New synthetic method for the polymerization of alkylthiophenes

́vignon, Marc Se; Papillon, Julien P. N.; Schulz, Emmanuelle; Lemaire, Marc

doi:10.1016/s0040-4039(99)01164-8

Cited by 161 publications

(107 citation statements)

References 18 publications

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“…The synthesis of regioregular P3ATs by direct C–H bond activation was first reported in 1999, using 2-halo-3-alkylthiophenes as monomers and Pd(OAc) 2 as the catalyst [52]. Although the molecular weights of these polymers were initially low ( M w ∼ 3 kDa) and with 90% HT regioregularity, the Pd-mediated dehydrohalogenative polymerization of 2-bromo-3-hexylthiophene yielded regioregular P3ATs of higher molecular weight ( M w ∼ 30 kDa) when using the thermally stable bis-palladacycle known as Herrmann’s catalyst [53].…”

Section: Synthesis Of Organic Electronic Materialsmentioning

confidence: 99%

Pd- and Ni-catalyzed cross-coupling reactions in the synthesis of organic electronic materials

Kim

Wei

et al. 2014

Science and Technology of Advanced Materials

128

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Organic molecules and polymers with extended π-conjugation are appealing as advanced electronic materials, and have already found practical applications in thin-film transistors, light emitting diodes, and chemical sensors. Transition metal (TM)-catalyzed cross-coupling methodologies have evolved over the past four decades into one of the most powerful and versatile methods for C–C bond formation, enabling the construction of a diverse and sophisticated range of π-conjugated oligomers and polymers. In this review, we focus our discussion on recent synthetic developments of several important classes of π-conjugated systems using TM-catalyzed cross-coupling reactions, with a perspective on their utility for organic electronic materials.

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Section: Synthesis Of Organic Electronic Materialsmentioning

confidence: 99%

Pd- and Ni-catalyzed cross-coupling reactions in the synthesis of organic electronic materials

Kim

Wei

et al. 2014

Science and Technology of Advanced Materials

128

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“…The procedures described by Miller and Yu [19] and Lemaire and co-workers [20] were used for the iodination and oligomerization, respectively. To a cooled (0 C) and stirred solution of terthiophene 1 [21] Adv.…”

Section: Methodsmentioning

confidence: 99%

Electrochromic Polymer-Dispersed Liquid-Crystal Film: A New Bifunctional Device

et al. 2005

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Polymer‐dispersed liquid crystals (PDLCs) are liquid‐crystal dispersions within a polymer matrix. These films can be changed from an opaque to a transparent state by applying a suitable alternating‐current electric field. PDLCs have attracted the interest of researchers for their applications as light shutters, smart windows, and active displays. For such applications, electrochromic devices, which change color as a result of electrochemical reactions, have also become a recent focus of research. Herein, we report our preliminary results on bifunctional devices based on PDLCs that host electrochromic guest molecules. Such devices allow both an independent and fast switching from a scattering opaque state to a transmissive transparent state owing to liquid‐crystal reorientation and a color change from white (pale yellow) to dark blue, due to either oxidation or reduction of the electrochromic molecules.

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“…[poly(3-alkylthiophene)] oligomers P47a-d (Scheme 23) were prepared in good yields (89-93 %) by direct arylation of the readily accessible 3-alkyl-substituted 2-iodothiophenes [64] under phase-transfer conditions. The reactions took place in the presence of catalytic amounts of palladium acetate, potassium carbonate as the base, and tetrabutylammonium bromide in DMF at 80°C.…”

Section: Direct Arylationmentioning

confidence: 99%

Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

et al. 2014

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Bequeme Routine: Mehrlagige dünne Polymerfilme wurden durch Elektrophorese auf in Agarose immobilisierten Partikeln angeordnet. Anschließendes Entfernen des Kerns führte zu robusten Kapseln mit unterschiedlichen Polymerzusammensetzungen (siehe Fluoreszenzbild). Dieser Ansatz ermöglicht den vielseitigen und routinemäßigen Aufbau von nano‐ und mikroskaligen Kapseln sowie beschichteten Partikeln in sehr wenigen Prozessschritten.

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New synthetic method for the polymerization of alkylthiophenes

Cited by 161 publications

References 18 publications

Pd- and Ni-catalyzed cross-coupling reactions in the synthesis of organic electronic materials

Pd- and Ni-catalyzed cross-coupling reactions in the synthesis of organic electronic materials

Electrochromic Polymer-Dispersed Liquid-Crystal Film: A New Bifunctional Device

Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

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