Stille polycondensation: a multifaceted approach towards the synthesis of polymers with semiconducting properties

Liang, Zhen; Neshchadin, Andriy; Zhang, Zhen; Zhao, Fu-Gang; Liu, Xunshan; Yu, Luping

doi:10.1039/d3py00815k

Cited by 2 publications

(3 citation statements)

References 137 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One of the most common synthetic methods for donor–acceptor (D–A) polymers is the Stille coupling polycondensation reaction, which is also applicable to polymers based on the acceptor–acceptor (A–A) framework [ 32 , 33 ]. In this polymerization method, organo-distannane and organo-dihalogen compounds are treated as copolymerizing monomers to form long main chain polymers in the presence of a palladium catalyst.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Dye Semiconductors via Coupling Polymerization Catalyzed by Two Catalysts and Application to Transistor

Ren,

Zhang,

Wang

et al. 2023

Molecules

View full text Add to dashboard Cite

Organic dye semiconductors have received increasing attention as the next generation of semiconductors, and one of their potential applications is as a core component of organic transistors. In this study, two novel diketopyrrolopyrrole (DPP) dye core-based materials were designed and separately prepared using Stille coupling reactions under different palladium catalyst conditions. The molecular weights and elemental compositions were tested to demonstrate that both catalysts could be used to successfully prepare materials of this structure, with the main differences being the weight-average molecular weight and the dispersion index. PDPP-2Py-2Tz I with a longer conjugation length exhibited better thermodynamic stability than the counterpart polymer PDPP-2Py-2Tz II. The intrinsic optical properties of the polymers were relatively similar, while the electrochemical tests showed small differences in their energy levels. The polymers obtained with different catalysts displayed similar and moderate electron mobility in transistor devices, while PDPP-2Py-2Tz I possessed a higher switching ratio. Our study provides a comparison of such dye materials under different catalytic conditions and also demonstrates the great potential of dye materials for optoelectronic applications.

show abstract

Section: Resultsmentioning

confidence: 99%

Preparation of Dye Semiconductors via Coupling Polymerization Catalyzed by Two Catalysts and Application to Transistor

Ren,

Zhang,

Wang

et al. 2023

Molecules

View full text Add to dashboard Cite

show abstract

“…17,18 The toxicity of the trialkyltin reagents used to prepare monomers for the widely used Stille reaction is also highly problematic, especially when contemplating preparation on a commercial scale. 19,20 The development of more modern synthetic methods, particularly direct heteroarylation polymerization (DHAP), has significantly improved routes to conjugated polymers. 21−25 DHAP eliminates the need for organometallic intermediates, shortening syntheses and improving atom economy; however, DHAP is still a metal-catalyzed coupling.…”

Section: ■ Introductionmentioning

confidence: 99%

“…This high degree of reliability made them the standard method of synthesizing conjugated polymers for many years . Unfortunately, the reliance on organometallic intermediates is disadvantageous in terms of atom economy, as they necessarily eliminate metal salts as a byproduct of the polymerization; additional synthetic steps are also required to prepare the organometallic reagents in the first place. , The toxicity of the trialkyltin reagents used to prepare monomers for the widely used Stille reaction is also highly problematic, especially when contemplating preparation on a commercial scale. , …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Conjugated Polymers: Comparing the Indophenine Reaction with Traditional Methods

Faleiro Berbigier,

Kelly

2024

ACS Appl. Polym. Mater.

View full text Add to dashboard Cite

Conjugated polymers are an important class of materials whose development underpins many recent advances in organic electronics. Traditionally, these polymers have been synthesized by transition-metal-catalyzed cross-couplings using organometallic reagents (e.g., Stille couplings). Although direct heteroarylation polymerization (DHAP) dispenses with the organometallic intermediates, DHAP is still a metal-catalyzed coupling, requiring both catalyst optimization and purification to remove trace metal contaminants. In contrast, a recent report from our group demonstrated that the indophenine reaction can be used as a metal-free method to prepare conjugated polymers; however, from this initial proof-of-concept study, it was not clear how it compared to other methods of conjugated polymer synthesis. Therefore, in this report, we synthesized the same polymer using three distinctly different approaches: Stille coupling, DHAP, and the indophenine reaction. This allows us to directly compare the three methodologies; we find that each offers distinct trade-offs in terms of atom economy, defects, and molecular weight.

show abstract

Stille polycondensation: a multifaceted approach towards the synthesis of polymers with semiconducting properties

Abstract: Recent years have witnessed the rapid development of numerous organic polymer-based semiconductors for applications in areas ranging from organic electronics to bioimaging and biosensing.

Cited by 2 publications

References 137 publications

Preparation of Dye Semiconductors via Coupling Polymerization Catalyzed by Two Catalysts and Application to Transistor

Preparation of Dye Semiconductors via Coupling Polymerization Catalyzed by Two Catalysts and Application to Transistor

Synthesis of Conjugated Polymers: Comparing the Indophenine Reaction with Traditional Methods

Contact Info

Product

Resources

About