Preparation and Photoelectrochemical Properties of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes

Hirayama, Daigo; Yamashiro, Takashi; Takimiya, Kazuo; Aso, Yoshio; Otsubo, Tetsuo; Norieda, Hiroyuki; Imahori, Hiroshi; Sakata, Yoshiteru

doi:10.1246/cl.2000.570

Cited by 47 publications

(51 citation statements)

References 12 publications

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“…In contrast, the CVs recorded in the presence of phenazine methosulfate show that the two reversible one-electron reduction steps observed at ca. 0.0 and À0.90 V on a bare gold electrode are not observed on the electropolymerized monolayer of poly (4). This result suggests that the polymerized layer behaves as an insulator in the negative potential region where the polymer is in its neutral state; these blocking properties being consistent with a homogeneous and dense coverage of the electrode surface.…”

Section: Resultsmentioning

confidence: 76%

“…The immobilization of electroactive p-conjugated systems on gold surfaces by formation of self-assembled monolayers (SAMs) [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] has recently become a focus of high interest motivated by their potential applications in the field of functionalized surfaces, [1] sensors, [2] molecular electronics, [3] or molecular heterojunctions for photovoltaic conversion. [4] On the other hand, several groups have reported the use of surface-immobilized electropolymerizable systems as starting point for the deposition of electrogenerated electroactive conducting polymers.…”

Section: Introductionmentioning

confidence: 99%

“…[4] On the other hand, several groups have reported the use of surface-immobilized electropolymerizable systems as starting point for the deposition of electrogenerated electroactive conducting polymers. [5][6][7][8][9][10][11][12] Wrighton and coworkers used pyrrole attached on silicon by a silane group to promote the adhesion of subsequently electropolymerized poly(pyrrole).…”

Section: Introductionmentioning

confidence: 99%

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Electropolymerized Self‐Assembled Monolayers of a 3,4‐Ethylenedioxythiophene‐Thiophene Hybrid System

Oçafrain

Tran

Blanchard

et al. 2008

Adv Funct Materials

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Self‐assembled monolayers (SAMs) of a conjugated bithiophenic system connected to an alkanethiol chain have been deposited on gold surface. The electroactive bithiophenic system involves a 3,4‐ethylenedioxythiophene (EDOT) unit and a thiophene ring on which an alkanethiol is attached at the internal β‐position via a sulfide linkage. The analysis of the structure of the SAMs by IR spectroscopy, ellipsometry, contact angle measurement and X‐ray photoelectron spectroscopy (XPS) provides consistent results indicating compact monolayers in which the alkyl linkers are arranged in an almost vertical fashion while the bithiophenic‐conjugated systems are essentially parallel to the surface. Cyclic voltammetry shows that application of a few potential scans to SAMs immersed in a medium containing only a supporting electrolyte leads to the typical electropolymerization curves while the CV of the electrooxized monolayer exhibits a reversible cyclic voltammogram characteristic of a stable electroactive extended conjugated system. The characterization of the electropolymerized monolayers by IR spectroscopy, ellipsometry, contact angle measurement, and XPS indicates compact monolayers. The analysis of the current voltage characteristics of the monolayers by conducting AFM before and after electrooxidation shows that the enhancement of the effective conjugation resulting from electropolymerization leads to a significant increase of the transport properties.

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Section: Resultsmentioning

confidence: 76%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Electropolymerized Self‐Assembled Monolayers of a 3,4‐Ethylenedioxythiophene‐Thiophene Hybrid System

Oçafrain

Tran

Blanchard

et al. 2008

Adv Funct Materials

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“…72 Later on, the synthesis of [60]fullerene-linked quaterand octithiophene 2.7 (n ) 1, 2) was reported which bore the above-described thiol-functionalized tripod 2.5 (n ) 1, 2), allowing the formation of well-organized SAMs. 73 Photoelectrochemical measurements were performed using the cell structure Au/SAM 2.6 or 2.7/methyl viologen/Pt.…”

Section: Functionalized Linear Oligothiophenesmentioning

confidence: 99%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

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Amaresh Mishra (right) received his Ph.D. degree in 2000 from the Sambalpur University, India, under the coguidance of Prof. G. B. Behera and Prof. R. K. Behera, working on dye-surfactant interactions in microheterogeneous media. He started his postdoctoral research career in 1999 at the University of South Florida, Tampa, and subsequently at the University of Akron, Ohio, working with Prof. G. R. Newkome, where he gained knowledge in the area of supramolecular and dendrimer chemistry. Later, he joined the Tata Institute of Fundamental Research, Mumbai, in 2002 as a Visiting Fellow working with Prof. N. Periasamy, where he was involved in the synthesis and photophysical studies of organic light emitting materials. In 2005, he joined in the group of Prof. Peter Ba ¨uerle, University of Ulm, Germany, as an Alexander von Humboldt Fellow. His present research interests are centered on chemistry of functional oligothiophenes, donor-acceptor-based conjugated dyes, and metal complexes toward applications in solar energy conversion and molecular electronic and photonic devices. Chang-Qi Ma (left) received his bachelor's degree in chemistry from Beijing Normal University in 1998. In 2003 he obtained his Ph.D. degree at the Technical Institute of Physics and Chemistry, Chinese Academy of Sciences in Beijing with Professor B.-W. Zhang. After that he was a postdoctoral research assistant at Heriot-Watt University in Edinburgh, U.K., with Dr. G. Cooke, until he joined the research group of Prof. P. Ba ¨uerle at the University of Ulm in 2004 as an Alexander von Humboldt fellow, where he is currently a research associate. His main research interests focus on the design and synthesis of novel π-conjugated organic materials for the application in organic electronics, e.g. organic solar cells.Peter Ba ¨uerle (center) received his Ph.D. in organic chemistry from University of Stuttgart (Germany, 1985) working with Prof. F. Effenberger. After a postdoctoral year at MIT, Boston, Massachusetts, in the group of Prof. M. S. Wrighton, he carried out independent research at the University of Stuttgart and received his habilitation (1994). After being Professor of Organic Chemistry at the University of Wu ¨rzburg (Germany, 1994-95), he became Director of the Institute for Organic Chemistry II and Advanced Materials at the University of Ulm (Germany, since 1996). Current research interests of the group include development of novel organic semiconducting and conducting materials, in particular, conjugated poly-and oligothiophenes. Synthetic strategies and new reactions for their functionalization, structure-property relationships, self-assembling properties, and applications in electronic devices, in particular organic solar cells, are investigated. Results have been published in about 200 peer-reviewed scientific papers, 3 book chapters, and 7 patents. For his work in the field of plastic electronics he was awarded with the Rene ´Descartes Prize of the European Union (2000). Guest Professorships at the University of Osaka (Japan, 2002), U...

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“…Self-assembled monolayers (SAMs) based on electroactive p-conjugated systems are the subject of high interest on account of their applications in the fields of molecular electronics, [1][2][3][4] organic electronics, [5] photovoltaic conversion, [6][7][8][9] sensors [10,11] and surfaces with magnetic properties. [12] These SAMs are generally formed by chemisorption on a semiconducting or metallic surface of a p-conjugated molecule that bears a fixation group such as thiol, sulfide, thiocyanate, carboxylic/phosphonic acids, or silane directly grafted on the pconjugated system or through an alkyl linker.…”

Section: Introductionmentioning

confidence: 99%

Thiolate Chemistry: A Powerful and Versatile Synthetic Tool for Immobilization/Functionalization of Oligothiophenes on a Gold Surface

Tran

Bricaud

Oçafrain

et al. 2011

Chemistry A European J

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The synthesis and characterization of a series of quaterthiophenes (4Ts) with thiolate groups protected with 2-cyanoethyl (CNE), 2-trimethylsilylethyl (TMSE), and acetyl (Ac) groups are described. Sequential cleavage of these different protecting groups allows for the preparation of 4Ts derivatized with ferrocene and/or alkanethiol chains. The electrochemical behavior of these compounds has been analyzed in solution by cyclic voltammetry (CV). A ferrocene-derivatized dithiol 4T 14 and a dithiol 4T 15 with two TMSE-protected thiolate groups have been immobilized on a gold surface as monolayers that have been characterized by CV, ellipsometry, contact-angle measurement, and X-ray photoelectron spectroscopy (XPS). The results show that molecules 14 and 15 are doubly grafted with a horizontal orientation of the conjugated system relative to the surface. Furthermore, application of the deprotection/alkylation sequence of the remaining protected thiolate groups on a monolayer of 15 allows for efficient post-functionalization.

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Preparation and Photoelectrochemical Properties of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes

Abstract: [60]Fullerene-linked quarter- and octithiophenes with a disulfide anchoring group have been synthesized, and a photovoltaic cell with a gold electrode modified with the octithiophene derivative showed a large photocurrent under illumination of visible light.

Cited by 47 publications

References 12 publications

Electropolymerized Self‐Assembled Monolayers of a 3,4‐Ethylenedioxythiophene‐Thiophene Hybrid System

Electropolymerized Self‐Assembled Monolayers of a 3,4‐Ethylenedioxythiophene‐Thiophene Hybrid System

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Thiolate Chemistry: A Powerful and Versatile Synthetic Tool for Immobilization/Functionalization of Oligothiophenes on a Gold Surface

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