Recent developments in the synthesis of regioregular thiophene-based conjugated polymers for electronic and optoelectronic applications using nickel and palladium-based catalytic systems

Bibi, Amna; Siddiqi, Humaira M.; Hassan, Abbas; Öztürk, Turan

doi:10.1039/c9ra09712k

Cited by 57 publications

(44 citation statements)

References 266 publications

(288 reference statements)

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“…In the synthesis of both polymer donor materials and state‐of‐the‐art NFAs, Pd‐based catalytic cross‐coupling reactions are most widely employed, offering mild reaction conditions and allowing a wide range of molecular functionalization. [ 3,5,14–20 ] Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 ) is one of the most frequently used cross‐coupling catalysts, employed in Stille coupling, [ 21 ] Suzuki coupling, [ 22 ] Negishi coupling, [ 23 ] and Songashira coupling reactions. [ 24 ] Purification protocols aim to remove impurities, including the catalyst residuals, but the purification of high molecular weight compounds can be difficult since efficient techniques such as distillation, crystallization, or column chromatography cannot be employed.…”

Section: Introductionmentioning

confidence: 99%

Effect of Palladium‐Tetrakis(Triphenylphosphine) Catalyst Traces on Charge Recombination and Extraction in Non‐Fullerene‐based Organic Solar Cells

Schopp

Брус

Lee

et al. 2021

Adv Funct Materials

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The effect of the cross‐coupling catalyst tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) on the performance of a model organic bulk‐heterojunction solar cell composed of a blend of poly([2,6′‐4,8‐di(5‐ethylhexylthienyl)benzo[1,2‐b;3,3‐b]dithiophene]{3‐fluoro‐2[(2‐ethylhexyl)carbonyl]thieno[3,4‐b]thiophenediyl}) (PTB7‐Th) donor and 3,9‐bis(2‐methylene‐((3‐(1,1‐dicyanomethylene)‐6,7‐difluoro)‐indanone))‐5,5,11,11‐tetrakis(4‐hexylphenyl)‐dithieno[2,3‐d:2′,3′‐d′]‐s‐indaceno[1,2‐b:5,6‐b′]dithiophene (IOTIC‐4F) non‐fullerene acceptor is investigated. The effect of intentional addition of different amounts of Pd(PPh3)4 on morphology, free charge carrier generation, non‐geminate bulk trap‐ and surface trap‐assisted recombination as well as bimolecular recombination and charge extraction is quantified. This work shows that free charge carrier generation is affected significantly, while the impact of Pd(PPh3)4 on non‐geminate recombination processes is limited because the catalyst does not facilitate efficient trap‐assisted recombination. The studied system shows substantial robustness towards the addition of Pd(PPh3)4 in small amounts.

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Section: Introductionmentioning

confidence: 99%

Effect of Palladium‐Tetrakis(Triphenylphosphine) Catalyst Traces on Charge Recombination and Extraction in Non‐Fullerene‐based Organic Solar Cells

Schopp

Брус

Lee

et al. 2021

Adv Funct Materials

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“…This reaction is one of the commonest methods for the synthesis of terthiophene and its derivatives, since it requires mild reaction conditions, is regioselective, and is compatible with many functional groups, including aldehydes, ketones, alcohols, nitriles, and esters [ 10 ]. The synthesis of unsubstituted terthiophene by Stille coupling is performed using 2,5-dibromo- or 2,5-diiodothiophene with organotin derivatives (such as tributhyl(2-thienyl)tin) in presence of the Pd catalyst [ 25 , 26 , 27 , 28 , 29 ]. The reaction is illustrated in Scheme 4 .…”

Section: Synthetic Methodologiesmentioning

confidence: 99%

Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

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Certainly, the success of polythiophenes is due in the first place to their outstanding electronic properties and superior processability. Nevertheless, there are additional reasons that contribute to arouse the scientific interest around these materials. Among these, the large variety of chemical modifications that is possible to perform on the thiophene ring is a precious aspect. In particular, a turning point was marked by the diffusion of synthetic strategies for the preparation of terthiophenes: the vast richness of approaches today available for the easy customization of these structures allows the finetuning of their chemical, physical, and optical properties. Therefore, terthiophene derivatives have become an extremely versatile class of compounds both for direct application or for the preparation of electronic functional polymers. Moreover, their biocompatibility and ease of functionalization make them appealing for biology and medical research, as it testifies to the blossoming of studies in these fields in which they are involved. It is thus with the willingness to guide the reader through all the possibilities offered by these structures that this review elucidates the synthetic methods and describes the full chemical variety of terthiophenes and their derivatives. In the final part, an in-depth presentation of their numerous bioapplications intends to provide a complete picture of the state of the art.

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“…In comparison, the chemically produced CP needs to be sufficiently soluble to either create films or coat on substrates. Soluble CPs can be created using appropriate functionalization, however, oxidative polymerization of functionalized monomers typically results in regioirregular CPs (Figure 1.2b) whose mechanical and electronic properties will differ substantially from their regioregular analogs (Figure 1.2a) [88]. Regioregular polymers can be synthesized via GRIM polymerization due to the controlled nature of the method.…”

Section: Introduction To Conducting Polymersmentioning

confidence: 99%

Biofunctional conducting polymers: synthetic advances, challenges, and perspectives towards their use in implantable bioelectronic devices

Baker

Wagner

et al. 2021

Advances in Physics: X

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Conducting polymers (CPs) are organic semiconductors that have gained popularity in more recent years as components of bioelectronic devices designed to electrically communicate with biological environments. Synergy between the material and biological tissue, both on a structural and functional level, is paramount for the proper performance of an implantable biomedical device. As such, significant progress has been made on understanding the fundamental impact of the molecular and macro structure of CPs on their functional properties such as conductivity and charge mobility. At the same time, the development of a variety of synthetic approaches has yielded a library of CPs with improved mechanical and electronic properties. Specifically, chemical biofunctionalization of CP films has significantly decreased the foreign body response, the main contributor to device failure. Therefore, this review covers the advances and challenges made in the chemical biofunctionalization of CP films for potential implantable devices. This is achieved by covalently attaching the biocompatible or biofunctional group to the CP backbone via a reactive functional group to create a material with physical and electronic properties that better matches biological tissue. A perspective is presented that this synthetic chemistry approach to biofunctionalization is valuable for the integration of CPs into commercial implantable bioelectronic devices.

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Recent developments in the synthesis of regioregular thiophene-based conjugated polymers for electronic and optoelectronic applications using nickel and palladium-based catalytic systems

Abstract: Thiophene-based conjugated polymers are important conjugated polymers due to their exceptional optical and conductive properties, over the past few decades many researchers have designed novel strategies to reach more efficient materials for electronic applications.

Cited by 57 publications

References 266 publications

Effect of Palladium‐Tetrakis(Triphenylphosphine) Catalyst Traces on Charge Recombination and Extraction in Non‐Fullerene‐based Organic Solar Cells

Effect of Palladium‐Tetrakis(Triphenylphosphine) Catalyst Traces on Charge Recombination and Extraction in Non‐Fullerene‐based Organic Solar Cells

Thiophene-Based Trimers and Their Bioapplications: An Overview

Biofunctional conducting polymers: synthetic advances, challenges, and perspectives towards their use in implantable bioelectronic devices

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