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 | |
| Publication status | Published - 2008 Mar 17 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Octupolar trisporphyrin conjugates exhibiting strong two-photon absorption. / Seo, Ju Won; Jang, So Young; Kim, Dongho; Kim, Hee Joon.
In: Tetrahedron, Vol. 64, No. 12, 17.03.2008, p. 2733-2739.Research output: Contribution to journal › Article
TY - JOUR
T1 - Octupolar trisporphyrin conjugates exhibiting strong two-photon absorption
AU - Seo, Ju Won
AU - Jang, So Young
AU - Kim, Dongho
AU - Kim, Hee Joon
PY - 2008/3/17
Y1 - 2008/3/17
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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U2 - 10.1016/j.tet.2008.01.068
DO - 10.1016/j.tet.2008.01.068
M3 - Article
AN - SCOPUS:39149094588
VL - 64
SP - 2733
EP - 2739
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 12
ER -