Meso-substituted Porphyrin Derivatives via Palladium-Catalyzed Amination Showing Wide Range Visible Absorption: Synthesis and Photophysical Studies

被引:47
作者
Ladomenou, Kalliopi [1 ]
Lazarides, Theodore [1 ]
Panda, Manas K. [1 ]
Charalambidis, Georgios [1 ]
Daphnomili, Dimitra [1 ]
Coutsolelos, Athanassios G. [1 ]
机构
[1] Univ Crete, Dept Chem, Lab Bioinorgan Chem, Iraklion 71003, Greece
关键词
SENSITIZED SOLAR-CELLS; CROSS-COUPLING REACTIONS; PHOTOINDUCED ELECTRON-TRANSFER; SUBSTITUTED PORPHYRINS; EFFICIENT SYNTHESIS; CRYSTAL-STRUCTURES; CHIRAL PORPHYRINS; ZINC PORPHYRIN; FUNCTIONALIZED PORPHYRINS; SELF-ORGANIZATION;
D O I
10.1021/ic300714n
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In recent years, there has been a growing interest in the design and synthesis of chromophores, which absorb in a wide region of the visible spectrum, as these constitute promising candidates for use as sensitizers in various solar energy conversion schemes. In this work, a palladium-catalyzed coupling reaction was employed in the synthesis of molecular triads in which two porphyrin or boron dipyrrin (BDP) chromophores are linked to the meso positions of a central Zn porphyrin (PZn) ring via an amino group. In the resulting conjugates, which strongly absorb over most of the visible region, the electronic properties of the constituent chromophores are largely retained while detailed emission experiments reveal the energy transfer pathways that occur in each triad.
引用
收藏
页码:10548 / 10556
页数:9
相关论文
共 64 条
[1]   COMPLETION AND REFINEMENT OF CRYSTAL-STRUCTURES WITH SIR92 [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, C ;
GUAGLIARDI, A .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1993, 26 (pt 3) :343-350
[2]  
Aratani N, 2000, ANGEW CHEM INT EDIT, V39, P1458, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1458::AID-ANIE1458>3.0.CO
[3]  
2-E
[4]   Discrete Cyclic Porphyrin Arrays as Artificial Light-Harvesting Antenna [J].
Aratani, Naoki ;
Kim, Dongho ;
Osuka, Atsuhiro .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (12) :1922-1934
[5]  
Armarego WLF, 2009, PURIFICATION OF LABORATORY CHEMICALS, 6TH EDITION, P1
[6]   meso-porphyrinylphosphine oxides:: Mono- and bidentate ligands for supramolecular chemistry and the crystal structures of monomeric {[10,20-diphenylporphyrinatonickel(II)-5,15-diyl]-bis-[P(O)Ph2] and polymeric self-coordinated {[10,20-diphenylporphyrinatozinc(II)-5,15-diyl]-bis-[P(O)Ph2]} [J].
Atefi, Farzad ;
McMurtrie, John C. ;
Turner, Peter ;
Duriska, Martin ;
Arnold, Dennis P. .
INORGANIC CHEMISTRY, 2006, 45 (16) :6479-6489
[7]   DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].
BECKE, AD .
PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100
[8]   Palladium-mediated synthesis of novel meso-chiral porphyrins:: cobalt-catalyzed cyclopropanation [J].
Chen, Y ;
Gao, GY ;
Zhang, XP .
TETRAHEDRON LETTERS, 2005, 46 (30) :4965-4969
[9]   Bromoporphyrins as versatile synthons for modular construction of chiral porphyrins: Cobalt-catalyzed highly enantioselective and diastereoselective cyclopropanation [J].
Chen, Y ;
Fields, KB ;
Zhang, XP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) :14718-14719
[10]   Facile and efficient synthesis of meso-arylamino- and alkylamino-substituted porphyrins via palladium-catalyzed amination [J].
Chen, Y ;
Zhang, XP .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4432-4438