Synthesis and Characterization of Poly(pyridine vinylene) via the Sulfinyl Precursor Route

Gillissen, Stijn; Jonforsen, Maria; Kesters, Els; Johansson, Björn; Theander, M.; Andersson, Mats R.; Inganäs, Olle; Lutsen, Laurence; Vanderzande, Dirk

doi:10.1021/ma010575w

Cited by 28 publications

(28 citation statements)

References 17 publications

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“…Stille couplings were used to produce HH bis(pyridyl)ethene, which was further condensed with distannylethylene to produce regioregular HH-PPyVs, whereas the polymerization of 5-bromo-2-vinylpyridine using Heck conditions yielded HT-PPyVs (scheme 38). PPyVs have been found to be photoluminescent at 600 nm, with efficiencies of up to 14% [126]. …”

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

129

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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

129

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“…These monomers were previously shown to be polymerizable. [47][48][49] The effect of substituents on the electronic structure was also studied by varying the polarizer group (P).…”

Section: Diradical Character Of the P-quinodimethane Monomersmentioning

confidence: 99%

PPV Polymerization through the Gilch Route: Diradical Character of Monomers

Nikolić

Wouters

Romanova

et al. 2015

Chemistry A European J

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Despite various studies on the polymerization of poly(p-phenylene vinylene) (PPV) through different precursor routes, detailed mechanistic knowledge on the individual reaction steps and intermediates is still incomplete. The present study aims to gain more insight into the radical polymerization of PPV through the Gilch route. The initial steps of the polymerization involve the formation of a p-quinodimethane intermediate, which spontaneously self-initiates through a dimerization process leading to the formation of diradical species; chain propagation ensues on both sides of the diradical or chain termination occurs by the formation of side products, such as [2.2]paracyclophanes. Furthermore, different p-quinodimethane systems were assessed with respect to the size of their aromatic core as well as the presence of heteroatoms in/on the conjugated system. The nature of the aromatic core and the specific substituents alter the electronic structure of the p-quinodimethane monomers, affecting the mechanism of polymerization. The diradical character of the monomers has been investigated with several advanced methodologies, such as spin-projected UHF, CASSCF, CASPT2, and DMRG calculations. It was shown that larger aromatic cores led to a higher diradical character in the monomers, which in turn is proposed to cause rapid initiation.

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“…Since the reaction conditions at elevated temperature employed for p-xylene could not be used, we performed the chlorination of the nitrogen-containing compounds at the reflux temperature of tetrachloromethane using benzoyl peroxide as the radical initiator instead. Although comparable standard conditions have been used for methyl chlorination of 1b and 1c previously, the reported yields for the dichloride 2b were 20% [7], 23% [8] and 29% [9] while in the case of 1c the reaction afforded 70% yield of the monochloride 5c [10].…”

Section: Results and Disscusionmentioning

confidence: 95%

Improved synthesis of bis(chloromethyl)arene monomers

Almassio¹,

Sarimbalis²,

Garay³

2005

Designed Monomers and Polymers

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We report here on the experimental conditions for radical chlorination that provide improved yields of 2,5-bis(chloromethyl) pyridine and pyrazine, as well as on theoretical calculations which were performed in order to gain some insight regarding the factors that affect reactivity in these systems. The difficulties encountered previously in the methyl functionalization of N-heteroarenes are not due to radical selectivity that produces low yield of the dichlorides or to lower reactivity of this type of compounds, but to the post-halogenation reactions that occur on the desired products. Therefore, a careful handling during and after the reaction allowed us to find conditions for product optimization of α, α -dichlorinated monomers.

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Synthesis and Characterization of Poly(pyridine vinylene) via the Sulfinyl Precursor Route

Cited by 28 publications

References 17 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

PPV Polymerization through the Gilch Route: Diradical Character of Monomers

Improved synthesis of bis(chloromethyl)arene monomers

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