Synthesis of bipyridylene-bridged bisporphyrin by nickel-mediated coupling reaction: ON-OFF control of cofacial porphyrin unit by reversible complexation

被引:46
作者
Tomohiro, Y
Satake, A
Kobuke, Y
机构
[1] Nara Inst Sci & Technol, Grad Sch Mat Sci, Nara 6300101, Japan
[2] Japan Sci & Technol Corp, JST, CREST, Nara 6300101, Japan
关键词
D O I
10.1021/jo015852b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel bipyridylene-bridged bisporphyrin la, in which two porphyrin units were attached directly to symmetrical 4,4'-positions of the 2,2'-bipyridyl group, was synthesized by a nickel(0)-mediated homocoupling reaction of 5,10,15-tris(n-heptyl)-20-(2'-bromo-4'-pyridyl)porphyrinatozinc (3a) in 58% yield. Spatial geometries of two porphyrins in la were regulated by reversible complexation of the bipyridyl part with PdCl(2). Thus, the addition of 2.2 equiv of palladium chloride to la converted the freely rotating conformation to the cofacial bisporphyrin 2a. The subsequent addition of 4,4'-dimethyl-2,2'-bipyridine 9 regenerated the initial bisporphyrin 1a.
引用
收藏
页码:8442 / 8446
页数:5
相关论文
共 30 条
[21]  
Ogoshi H., 2000, PORPHYRIN HDB, V6, P279
[22]   Sequential electron-transfer relay in diporphyrin-porphyrin-pyromellitimide triads analogous to that in the photosynthetic reaction center [J].
Osuka, A ;
Nakajima, S ;
Okada, T ;
Taniguchi, S ;
Nozaki, K ;
Ohno, T ;
Yamazaki, I ;
Nishimura, Y ;
Mataga, N .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :92-95
[23]  
Sanders JKM, 2000, PORPHYRIN HDB, V3, P347
[24]   Transition metal-containing rotaxanes and catenanes in motion: Toward molecular machines and motors [J].
Sauvage, JP .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (10) :611-619
[25]   REACTION OF ARYL AND VINYL HALIDES WITH ZEROVALENT NICKEL-PREPARATIVE ASPECTS AND THE SYNTHESIS OF ALNUSONE [J].
SEMMELHACK, MF ;
HELQUIST, P ;
JONES, LD ;
KELLER, L ;
MENDELSON, L ;
RYONO, LS ;
SMITH, JG ;
STAUFFER, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (21) :6460-6471
[26]  
Storm C. B., 1970, J AM CHEM SOC, V92, P1423
[27]   Porphyrin-fullerene host-guest chemistry [J].
Sun, DY ;
Tham, FS ;
Reed, CA ;
Chaker, L ;
Burgess, M ;
Boyd, PDW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10704-10705
[28]   A cyclic dimer of metalloporphyrin forms a highly stable inclusion complex with C60 [J].
Tashiro, K ;
Aida, T ;
Zheng, JY ;
Kinbara, K ;
Saigo, K ;
Sakamoto, S ;
Yamaguchi, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9477-9478
[29]   MECHANISM OF BIARYL SYNTHESIS WITH NICKEL-COMPLEXES [J].
TSOU, TT ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (25) :7547-7560
[30]   REACTIONS OF H-2 (D2) WITH A RHODIUM(II) METALLORADICAL - KINETIC EVIDENCE FOR A 4-CENTERED TRANSITION-STATE [J].
WAYLAND, BB ;
BA, SJ ;
SHERRY, AE .
INORGANIC CHEMISTRY, 1992, 31 (01) :148-150