meso,meso-linked and triply fused diporphyrins with mixed-metal ions:: Synthesis and electrochemical investigations

被引:32
作者
Fendt, Leslie-Anne [1 ]
Fang, Hongjuan
Plonska-Brzezinska, Marta E.
Zhang, Sheng
Cheng, Fuyong
Braun, Christophe
Echegoyen, Luis
Diederich, Francois
机构
[1] ETH Honggerberg, Organ Chem Lab, HCI, CH-8093 Zurich, Switzerland
[2] Clemson Univ, Dept Chem, Clemson, SC 29634 USA
[3] Univ Bialystok, Inst Chem, PL-15399 Bialystok, Poland
关键词
diporphyrins; electrochemistry; UV/Vis spectroscopy; electrostatic interactions; conjugation;
D O I
10.1002/ejoc.200700505
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel series of biaryl-type, meso,meso-linked and planar, triply fused diporphyrin derivatives was prepared and fully characterized together with the corresponding monoporphyrin control compounds. They feature peripheral meso-3-cyanophenyl and meso-3,5-cyanophenyl groups, which have previously been shown to undergo transformation into malonates without perturbation of the porphyrin core and subsequent Bingel addition to fullerene C-60. The tetrapyrrolic metal binding sites in the diporphyrin arrays are either complexed to two Zn-II or Cu-II ions, or, in a mixed coordination, to one Cu-II and one Zn-II ion; alternatively, one or both sites remain unoccupied. The interaction between the differentially metallated porphyrin rings was systematically investigated by UV/Vis spectroscopy and electrochemistry. Cyclic voltammetry and differential pulse voltammetry reveal that electronic communication in the diporphyrin arrays varies strongly with the mode of connection (meso,meso-linked or triply fused), the nature of the bound metal ion, and the number of peripheral cyano groups. The electrochemical HOMO-LUMO gap in both series of diporphyrins is strongly but differentially affected by the choice of the inserted metal ions. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
引用
收藏
页码:4659 / 4673
页数:15
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