Supramolecular design of a porphyrin-[60]fullerene photocurrent generation system on a DNA scaffold fabricated by a conjugate polymer film

Ah Hyun Bae, Tsukasa Hatano, Kazunori Sugiyasu, Takanori Kishida, Masayuki Takeuchi, Seiji Shinkai

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

DNA which binds monocationic [60]fullerene (1) and tetracationic porphyrin (TMPyP) was readily fabricated by electrochemical oxidative polymerization of 3.4-ethylenedioxythiophene (EDOT) and the resultant poly(EDOT) composite was deposited on an ITO electrode as a stable thin film. Spectral and CV analyses established that one 1 and one TMPyP are bound per 57 nucleobase units, that is, every three pitches of DNA. Photoirradiation of this 1/TMPyP/DNA-poly(EDOT) film generated a photocurrent in 3.8% quantum yield, which was much higher than those obtained from 1/DNA and TMPyP/DNA systems. One can conclude, therefore that the photoexcited energy of TMPyP is transferred to 1, which is collected by the electron-conducting poly(EDOT) film. The present paper shows that DNA is useful as a scaffold to arrange redox-active couples in a one-dimensional matrix.

Original languageEnglish
Pages (from-to)3169-3173
Number of pages5
JournalTetrahedron Letters
Volume46
Issue number18
DOIs
Publication statusPublished - May 2 2005

Fingerprint

Porphyrins
Photocurrents
Polymer films
Scaffolds
Polymers
DNA
Quantum yield
Polymerization
Oxidation-Reduction
fullerene C60
Electrodes
Electrons
Thin films
Composite materials

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Supramolecular design of a porphyrin-[60]fullerene photocurrent generation system on a DNA scaffold fabricated by a conjugate polymer film. / Bae, Ah Hyun; Hatano, Tsukasa; Sugiyasu, Kazunori; Kishida, Takanori; Takeuchi, Masayuki; Shinkai, Seiji.

In: Tetrahedron Letters, Vol. 46, No. 18, 02.05.2005, p. 3169-3173.

Research output: Contribution to journalArticle

Bae, Ah Hyun ; Hatano, Tsukasa ; Sugiyasu, Kazunori ; Kishida, Takanori ; Takeuchi, Masayuki ; Shinkai, Seiji. / Supramolecular design of a porphyrin-[60]fullerene photocurrent generation system on a DNA scaffold fabricated by a conjugate polymer film. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 18. pp. 3169-3173.
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