Fused Pyrene-Diporphyrins: Shifting Near-Infrared Absorption to 1.5 μm and Beyond

被引:91
作者
Diev, Vyacheslav V. [1 ]
Hanson, Kenneth [1 ]
Zimmerman, Jeramy D. [2 ,3 ]
Forrest, Stephen R. [2 ,3 ]
Thompson, Mark E. [1 ]
机构
[1] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA
[2] Univ Michigan, Dept Elect Engn & Comp Sci, Ann Arbor, MI 48109 USA
[3] Univ Michigan, Dept Phys, Ann Arbor, MI 48109 USA
关键词
fused-ring systems; dyes/pigments; organic electronics; porphyrinoids; noncovalent interactions; EXCITATION-ENERGY TRANSFER; PORPHYRIN ARRAYS; MESO-MESO; OPTICAL-PROPERTIES; CROSS-SECTION; IR ABSORPTION; TAPES; BETA; ANTHRACENE; COMPLEXES;
D O I
10.1002/anie.201002669
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Sticking together: Direct fusion of pyrene rings with diporphyrins can be achieved without prior activation of aromatic rings. This simple method gives pyrene-diporphyrin hybrids (see picture, C (pyrene) red, C (porphyrin) dark blue, N light blue, Zn green) with a high near-infrared (NIR) absorption that reaches the wavelengths required for use in telecommunications. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5523 / 5526
页数:4
相关论文
共 32 条
[1]   Efficient excitation energy transfer in long meso-meso linked Zn(II) porphyrin Arrays bearing a 5,15-bisphenylethynylated Zn(II) porphyrin acceptor [J].
Aratani, N ;
Cho, HS ;
Ahn, TK ;
Cho, S ;
Kim, D ;
Sumi, H ;
Osuka, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9668-9681
[2]  
BONIFAZI D, 2004, ANGEW CHEM, V116, P4863
[3]   Triply fused ZnII-porphyrin oligomers:: Synthesis, properties, and supramolecular interactions with single-walled carbon nanotubes (SWNTs) [J].
Cheng, Fuyong ;
Zhang, Sheng ;
Adronov, Alex ;
Echegoyen, Luis ;
Diederich, Francois .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (23) :6062-6070
[4]   Expanding the porphyrin π-system by fusion with anthracene [J].
Davis, Nicola K. S. ;
Pawlicki, Milosz ;
Anderson, Harry L. .
ORGANIC LETTERS, 2008, 10 (18) :3945-3947
[5]   Bis-Anthracene Fused Porphyrins: Synthesis, Crystal Structure, and Near-IR Absorption [J].
Davis, Nicola K. S. ;
Thompson, Amber L. ;
Anderson, Harry L. .
ORGANIC LETTERS, 2010, 12 (09) :2124-2127
[6]   meso,meso-linked and triply fused diporphyrins with mixed-metal ions:: Synthesis and electrochemical investigations [J].
Fendt, Leslie-Anne ;
Fang, Hongjuan ;
Plonska-Brzezinska, Marta E. ;
Zhang, Sheng ;
Cheng, Fuyong ;
Braun, Christophe ;
Echegoyen, Luis ;
Diederich, Francois .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (28) :4659-4673
[7]   Synthesis of Extremely π-Extended Porphyrin Tapes from Hybrid meso-meso Linked Porphyrin Arrays: An Approach Towards the Conjugation Length [J].
Ikeda, Toshiaki ;
Aratani, Naoki ;
Osuka, Atsuhiro .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (08) :1248-1256
[8]   Meso-β Doubly Linked Zn(II) Porphyrin Trimers: Distinct anti-versus-syn Effects on Their Photophysical Properties [J].
Ikeda, Toshiaki ;
Aratani, Naoki ;
Easwaramoorthi, Shanmugam ;
Kim, Dongho ;
Osuka, Atsuhiro .
ORGANIC LETTERS, 2009, 11 (14) :3080-3083
[9]   Large π-Aromatic Molecules as Potential Sensitizers for Highly Efficient Dye-Sensitized Solar Cells [J].
Imahori, Hiroshi ;
Umeyama, Tomokazu ;
Ito, Seigo .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (11) :1809-1818
[10]   Enlarged π-electronic network of a meso-meso, β-β, β-β triply linked dibenzoporphyrin dimer that exhibits a large two-photon absorption cross section [J].
Inokuma, Y ;
Ono, N ;
Uno, H ;
Kim, DY ;
Noh, SB ;
Kim, D ;
Osuka, A .
CHEMICAL COMMUNICATIONS, 2005, (30) :3782-3784