Synthesis and characterization of trithienocyclotriyne (TTC) and its tetracobalt complex. The first example of a dehydroannulene containing thiophene rings

Solooki, D.; Bradshaw, J. D.; Tessier, Claire A.; Youngs, Wiley J.

doi:10.1021/om00014a017

Cited by 40 publications

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“…TTC was used as a ligand in the reaction with Co 2 (CO) 8 to give a tetracobalt complex 4.35, in which two of the alkynes of TTC bind to hexacarbonyl dicobalt moieties. 659 An isomer of TTC 4.34, in which the macrocycle is built up from 3,4-substituted thiophene units, was synthesized by the same group with the aim to develop liquid crystalline materials, in particular discotic mesogens. 2,5-Alkynylated 3-ethynyl-4-iodothiophenes were cyclized with the catalytic system Pd 0 /Cu(I) to give colorless cyclotriynes 4.36 in yields up to 25% (Scheme 4.12).…”

Section: Mixed Macrocycles Based On -Substitution In Thiophene Unitsmentioning

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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Section: Mixed Macrocycles Based On -Substitution In Thiophene Unitsmentioning

confidence: 99%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

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“…9 Other routes to thienoannulenes have relied on metal-mediated intermolecular couplings. 10 By virtue of the structure of the starting materials, only C nh -and D nh -symmetric macrocycles are produced. In order to probe the structureproperty relationships among the various structural isomers, it is necessary to introduce the thiophene moieties in a stepwise manner to produce DTAs possessing lower symmetries (C s ), i.e.…”

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confidence: 99%

Synthesis and characterization of dehydrothieno[18]annulenes

Sarkar

Haley

2000

Chem. Commun.

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“…Representative examples are shown in Figure . Although thiophene‐fused dehydroannulene 147 (CCDC: 1205022) was confirmed by X‐ray analysis to be strain free, its derivatives 148 seem to be slightly strained. The X‐ray data (CCDC: 1119562, 148 b ) are not sufficient to discuss the bond angles of the alkynes.…”

Section: Angle‐strained Alkyne‐containing π‐Conjugated Macrocyclesmentioning

confidence: 99%

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Miki

Ohe

2019

Chemistry A European J

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Angle‐strained alkyne‐containing π‐conjugated macrocycles are attractive compounds both in functional materials chemistry and biochemistry. Their interesting reactivity as well as photophysical and supramolecular properties have been revealed in the past three decades. This review highlights the recent advances in angle‐strained alkyne‐containing π‐conjugated macrocycles, especially their synthetic methods, the bond angles of alkynes (∠sp at C≡C−C), and their functions. The theoretical and experimental research on cyclo[n]carbons and para‐cyclophynes consisting of ethynylenes and para‐phenylenes are mainly summarized. Related macrocycles bearing other linkers, such as ortho‐phenylenes, meta‐phenylenes, heteroaromatics, biphenyls, extended aromatics, are also overviewed. Bond angles of strained alkynes in π‐conjugated macrocycles, which are generable, detectable, and isolable, are summarized at the end of this review.

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Synthesis and characterization of trithienocyclotriyne (TTC) and its tetracobalt complex. The first example of a dehydroannulene containing thiophene rings

Cited by 40 publications

References 0 publications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Synthesis and characterization of dehydrothieno[18]annulenes

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

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