Octupolar trisporphyrin conjugates exhibiting strong two-photon absorption

Ju Won Seo; So Young Jang; Dongho Kim; Hee Joon Kim

doi:10.1016/j.tet.2008.01.068

Octupolar trisporphyrin conjugates exhibiting strong two-photon absorption

Ju Won Seo, So Young Jang, Dongho Kim, Hee Joon Kim

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

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 π-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 σ⁽²⁾ value of tris-ZnP (11,800 GM) exceeds that of mono-ZnP (630 GM) by about 20 times.

Original language	English
Pages (from-to)	2733-2739
Number of pages	7
Journal	Tetrahedron
Volume	64
Issue number	12
DOIs	https://doi.org/10.1016/j.tet.2008.01.068
Publication status	Published - 2008 Mar 17

Bibliographical note

Funding Information:
This work was supported by the Korea Research Foundation (KRF-2005-202-C00184). The work at Yonsei University was supported by the Star Faculty Program of the Ministry of Education, Korea for Human Resources. We thank Professor Jin Yong Lee for calculating optimized geometry of tris-H 2 P .

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.01.068

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title = "Octupolar trisporphyrin conjugates exhibiting strong two-photon absorption",

abstract = "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 π-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 σ(2) value of tris-ZnP (11,800 GM) exceeds that of mono-ZnP (630 GM) by about 20 times.",

author = "Seo, {Ju Won} and Jang, {So Young} and Dongho Kim and Kim, {Hee Joon}",

note = "Funding Information: This work was supported by the Korea Research Foundation (KRF-2005-202-C00184). The work at Yonsei University was supported by the Star Faculty Program of the Ministry of Education, Korea for Human Resources. We thank Professor Jin Yong Lee for calculating optimized geometry of tris-H 2 P .",

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AU - Jang, So Young

AU - Kim, Dongho

AU - Kim, Hee Joon

N1 - Funding Information: This work was supported by the Korea Research Foundation (KRF-2005-202-C00184). The work at Yonsei University was supported by the Star Faculty Program of the Ministry of Education, Korea for Human Resources. We thank Professor Jin Yong Lee for calculating optimized geometry of tris-H 2 P .

PY - 2008/3/17

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N2 - 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 π-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 σ(2) value of tris-ZnP (11,800 GM) exceeds that of mono-ZnP (630 GM) by about 20 times.

AB - 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 π-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 σ(2) value of tris-ZnP (11,800 GM) exceeds that of mono-ZnP (630 GM) by about 20 times.

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Octupolar trisporphyrin conjugates exhibiting strong two-photon absorption

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