Octupolar trisporphyrin conjugates exhibiting strong two-photon absorption

被引：23

作者：

Seo, Ju-Won ^{[3
]}

Jang, So Young ^{[1
,2
]}

Kim, Dongho ^{[1
,2
]}

Kim, Hee-Joon ^{[3
]}

机构：

[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

[2] Yonsei Univ, Ctr Ultrafast Opt Characterist Control, Seoul 120749, South Korea

[3] Kumoh Natl Inst Technol, Dept Appl Chem, Gumi 730701, South Korea

来源：

TETRAHEDRON | 2008年 / 64卷 / 12期

基金：

新加坡国家研究基金会;

关键词：

D O I：

10.1016/j.tet.2008.01.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report octupolar trisporphyrin conjugates, derived from the symmetrical functionalization of a triphenylamine core with three ethynylporphyrin wings, exhibiting largely enhanced two-photon absorption (TPA) compared to the porphyrin monomers. Octupolar trisporphyrin conjugate tris-H2P was synthesized by the Pd(0)-catalyzed Sonogashira cross-coupling reaction of tris(4-iodophenyl)amine with 5,10,15-tri-(p-tolyl)-20-ethynylporphyrin, and fully characterized by various spectroscopic methods and elemental analysis. The optimized geometry of tris-H2P obtained by semi-empirical AM1 calculations reveals that tris-H2P adopts a propeller-shaped structure. Our photophysical studies strongly manifest that the trisporphyrin conjugates are promising octupolar fluorophores with effective pi-conjugation over the porphyrin wings through the octupolar core. The trisporphyrin conjugates exhibit much larger TPA cross-section values in comparison with the monomers; the TPA cross-section sigma((2)) value of tris-ZnP (11,800 GM) exceeds that of mono-ZnP (630 GM) by about 20 times. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2733 / 2739

页数：7

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