Synthesis of [all]‐S,S‐Dioxide Oligothiophenes Using HOF⋅CH3CN

Amir, Eli; Rozen, Shlomo

doi:10.1002/anie.200501681

Cited by 78 publications

(63 citation statements)

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“…249 Amir and Rozen recently developed a new elegant method for the preparation of all-S,S-dioxide oligothiophenes 2.153 by treatment of alkyl-capped oligothiophenes 2.152 with oxygen transfer agent HOF · CH 3 CN, which possesses a truly electrophilic oxygen center. 250 The synthetic route provided high yielding and rapid S,S-dioxide transformations (1-40 min at 0 to -10°C, Scheme 2.27) without formation of regioisomers as previously reported by the Barbarella group. Compared to starting materials and partially oxygenated S,Sdioxides, which showed a single broad absorption band, the corresponding all-S,S-dioxides displayed structured bands due to the rigidification of the π-conjugated backbone.…”

Section: Oligothiophene Ss-dioxidesmentioning

confidence: 72%

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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Section: Oligothiophene Ss-dioxidesmentioning

confidence: 72%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

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“…The chemical synthesis of the studied compounds has been previously published [2]. The data presented in this paper for the oligoenes are those available in the literature [3].…”

Section: Experimental and Theoretical Detailsmentioning

confidence: 99%

Optical Properties of [all]-S,S-Dioxide Oligothiophenes

Oliva¹,

González²,

Casado³

et al. 2009

Port. Electrochim. Acta

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“…[4] reported a class of oligothiophene-S,S-dioxides and their research revealed that the insertion of nonaromatic thiophene-S,S-dioxide (TO) units within the skeleton of conjugated polymers to form donor-acceptor co-polymers/ oligomers is very promising for use as field-effect transistors and other optoelectronic devices. Now, research on TOs is growing rapidly [5] and TO-containing compounds [6][7][8][9][10][11][12] can emit light under UV excitation with frequencies covering the entire visible range (from the UV to the NIR) and display high photoluminescence efficiencies (some even up to 70%). In the last few years, extensive research has been also devoted to incorporation of benzothiophene-S,S-dioxide (BTO) [13][14][15] and dibenzothiophene-S,S-dioxide (DBTO) [16][17][18][19][20][21][22][23][24][25][26][27][28] units into various conjugated polymers.…”

Section: Introductionmentioning

confidence: 99%

Electropolymerization study of benzothiophenes and characterization of novel poly(dibenzothiophene-S,S-dioxide)

2010

Journal of Electroanalytical Chemistry

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Synthesis of [all]‐S,S‐Dioxide Oligothiophenes Using HOF⋅CH₃CN

Cited by 78 publications

References 38 publications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Optical Properties of [all]-S,S-Dioxide Oligothiophenes

Electropolymerization study of benzothiophenes and characterization of novel poly(dibenzothiophene-S,S-dioxide)

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