Synthesis of Oligothiophene-Bridged Bisporphyrins and Study of the Linkage Dependence of the Electronic Coupling

Odobel, Fabrice; Suresh, S. J.; Blart, Errol; Nicolas, Yohann; Quintard, Jean‐Paul; Janvier, Pascal; Questel, Jean‐Yves Le; Illien, Bertrand; Rondeau, David; Richomme, Pascal; Häupl, Tilmann; Wallin, Staffan; Hammarström, Leif

doi:10.1002/1521-3765(20020703)8:13<3027::aid-chem3027>3.0.co;2-z

Cited by 94 publications

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“…Krebs et al synthesized zinc porphyrin 2.227, which was linked to regioregular octi(3-hexylthiophene) by a Stille-type coupling reaction of a stannyl derivative of the octithiophene and 5,15-dibromo-10,20-bis(3,5-di-tert-butylphenyl)zinc(II)- 321 These compounds demonstrated the influence of the oligothiophene bridge on interporphyrin electronic interactions. The synthesis of the new triads was carried out by Pd 0 -catalyzed cross-coupling reactions of 5-iodo-10,15,20-{3,5-bis(tert-butylphenyl)}porphyrin and the appropriately substituted oligothiophenes.…”

Section: Porphyrin-functionalized Oligothiophenesmentioning

confidence: 82%

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: Porphyrin-functionalized Oligothiophenesmentioning

confidence: 82%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

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“…Small modifications to the procedure for the production and isolation of monobrominated diarylporphyrin were made in [28]. The bromination of the triarylporphyrin in cold chloroform in the presence of pyridine takes place with a yield of 96%, while the same reaction with 1 equiv.…”

Section: Meso-substituted Porphyrinsmentioning

confidence: 99%

Bromination of porphyrins (Review)

Chumakov

Khoroshutin

Anisimov

et al. 2009

Chem Heterocycl Comp

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“…[18] Because of the requirements of conjugation, electronic coupling and minimal steric repulsion, introduction of a triple bond was the first choice for realising the linear spacer concept. [19] A Sonogashira cross-coupling reaction using nickel complex 11 and 2-ethynyl-4-hexoxythiophene 12 gave 13 in 84% yield. [11,12] Isolation of the crude product using column chromatography was difficult.…”

Section: Synthesesmentioning

confidence: 99%

“…Thus, the extent of conjugation is somewhat less in 17, compared to 13, but still much better than in 10 (560 mV gap). Similar observations concerning the extent of electronic coupling were made by Odobel et al [19] who connected two porphyrins by a thiophene bridge. Considering the multisweep experiment and formation of an electroactive product, which can be deduced from increasing currents, the results with 17 were better than with 10.…”

Section: Absorption Spectramentioning

confidence: 99%

A New Synthetic Approach to Thiophene‐Nickel(II)porphyrin Hybrid Molecules and their Electrochemical and Computational Investigation

Zöllner

Frähmcke

Elstner

et al. 2010

Macro Chemistry & Physics

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New synthetic strategies for thiophene‐nickel(II)porphyrin hybrid molecules are described. Three principles—linear direct, linear spacer and lateral spacer connectivities—were realised and compared with respect to their electrochemical behaviour. Computational investigations by DFT methods confirm experimental data and explain cylic voltammetric oxidations. For the linear direct connectivity, the number of thiophene units per substituted position must be at least two, since the porphyrin core acts as conjugation breaker and hinders the formation of higher oligomers. Alternatively an ethynylene spacer can be introduced to increase conjugation and to optimise the conducting properties. The lateral spacer connection mode proved to be best suited to the electrochemical formation of hybrid compounds.magnified image

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Synthesis of Oligothiophene-Bridged Bisporphyrins and Study of the Linkage Dependence of the Electronic Coupling

Cited by 94 publications

References 0 publications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Bromination of porphyrins (Review)

A New Synthetic Approach to Thiophene‐Nickel(II)porphyrin Hybrid Molecules and their Electrochemical and Computational Investigation

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