Thiophene Oligomers: Synthesis and Characterization

Martínez, Francisco; Voelkel, R.; Naegele, D.; Naarmann, H.

doi:10.1080/00268948908037179

Cited by 45 publications

(34 citation statements)

References 21 publications

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“…We may therefore visualize each terthienyl block as being conjugated with a central phenyl ring, resulting in a total of four linear conjugated rings, none of which is conjugated with the others due to the nature of the 1,3,5-positions of the phenyl ring. The conjugation length of compound IIIa must moreover be close to three (2 thienyl rings + phenyl ring), because the wavelength of its absorption maximum (365 nm) lies between the wavelengths of terthiophene (354 nm) [23] and end- …”

Section: Resultsmentioning

confidence: 99%

Star‐Shaped Oligothiophenes for Solution‐Processible Organic Field‐Effect Transistors

Ponomarenko

Kirchmeyer²,

Elschner

et al. 2003

Adv Funct Materials

195

115

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We have designed and successfully synthesized star‐shaped oligothiophenes, which could be used as semiconducting materials for solution‐processible organic field‐effect transistors (FETs). By systematically changing the chemical structure of the star‐shaped oligothiophenes we obtained the structural requirements needed for making working FETs from them. UV‐vis fluorescence measurements showed that a molecule of the star‐shaped compounds under consideration is not a fully conjugated molecule, but it has three independently conjugated oligothienyl‐phenylene blocks. A possible scheme of molecular packing of the star‐shaped oligothiophenes in a lamellar structure was proposed and confirmed by atomic force microscopy (AFM) and X‐ray diffraction (XRD) measurements. Although the star‐shaped semiconductors show a somewhat lower mobility than their linear analogs, they possess better solubility and film‐forming properties, leading to improved spin‐coating processing. The best FETs were made by spin‐coating 1,3,5‐tris(5″‐decyl‐2,2′:5′,2″‐terthien‐5‐yl)benzene from a chloroform solution, which resulted in a mobility of 2 × 10–4 cm2 V –1s–1, a 102 on/off ratio at gate voltages of 0 V and –20 V, and a threshold voltage close to 0 V.

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Section: Resultsmentioning

confidence: 99%

Star‐Shaped Oligothiophenes for Solution‐Processible Organic Field‐Effect Transistors

Ponomarenko

Kirchmeyer²,

Elschner

et al. 2003

Adv Funct Materials

195

115

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“…Fluorad FC 134 was obtained from 3M Company (St. Paul, MN, USA). Tetrahydrohexaoxapentacene (tridioxin, 3DIO ), α ‐sexithiophene ( α ‐6T),25,26 ET3T (Fig. 1) and tetrahydrooctaoxaheptacene ( 4DIO ) were synthesized in our laboratory (manuscripts in preparation).…”

Section: Methodsmentioning

confidence: 99%

Polymer‐assisted laser desorption/ionization analysis of small molecular weight compounds

Woldegiorgis¹,

Kieseritzky²,

Dahlstedt³

et al. 2004

Rapid Comm Mass Spectrometry

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The use of non-polar, small polymers as matrices for the analysis of low molecular weight compounds in polymer-assisted laser desorption/ionization mass spectrometry (PALDI-MS) is demonstrated. The matrices evaluated were either based on an oligothiophene or a benzodioxin backbone. Metallocenes, polycyclic hydrocarbons, a fluorosurfactant, and a subset of small organic compounds with various functionalities, served as model analytes. The mechanism of ionization charge transfer is discussed and ionization potentials for the matrices in the study have been estimated using density functional theory (DFT) calculations. Some of the results are possibly contradictory to the generally accepted limiting conditions for gas-phase charge-transfer reactions. These results are interpreted in the light of energy pooling. Also a new mass calibration procedure for the low-mass region in positive ion mode is presented, and some aspects of the ionization/desorption process leading to radical cations are studied.

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“…No yields are given, but the authors paid very much attention to the purification procedure and the physical constants of the various thiophene oligomers [12]. The use of iodo compounds proved to be even more effective, since H-TI-H 2 was obtained by the nickel-catalyzed coupling [Ni(dppe)C12] of I-T1-H 8 and its Grignard derivative in 90% yield [78].…”

Section: R-mqx + R'-x'mentioning

confidence: 99%

“…With increasing chain length of the oligothiophene the melting point increases as expected. With respect to the electronic properties, the longest wavelength absorptions [ 131, emissions [ 1241 and also the oxidation potentials [12,77] gradually shift to lower energies with increasing number of thiophene rings. This reflects, as expected, an increasing conjugation which is also observed by the colors of the homologous row.…”

Section: Physical Properties Of A-oligothiophenes and Isomersmentioning

confidence: 99%

“…It is almost impossible to predict and control crystal packing at the molecular level [ 1 11 and the rationale behind the idea of covalent linking of the TTFgroups in oligo-TTFs is that this may increase the dimensionality in the solid state. Another aspect of the 'oligomer-approach' is the potential control over the stoichiometry in CT complexes as it has been found [12] that a stoichiometry with two donors to one acceptor does increase the chance of partial electron transfer, which is a prerequisite for metallic conductivity.…”

Section: Redo\-propertiesmentioning

confidence: 99%

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