Facile oxidative rearrangement of dispiro-porphodimethenes to nonplanar and sheetlike porphyrins with intense absorptions in the near-IR region

被引:96
作者
Gill, HS
Harmjanz, M
Santamaría, J
Finger, I
Scott, MJ
机构
[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA
[2] Univ Florida, Ctr Catalysis, Gainesville, FL 32611 USA
[3] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada CSIC, E-33071 Oviedo, Spain
关键词
fused-ring systems; photochemistry; porphyrinoids; rearrangements; redox chemistry;
D O I
10.1002/anie.200352762
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Exceedingly large, planar porphyrin systems composed of 49 non-hydrogen nuclei in highly delocalized it systems display exceptionally low-energy transitions in UV/Vis/NIR spectroscopy and in cyclic voltammetry. The spectra shown are for cis palladium complex depicted and the corresponding trans isomer.
引用
收藏
页码:485 / 490
页数:6
相关论文
共 57 条
[1]  
Aihara H, 2001, ANGEW CHEM INT EDIT, V40, P3439, DOI 10.1002/1521-3773(20010917)40:18<3439::AID-ANIE3439>3.0.CO
[2]  
2-Z
[3]  
AIHARA H, 2001, ANGEW CHEM, V113, P3547
[4]   Molecular structure of Fe(III) 2,3,7,8,12,13,17,18-octaethyl-5,10,15,20-tetraphenylporphyrin perchlorate:: a saddle-shaped porphyrin with an intermediate S=3/2 spin state [J].
Barkigia, KM ;
Renner, MW ;
Fajer, J .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2001, 5 (04) :415-418
[5]   REVERSIBLE INTRAMOLECULAR ELECTRON-TRANSFER WITHIN A RUTHENIUM(III) PORPHYRIN-RUTHENIUM(II) PORPHYRIN PI-CATION RADICAL SYSTEM INDUCED BY CHANGES IN AXIAL LIGATION [J].
BARLEY, MH ;
DOLPHIN, D ;
JAMES, BR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (22) :1499-1500
[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]   The porphyrinogen-porphodimethene relationship leading to novel synthetic methodologies focused on the modification and functionalization of the porphyrinogen and porphodimethene skeletons [J].
Bonomo, L ;
Solari, E ;
Scopelliti, R ;
Floriani, C ;
Re, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (22) :5312-5326
[8]  
BOTULINSKI A, 1982, ADV CHEM SER, P253
[9]  
BUCHLER JW, 1974, LIEBIGS ANN CHEM, P1046
[10]   The rational synthesis of chlorins via rearrangement of porphodimethenes:: Influence of β-substituents on the regioselectivity and stereoselectivity of pyrroline ring formation [J].
Burns, DH ;
Li, YH ;
Shi, DC ;
Caldwell, TM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4536-4546