Synthesis of doubly strapped meso-meso-linked porphyrin arrays and triply linked conjugated porphyrin tapes

Toshiaki Ikeda, Juha M. Lintuluoto, Naoki Aratani, Seok Yoon Zin, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

34 Citations (Scopus)

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 languageEnglish
Pages (from-to)3193-3204
Number of pages12
JournalEuropean Journal of Organic Chemistry
Issue number14
DOIs
Publication statusPublished - 2006 Jul 10

Fingerprint

Porphyrins
porphyrins
Tapes
tapes
synthesis
straps
absorption spectra
Chemical stability
conjugation
oligomers
Oligomers
X ray diffraction analysis
Absorption spectra
Fluorescence
Single crystals
saturation
vibration
fluorescence
single crystals
diffraction

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Ikeda, Toshiaki ; Lintuluoto, Juha M. ; Aratani, Naoki ; Zin, Seok Yoon ; Kim, Dongho ; Osuka, Atsuhiro. / Synthesis of doubly strapped meso-meso-linked porphyrin arrays and triply linked conjugated porphyrin tapes. In: European Journal of Organic Chemistry. 2006 ; No. 14. pp. 3193-3204.
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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 journalArticle

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