The synthesis of 5-alkyl[3,4-c]thienopyrrole-4,6-dione-based polymers using a Pd-catalyzed oxidative C–H/C–H homopolymerization reaction

Zhang, Qiang; Wan, Xiangjian; Lu, Yan; Li, Yandong; Li, Yuefeng; Li, Chenxi; Wu, Hao; Chen, Yongsheng

doi:10.1039/c4cc06284a

Cited by 48 publications

(56 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The yield of the resultant polythiazole dropped to 83%, molecular weight was also low (M n ¼ 8 kDa, PDI ¼ 1.28), while the reaction was carried out in absence of potassium acetate (Entry 12). As mentioned previous work, the acetate was not only as ligand, but also as one of buffer [16].…”

Section: Design and Synthesismentioning

confidence: 96%

“…To our expectations, the palladium catalysed cyclic process may not experience zero valent palladium process. As the article mentioned, [16] Pd(0) may be reduced from Pd(II) by either the ligand as reductant or the active hydrogen atom on the aromatic ring [10]. This would be our next focus of study.…”

Section: Design and Synthesismentioning

confidence: 98%

“…More recently, we developed a direct CeH/CeH coupling polymerization for efficient synthesis of polythiophene system [16]. It is necessary to broaden this methodology for polymerization of thiazole derivatives as new materials with many interesting optical and electrical properties.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Pd-catalysed oxidative C–H/C–H coupling polymerization for polythiazole-based derivatives

Zhang

et al. 2015

Polymer

Self Cite

122

157

View full text Add to dashboard Cite

Section: Design and Synthesismentioning

confidence: 96%

Section: Design and Synthesismentioning

confidence: 98%

See 1 more Smart Citation

Pd-catalysed oxidative C–H/C–H coupling polymerization for polythiazole-based derivatives

Zhang

et al. 2015

Polymer

Self Cite

122

157

View full text Add to dashboard Cite

“…In the case of polymerization via oxidative CH/CH coupling, bromination protocols are avoided altogether, thus further reducing the number of steps necessary to synthesize the polymer. As there is no carbon‐halogen bond to undergo oxidative addition in oxidative CH/CH arylation polymerization, the catalyst is oxidized by means of a copper(II) or silver(I) salt and/or oxygen gas (O 2 ) added to the reaction …”

Section: A Perspective On Cross‐coupling Techniques Used In Conjugatementioning

confidence: 99%

CH Activation as a Shortcut to Conjugated Polymer Synthesis

Blaskovits

Leclerc

2018

Macromol. Rapid Commun.

View full text Add to dashboard Cite

Direct (hetero)arylation polymerization exploits the palladium-catalyzed activation of aromatic CH bonds for the atom-economical synthesis of conjugated polymers for a wide range of applications. This account outlines how direct arylation methodologies overcome many of the limitations of contemporary polymerization techniques at both the research and production scale, and explains how monomer design and reaction conditions must be tailored to ensure high polymer molecular weight, yield, and structural integrity. Current research aims to improve further this reaction's profile as a sustainable methodology while at the same time making it competitive with the Migita-Stille and Miyaura-Suzuki polymerizations both in scope of accessible structures and synthetic efficiency. This feature article charts the recent developments and future directions of CH activation research as it moves toward becoming at once an industrially feasible, environmentally friendly, and synthetically powerful polymerization technique.

show abstract

“…Due to only few literature protocols on oxDAP 40,42,43 , optimization of catalyst loading, atmosphere and oxidant was required ( Table 3).…”

Section: Idt Homopolymers Via Oxidative Direct Arylation Polycondensamentioning

confidence: 99%

Indacenodithiophene Homopolymers via Direct Arylation: Direct Polycondensation versus Polymer Analogous Reaction Pathways

et al. 2019

View full text Add to dashboard Cite

Indacenodithiophene (IDT) based materials are emerging high performance conjugated polymers for use in efficient organic photovoltaics and transistors. However, their preparation generally suffers from long reaction sequences and is often accomplished using disadvantageous Stille couplings. Herein, we present detailed synthesis pathways to IDT homopolymers using C-H activation for all C-C coupling steps. Polyketones are first prepared by direct arylation polycondensation (DAP) in quantitative yield and further cyclized polymer analogously. This protocol is suitable for obtaining structurally well-defined IDT homopolymers, provided that the conditions for cyclization are chosen appropriately and that side reactions are suppressed. Moreover, this polymer analogous pathway gives rise to asymmetric side chain patterns, which allows to fine tune physical properties. Alternatively, IDT homopolymers can be obtained via oxidative direct arylation polycondensation of IDT monomers (oxDAP), leading to IDT homopolymers with similar properties but at reduced yield. Detailed characterization by NMR, IR, UV-vis and PL spectroscopy, and thermal properties, is used to guide synthesis and to explain varying field-effect transistor hole mobilities in the range of 10 -6 -10 -3 cm 2 /Vs.

show abstract

The synthesis of 5-alkyl[3,4-c]thienopyrrole-4,6-dione-based polymers using a Pd-catalyzed oxidative C–H/C–H homopolymerization reaction

Abstract: A new, simple, mild, atom economical homopolymerization method through Pd-catalyzed oxidative C-H/C-H coupling was developed for the preparation of a series of 5-alkyl[3,4-c]thienopyrrole-4,6-dione-based conjugated polymers.

Cited by 48 publications

References 29 publications

Pd-catalysed oxidative C–H/C–H coupling polymerization for polythiazole-based derivatives

Pd-catalysed oxidative C–H/C–H coupling polymerization for polythiazole-based derivatives

CH Activation as a Shortcut to Conjugated Polymer Synthesis

Indacenodithiophene Homopolymers via Direct Arylation: Direct Polycondensation versus Polymer Analogous Reaction Pathways

Contact Info

Product

Resources

About