Abstract
1,10-Dioxydecamethylene doubly strapped ZnII-porphyrin S1 was prepared and treated with AgPF6 to give meso-meso-linked porphyrin oligomers Sn (n = 2, 3, 4, 6, 8, and 12), which were converted to triply linked porphyrin tapes TSn by meso,meso′-dibromo meso-meso-linked porphyrin arrays BSn and meso,meso′-diphenyl meso-meso-linked porphyrin arrays PSn. The structures of S1 and S2 have been determined by single-crystal X-ray diffraction analysis. Characteristically, Sn exhibit sharp Q(0,0) absorption and fluorescence bands. Low energy Q-band-like absorption bands of TSn are progressively red-shifted with an increase in the number of porphyrins without saturation behavior of conjugation. The double straps suppress π-π stacking to some extent as seen from partial preservation of vibration structures in the Q-band-like bands of TS4 and TS6 and improve the chemical stabilities of longer tapes such as TS8 and TS12.
| Original language | English |
|---|---|
| Pages (from-to) | 3193-3204 |
| Number of pages | 12 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 2006 Jul 10 |
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All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry
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Synthesis of doubly strapped meso-meso-linked porphyrin arrays and triply linked conjugated porphyrin tapes. / Ikeda, Toshiaki; Lintuluoto, Juha M.; Aratani, Naoki; Zin, Seok Yoon; Kim, Dongho; Osuka, Atsuhiro.
In: European Journal of Organic Chemistry, No. 14, 10.07.2006, p. 3193-3204.Research output: Contribution to journal › Article
TY - JOUR
T1 - Synthesis of doubly strapped meso-meso-linked porphyrin arrays and triply linked conjugated porphyrin tapes
AU - Ikeda, Toshiaki
AU - Lintuluoto, Juha M.
AU - Aratani, Naoki
AU - Zin, Seok Yoon
AU - Kim, Dongho
AU - Osuka, Atsuhiro
PY - 2006/7/10
Y1 - 2006/7/10
N2 - 1,10-Dioxydecamethylene doubly strapped ZnII-porphyrin S1 was prepared and treated with AgPF6 to give meso-meso-linked porphyrin oligomers Sn (n = 2, 3, 4, 6, 8, and 12), which were converted to triply linked porphyrin tapes TSn by meso,meso′-dibromo meso-meso-linked porphyrin arrays BSn and meso,meso′-diphenyl meso-meso-linked porphyrin arrays PSn. The structures of S1 and S2 have been determined by single-crystal X-ray diffraction analysis. Characteristically, Sn exhibit sharp Q(0,0) absorption and fluorescence bands. Low energy Q-band-like absorption bands of TSn are progressively red-shifted with an increase in the number of porphyrins without saturation behavior of conjugation. The double straps suppress π-π stacking to some extent as seen from partial preservation of vibration structures in the Q-band-like bands of TS4 and TS6 and improve the chemical stabilities of longer tapes such as TS8 and TS12.
AB - 1,10-Dioxydecamethylene doubly strapped ZnII-porphyrin S1 was prepared and treated with AgPF6 to give meso-meso-linked porphyrin oligomers Sn (n = 2, 3, 4, 6, 8, and 12), which were converted to triply linked porphyrin tapes TSn by meso,meso′-dibromo meso-meso-linked porphyrin arrays BSn and meso,meso′-diphenyl meso-meso-linked porphyrin arrays PSn. The structures of S1 and S2 have been determined by single-crystal X-ray diffraction analysis. Characteristically, Sn exhibit sharp Q(0,0) absorption and fluorescence bands. Low energy Q-band-like absorption bands of TSn are progressively red-shifted with an increase in the number of porphyrins without saturation behavior of conjugation. The double straps suppress π-π stacking to some extent as seen from partial preservation of vibration structures in the Q-band-like bands of TS4 and TS6 and improve the chemical stabilities of longer tapes such as TS8 and TS12.
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U2 - 10.1002/ejoc.200600289
DO - 10.1002/ejoc.200600289
M3 - Article
SP - 3193
EP - 3204
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 14
ER -