Design, synthesis and assembly of new thiophene-based molecular functional units with controlled properties

Bäuerle, Peter; Götz, Günther; Hiller, Markus; Scheib, Stefan; Fischer, Thomas; Segelbacher, U.; Bennati, Marina; Grupp, A.; Mehring, M.; Stoldt, M.; Seidel, Christian; Geiger, F.; Schweiger, H.; Umbach, E.; Schmelzer, M.; Roth, S.; Egelhaaf, Hans‐Joachim; Oelkrug, D.; Emele, Peter; Port, H.

doi:10.1016/0379-6779(93)91201-c

Cited by 43 publications

(18 citation statements)

References 46 publications

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“…The poor solubility might result from the strong intermolecular interactions between the dodecyl groups in the solid state. In fact, a solubility as low as 0.02 g/L was reported for α,ω-didodecyltetrathiophene . In addition, the low solubility of the diacyl compound 18 might also be attributed to the intermolecular quadrupole−quadrupole interactions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Electronic Properties of Aldehyde End-Capped Thiophene Oligomers and Other α,ω-Substituted Sexithiophenes

1996

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A series of α,ω-aldehyde end-capped oligomers of thiophene with three, four, five, six, and eight thiophene units have been synthesized using the palladium-catalyzed Stille's coupling reactions. The UV−vis spectral data indicate that these aldehyde end-capped oligomers have longer conjugation lengths as evidenced by the higher λmax values than the corresponding unsubstituted oligothiophenes. The λmax value increases as the number of thiophene units is increased. The intrinsic conductivity of the solution-cast films of the aldehyde end-capped oligothiophenes is generally higher than that of their corresponding unsubstituted counterparts. Other α,ω-substituted sexithiophenes, such as n-dodecanoyl, tert-butyldimethylsilyl, hydroxymethyl, and [(n-butoxyethoxy)ethoxy]methyl sexithiophenes, have also been synthesized. α,ω-Bis([(n-butoxyethoxy)ethoxy]methyl)sexithiophene has a remarkably high solubility in chloroform (1.8 g/L) and a conductivity (1 × 10-6 S/cm) comparable to the unsubstituted sexithiophene.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Electronic Properties of Aldehyde End-Capped Thiophene Oligomers and Other α,ω-Substituted Sexithiophenes

1996

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“…The polythiophenes also have been functionalized with molecular recognition centers as crown ethers and glucose oxidase for sensor applications, as well as with acceptor−donor functions for information storage. An alternative approach which, at least in part, solves the problem with low solubility and processability of the polythiophenes is to use oligothiophenes H−T n −H (2 < n <12) or “end-capped” analogues as building block for the development of novel materials , The oligothiophenes also have found applications as components in electronic devices, for example, as light emitting diodes , and field-effect transistors, , and the properties of these devices seem comparable to those prepared from their long-chain analogues, the polythiophenes.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of α-Functionalized Terthiophenes on Gold

Liedberg¹,

Yang²,

Engquist³

et al. 1997

J. Phys. Chem. B

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α-Functionalized terthiophenes containing disulfide (−S−T3−H)2 and alkanethiol (HS−(CH2)11−T3−H) anchoring groups have been synthesized for direct immobilization onto gold. Monolayer structures of these compounds are prepared by spontaneous assembly from ethanol solutions on evaporated gold substrates and thoroughly characterized by ellipsometry, contact angle goniometry, infrared and X-ray photoelectron spectroscopy, and cyclic voltammetry. The two molecules coordinate to the gold substrate exclusively via the anchoring groups upon formation of gold−thiolate bonds. The kinetics of monolayer formation vary dramatically for the two compounds. The alkanethiol analogue assembles rapidly, within a few minutes, and forms a densely packed and highly organized monolayer, with the alkyl chains in an almost perfect all-trans conformation and the Cα−Cα axis of the α-T3 units tilted about 14° away from the surface normal. The assembly process is much slower for the disulfide, but an organized monolayer with an average α-T3 chain tilt of about 33° will eventually form when the assembly is allowed to equilibrate with a solution containing the disulfide for at least 1 day. Moreover, the two monolayer assemblies also display a remarkably different electrochemical behavior. The heterogeneous electron-transfer rate at the disulfide-covered gold substrate is almost indistinguishable from that at bare gold, suggesting that the assembly contains a large number of easily accessible defects. An alternative mechanism for explaining the large electron-transfer rate involving electronic coupling via the conjugated π-system of the α-T3 units is also proposed. The electrochemical response is significantly reduced for the HS−(CH2)11−T3−H assembly, but another type of defects, the so-called “shallow defects” originating from sparsely populated areas on the electrode surface, can be identified.

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“…Over the last few years, covalent attachment of different functional groups such as redox groups [5][6][7][8] and molecular-recognizing moieties [9][10][11] results in conducting polymers with enhanced solubility, additional redox properties and molecular recognition.…”

Section: Introductionmentioning

confidence: 99%

Reactive groups on polymer coated electrodes, 12. New conducting carrier materials: polyalkylthiophene functionalized with amino group and its protected forms

Li¹,

Koßmehl²,

Kautek³

et al. 2000

Macromol. Chem. Phys.

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Design, synthesis and assembly of new thiophene-based molecular functional units with controlled properties

Cited by 43 publications

References 46 publications

Synthesis and Electronic Properties of Aldehyde End-Capped Thiophene Oligomers and Other α,ω-Substituted Sexithiophenes

Synthesis and Electronic Properties of Aldehyde End-Capped Thiophene Oligomers and Other α,ω-Substituted Sexithiophenes

Self-Assembly of α-Functionalized Terthiophenes on Gold

Reactive groups on polymer coated electrodes, 12. New conducting carrier materials: polyalkylthiophene functionalized with amino group and its protected forms

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