Synthetic routes to porphyrins bearing fused rings

被引:122
作者
Fox, Simon [1 ]
Boyle, Ross W. [1 ]
机构
[1] Univ Hull, Dept Chem, Kingston Upon Hull HU6 7RX, E Yorks, England
关键词
D O I
10.1016/j.tet.2006.08.021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthetic routes to porphyrins bearing fused rings, which can effect porphyrins by alternating their optical properties, both ground state and excited state, coordination chemistry and redox behavior , are discussed. Porphyrines with fused rings can be formed via several routes such as intramolecular cyclizations including metal-mediated cyclization and acid and base-catalyzed cyclization, or via intermolecular reactions, which includes Diels-Alder reactions, cycloaddition reactions or Bergman cyclization of porphyrine diynes. Fused porphyrine macrocycles are of great interest as potential molecular wires. These can be used to assemble heterodyads, in which a porphyrin and another chromophore are fused two neighboring β-carbons. It can give rise to the extended conjugation of the aromatic π-system and led to the development of many new products.
引用
收藏
页码:10039 / 10054
页数:16
相关论文
共 97 条
[1]   AGGREGATION OF A BACTERIOCHLOROPHYLLIDE-D - DIRECT EVIDENCE FOR A NONSYMMETRIC AGGREGATE IN SOLUTION [J].
ABRAHAM, RJ ;
SMITH, KM ;
GOFF, DA ;
BOBE, FW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (04) :1085-1087
[2]  
Aihara H, 2001, ANGEW CHEM INT EDIT, V40, P3439, DOI 10.1002/1521-3773(20010917)40:18<3439::AID-ANIE3439>3.0.CO
[3]  
2-Z
[4]  
ARANTI N, 2000, ANGEW CHEM INT EDIT, V39, P1458
[5]   WITTIG CONDENSATION PRODUCTS FROM NICKEL MESO-FORMYL-OCTAETHYLPORPHYRIN AND MESO-FORMYL-AETIOPORPHYRIN-I AND SOME CYCLIZATION REACTIONS [J].
ARNOLD, DP ;
GAETEHOLMES, R ;
JOHNSON, AW ;
SMITH, ARP ;
WILLIAMS, GA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (12) :1660-1670
[6]   ANOMALOUS DOUBLE CYCLIZATION REACTIONS OF BETA-FORMYLPORPHYRINS [J].
BARLOY, L ;
DOLPHIN, D ;
DUPRE, D ;
WIJESEKERA, TP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :7976-7985
[7]  
BARTON DHR, 1990, TETRAHEDRON, V46, P7587
[8]   REACTIVE 1,4-DEHYDROAROMATICS [J].
BERGMAN, RG .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31
[9]  
Boyd PDW, 1999, CHEM COMMUN, P637
[10]   5,15-DIPHENYL-7-OXOBENZOCHLORINS - NOVEL LONG-WAVELENGTH ABSORBING PHOTOSENSITIZERS FOR PHOTODYNAMIC THERAPY [J].
BOYLE, RW ;
DOLPHIN, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (21) :2463-2464