Exploration of the Stille Coupling Reaction for the Synthesis of Functional Polymers

Bao, Zhenan; Chan, Wai Kin; Liu, Yu

doi:10.1021/ja00155a007

Cited by 310 publications

(247 citation statements)

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“…9 (2002) F-NMR spectroscopy but at a considerably lower reaction rate than CF 3 COOH. The importance of O 2 in the reductive elimination is also observed in the reaction of 2a (run 4) and 2b with HCl (runs [6][7][8]. 2b shows considerable stability in an aqueous solution of 0.3 M HCl under N 2 at room temperature.…”

Section: Resultsmentioning

confidence: 66%

“…7,8 Factors that control the reductive elimination from diorganometallic complexes, [M(Y)(Y )L n ] (M = Ni, Pd; L = neutral ligand such as 2,2 -bipyridyl and tertiary phosphines) have long been investigated. The diaryl nickel complex has been isolated mainly with electron-withdrawing aryl groups that stabilize the Ni-aryl bond.…”

mentioning

confidence: 99%

“…[1][2][3][4] The reductive elimination of Y-Y from [Ni(Y)(Y )L n ] and [Pd(Y)(Y )L n ] (Y, Y = organic group) is considered to be a key step in Ni-and Pdcomplex promoted organic synthesis 1,5,6 and polymer synthesis. 7,8 Factors that control the reductive elimination from diorganometallic complexes, [M(Y)(Y )L n ] (M = Ni, Pd; L = neutral ligand such as 2,2 -bipyridyl and tertiary phosphines) have long been investigated. [1][2][3] […”

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confidence: 99%

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Promotion of Reductive Elimination Reaction of Diorgano(2,2′-bipyridyl)nickel(II) Complexes by Electron-Accepting Aromatic Compounds, Lewis Acids, and Brønsted Acids.

Yamamoto

Abla

Murakami

2002

Bulletin of the Chemical Society of Japan

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Reductive elimination of R-R from dialkyl(2,2 -bipyridyl)nickel( ), [NiR 2 (bpy)] 1 (R = CH 3 ( 1a ), C 2 H 5 ( 1b ), n -C 3 H 7 ( 1c )), caused by π -coordination of electron-accepting aromatic compounds and reductive elimination of Ar-Ar from [NiAr 2 (bpy)] 2 (Ar = C 6 F 5 ( 2a ) and pyrazolyls ( 2b and 2c )) promoted by electron-accepting aromatic compounds, Lewis acids, and Brønsted acids have been investigated. 1 H-NMR and kinetic data indicate that π -coordination of the electron-accepting aromatic compound to [NiR 2 (bpy)] leads to the reductive elimination of R-R. The rate of the reductive elimination obeys the second-order rate law,Plots of log k vs Σ σ p of the electron-accepting aromatic compound give a line with a slope of 1.8. Brønsted acids cause reductive elimination of Ar-Ar from 2 selectively under several reaction conditions (e.g., 2a with CF 3 COOH in air and 2b with HBr). The reductive elimination reaction of 2a caused by CF 3 COOH obeys the second-order rate law, − 1 at 300.5 K. UV-vis data give information about the electronic states of 2 and the 2b -Brønsted acid adduct. Poly(6-hexylpyridine-2,5-diyl) with a higher molecular weight has been prepared according to the basic information.Reductive elimination is one of the most fundamental reactions in organometallic chemistry.1-4 The reductive elimina-is considered to be a key step in Ni-and Pdcomplex promoted organic synthesis 1,5,6 and polymer synthesis. 7,8 Factors that control the reductive elimination from diorganometallic complexes, [M(Y)(Y )L n ] (M = Ni, Pd; L = neutral ligand such as 2,2 -bipyridyl and tertiary phosphines) have long been investigated. The diaryl nickel complex has been isolated mainly with electron-withdrawing aryl groups that stabilize the Ni-aryl bond.In this paper, we report details of (i) the reductive elimination reaction of [Ni(alkyl) 2 (bpy)] (bpy = 2,2 -bipyridyl) accelerated by the coordination of electron-accepting aromatic compounds such as m-and p-C 6 H 4 (CN) 2 and (ii) the reductive elimination reaction of [Ni(aryl) 2 (bpy)] induced by Lewis acid and protic acids. The Brønsted acids usually induce the cleavage of metal-organic (M-Y) bonds to liberate Y-H compounds; 1,3c,9f,10 however, the present investigation reveals that it can cause selective reductive elimination when the organic group is the electron-accepting aryl group.(2) Analysis of these reductive elimination reactions is expected to improve our understanding of the nickel-complex-promoted synthetic reactions. A part of these results have been published in a communication form. 9c have been determined by X-ray crystallography; they take a square planar structure around Ni, as previously reported for 2c. The molecular structure of 2a is shown in Figure 1 and that of 2b is given in the supporting data.Reductive

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Section: Resultsmentioning

confidence: 66%

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confidence: 99%

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confidence: 99%

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Promotion of Reductive Elimination Reaction of Diorgano(2,2′-bipyridyl)nickel(II) Complexes by Electron-Accepting Aromatic Compounds, Lewis Acids, and Brønsted Acids.

Yamamoto

Abla

Murakami

2002

Bulletin of the Chemical Society of Japan

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“…51,52 Yu et al developed BDT-based PTB1-7 polymers using the Stille coupling of alkoxy-substituted BDTs and ester-substituted TTs, which promoted the quinoid population and effectively reduced the band gap of the conjugated polymers. 1,2,4,21 The solubility of the polymers were greatly enhanced using branched alkyl side chains, and as a result, PTB2-7 exhibited better solubility in common organic solvents compared to PTB1 bearing linear alkyl side chains.…”

Section: Synthetic Strategy: Ingredients For High-perform-ance Polymersmentioning

confidence: 99%

Incremental optimization in donor polymers for bulk heterojunction organic solar cells exhibiting high performance

Mayukh

Jung

et al. 2012

J Polym Sci B Polym Phys

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The power conversion efficiency of an organic solar cell has now exceeded the 10% mark, which is a significant improvement in the last decade. This has been made possible due to the development of low-band-gap polymers with tunable electron affinity, ionization potential, solubility, and miscibility with the fullerene acceptor, and the improved understanding of the factors affecting the critical device parameters such as the V OC and the J SC . This review examines the latest strategies, results, and trends that have evolved in the design of solar cells with better efficiency and durability.

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“…between 5 and 5,5 0 -bistrimethylstannyl-2,2 0 -bithiophene in THF, in the presence of palladium as a catalyst, were carried out through Still polycondensation reaction, 52 giving the polymers P5 and P6, respectively. Both the polymers were fusible and soluble in organic solvents such as THF, toluene, and CHCl 3 .…”

Section: Synthesis and Characterization Of Polymersmentioning

confidence: 99%

Advances in liquid crystalline conjugated polymers

Akagi

2009

J. Polym. Sci. A Polym. Chem.

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ABSTRACT:We review advances in liquid crystalline (LC) conjugated polymers by focusing on (i) ferroelectric and (ii) photoresponsive LC conjugated polymers. In Part 1, LC polyphenylene derivatives were synthesized through substitution of fluorine-containing chiral LC groups into side chains. Poly (para-phenylene) [P1] and poly (meta-phenylene) [P2] derivatives showed chiral smectic C phases responsible for ferroelectricity. They exhibited quick response to electric field, giving switching times of \1 s between two bistable states. The spontaneous polarization (P S ) of P2 remained unchanged even after the electric field became zero, affording the residual polarization (P R ) whose value was the same as that of P S . This indicates that P2 has a potential memory function based on FLC nature. In Part 2, poly (para-phenylenevinylene)[P5] and poly(bithienylene-phenylene) [P6] derivatives were synthesized by introducing dithienylethene moieties into side chains. Drastic quenching of fluorescence occurred when the photoresponsive moiety changed from an open form to a closed one upon an irradiation of ultraviolet light. The quenched fluorescence was recovered through a photoisomerization from the closed form to the open one. Macroscopically aligned P6 film exhibited a linearly polarized fluorescence with significant anisotropy. Reversible quenching and emitting behavior in anisotropic fluorescence was controlled by the photochemical switching.

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Exploration of the Stille Coupling Reaction for the Synthesis of Functional Polymers

Cited by 310 publications

References 0 publications

Promotion of Reductive Elimination Reaction of Diorgano(2,2′-bipyridyl)nickel(II) Complexes by Electron-Accepting Aromatic Compounds, Lewis Acids, and Brønsted Acids.

Promotion of Reductive Elimination Reaction of Diorgano(2,2′-bipyridyl)nickel(II) Complexes by Electron-Accepting Aromatic Compounds, Lewis Acids, and Brønsted Acids.

Incremental optimization in donor polymers for bulk heterojunction organic solar cells exhibiting high performance

Advances in liquid crystalline conjugated polymers

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