Suzuki–Miyaura catalyst-transfer polycondensation with Pd(IPr)(OAc)<sub>2</sub>as the catalyst for the controlled synthesis of polyfluorenes and polythiophenes

Sui, Aiguo; Shi, Xincui; Tian, Hongkun; Geng, Yanhou; Wang, Fosong

doi:10.1039/c4py00917g

Cited by 52 publications

(38 citation statements)

References 57 publications

(74 reference statements)

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“…8 Later on, also other catalytic systems were found to be successful for SCTP of PFs. 61,62,140,141 Besides PFs also PPP 57 and P3AT 65,141,142 were synthesized in a controlled way with SCTP using Pd-catalysts. Recently, a controlled Nicatalyzed SCTP of poly(thiophene)s was performed.…”

Section: Suzuki-miyaura Catalyst Transfer Polymerization (Sctp)mentioning

confidence: 99%

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Advances in the controlled polymerization of conjugated polymers

Verheyen

Leysen

Eede

et al. 2017

Polymer

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This article features recent advances in the synthesis of conjugated polymers via a controlled polymerization. These polymerizations typically rely on transition metal catalyzed cross coupling reactions. The mechanisms of the polymerization protocols are discussed in detail. An overview of all possible protocols and all homopolymers that have been investigated is given. Next, the synthesis of copolymers-random, gradient and block copolymers-is reviewed. Another advantage of a controlled polymerization is the possibility to introduce specific functional groups, either at the beginning of each polymer chain by the use of an external initiator, or at the end of the polymer chain using an endcapper. Finally, topologies different from simple linear polymer chains are discussed. This feature article is complementary to other recent review articles on this topic. 1,2

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Section: Suzuki-miyaura Catalyst Transfer Polymerization (Sctp)mentioning

confidence: 99%

“…Later, SCTP was used to copolymerize PF and P3AT. 141,142 The research group of Kiriy combined KCTP and NCTP, in which P3AT was polymerized via KCTP and PDTS via NCTP (Scheme 10). 113…”

Section: All-conjugated Block Copolymers With Different Aromatic Moiementioning

confidence: 99%

Advances in the controlled polymerization of conjugated polymers

Verheyen

Leysen

Eede

et al. 2017

Polymer

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“…Relatively high M n and narrow Ð polymers, accompanied by a roughly linear relationship between the feed ratio and M n of the polymers as well as almost constant Ð , were observed in the polymerization initiated by Pd4–Pd6 , indicating that the polymerization occurred via a chain‐growth mechanism rather than a step‐growth mechanism. In addition, it is important to note that Ð around 1.60 is rather broad compared with the polymerization carried out at 0 °C . However, the value is reasonable for the polymerization at room temperature, which in the meantime implies that a slow initiation process takes place because the dimeric structure has to be converted into three‐coordinated initiator with a vacant coordination site for these complexes …”

Section: Resultsmentioning

confidence: 94%

Excellent Control of Perylene Diimide End Group in Polyfluorene via Suzuki Catalyst Transfer Polymerization

Sun

Zhang

Yang

et al. 2016

Macro Chemistry & Physics

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Six aryl Pd(II) bromide complexes based on perylene diimide derivative (Ar) and phosphine mixed‐ligands are successfully synthesized by directly oxidative addition of Ar–Br to the Pd(0) precursor. These complexes with the general formulas ArPdBr(PCy3)2 (PCy3 = tricyclohexylphosphine; Pd1–Pd3) and [ArPdBr(TXP‐2,4)]2 (TXP‐2,4 = tri‐2,4‐xylylphosphine; Pd4–Pd6) are stable and can be handled in air at room temperature. By employing the Pd(II) complexes as initiators, Suzuki catalyst transfer polymerization (SCTP) of AB‐type fluorene monomer is investigated for preparing polyfluorenes (PFs) with the defined end group. Complexes Pd4–Pd6 with auxiliary TXP‐2,4 ligand can initiate polymerization of AB‐type fluorene monomer at room temperature, while higher polymerization temperature is required for Pd1–Pd3 with alkyl phosphine PCy3. The obtained polymers are analyzed by matrix‐assisted laser desorption ionization‐time‐of‐flight mass spectrometry, which confirms that the Ar group is appended to the terminus of the polymer chain. Moreover, PFs prepared by Pd4–Pd6‐catalyzed SCTP bear precisely the Ar group on one chain end and 4‐tert‐butylphenyl end‐capping group on the opposite end, which indicates that Pd4–Pd6 with the bulky TXP‐2,4 exhibit better catalytic performance in SCTP. Photoluminescence spectra of the obtained polymers show a dual or a blue emission resulting from the difference of the molecular weight.

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“…Organoboron reagents( Suzuki-Miyaura coupling) have become ar eagent of choice due to the functional group tolerance of this reaction, and the environmentally benign, boronic acid byproducts. [37,38,59,[63][64][65][66][67][68] Stille-Migita coupling (X-Ar-SnR 3 )i sp erhaps the mildest coupling methodu sed to date, thougha lso the least reactive for CTP ( Figure 1). [39,69,70] The tin species used in the formation of these monomers and the tin byproducts of the coupling are toxic, which is al imitation of this polymerization strategy.A urylated monomers (X-Ar-AuPtBu 3 )a re a recent addition to the family of controlled polymerizations.…”

Section: Choice Of Functional Groups and Cross-couplingmentioning

confidence: 99%

“…[158] The combination of their strong s-donor character,b ench stability, commercial availability,a nd solubility make them effective catalysts in av ariety of cross couplings. Palladium NHCs have been utilized for CTP of thiophenes, [38,39,67,71,159] fluorenes, [67] and phenylenes.T he most common Pd-NHC used in CTP is the PEPPSI-IPr (pyridine enhanced precatalyst preparation, stabilization, initiation) complex. [160] This particularc atalyst is interesting in that it also features the 3-chloropyridine ligand,a nd computations uggests this ligand can affect the polymerization.…”

Section: N-heterocyclic Carbenesmentioning

confidence: 99%

Diversifying Cross‐Coupling Strategies, Catalysts and Monomers for the Controlled Synthesis of Conjugated Polymers

Baker

Tsai

Noonan

2018

Chemistry A European J

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Chain-growth polymerization of aromatic building blocks (termed catalyst-transfer polycondensation or CTP) has emerged as a powerful method for the controlled synthesis of conjugated polymers. CTP affords semiconducting materials with predictable molecular weights, relatively narrow molar mass distributions and tailored backbone compositions (e.g. blocks, gradients, stars). Homogeneous catalysis utilizing transition metals has played a critical role in the rise of this field and this Minireview is designed to highlight some of the catalysts employed for these polycondensations. Some descriptions of the metal and ancillary ligands are included, along with which catalysts have been used for different aromatic monomers. Cross-coupling strategies are discussed briefly for ease of use. Finally, some potential future directions are described for further evolution of this exciting area.

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Suzuki–Miyaura catalyst-transfer polycondensation with Pd(IPr)(OAc)₂as the catalyst for the controlled synthesis of polyfluorenes and polythiophenes

Cited by 52 publications

References 57 publications

Advances in the controlled polymerization of conjugated polymers

Advances in the controlled polymerization of conjugated polymers

Excellent Control of Perylene Diimide End Group in Polyfluorene via Suzuki Catalyst Transfer Polymerization

Diversifying Cross‐Coupling Strategies, Catalysts and Monomers for the Controlled Synthesis of Conjugated Polymers

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Suzuki–Miyaura catalyst-transfer polycondensation with Pd(IPr)(OAc)2as the catalyst for the controlled synthesis of polyfluorenes and polythiophenes

Cited by 52 publications

References 57 publications

Advances in the controlled polymerization of conjugated polymers

Advances in the controlled polymerization of conjugated polymers

Excellent Control of Perylene Diimide End Group in Polyfluorene via Suzuki Catalyst Transfer Polymerization

Diversifying Cross‐Coupling Strategies, Catalysts and Monomers for the Controlled Synthesis of Conjugated Polymers

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Suzuki–Miyaura catalyst-transfer polycondensation with Pd(IPr)(OAc)₂as the catalyst for the controlled synthesis of polyfluorenes and polythiophenes