA CLEAVAGE [J].
MEUNIER, B .
CHEMICAL REVIEWS, 1992, 92 (06) :1411-1456
[48]   RADIOLYTIC STUDIES OF THE REDOX REACTIONS OF RUTHENIUM PORPHYRINS [J].
MOSSERI, S ;
NETA, P ;
HAMBRIGHT, P .
JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (06) :2358-2362
[49]   A ruthenium porphyrin catalyst immobilized in a highly cross-linked polymer [J].
Nestler, O ;
Severin, K .
ORGANIC LETTERS, 2001, 3 (24) :3907-3909
[50]  
OHTAKE H, 1995, HETEROCYCLES, V40, P867