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

doi:10.1016/j.tetlet.2005.03.059

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 journal › Article › peer-review

16 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 language	English
Pages (from-to)	3169-3173
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2005.03.059
Publication status	Published - May 2 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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

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.",

author = "Bae, {Ah Hyun} and Tsukasa Hatano and Kazunori Sugiyasu and Takanori Kishida and Masayuki Takeuchi and Seiji Shinkai",

year = "2005",

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T1 - Supramolecular design of a porphyrin-[60]fullerene photocurrent generation system on a DNA scaffold fabricated by a conjugate polymer film

AU - Bae, Ah Hyun

AU - Hatano, Tsukasa

AU - Sugiyasu, Kazunori

AU - Kishida, Takanori

AU - Takeuchi, Masayuki

AU - Shinkai, Seiji

PY - 2005/5/2

Y1 - 2005/5/2

N2 - 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.

AB - 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.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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

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