All Conjugated Poly(3-hexylthiophene)-<i>block</i>
-poly(hexyl-3,4-ethylenedioxythiophene) Copolymers

Bhardwaj, Dinesh; Shahjad,; Gupta, Sonal; Yadav, Preeti; Bhargav, Ranoo; Patra, Asit

doi:10.1002/slct.201701999

Cited by 19 publications

(16 citation statements)

References 38 publications

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“…Alkyl-substituted EDOT monomer 2-dodecyl-2H,3H-thieno[3,4-b][1,4]dioxine (EDOT-C12) and alkoxy-substituted monomer 3,4-bis(hexyloxy)thiophene (3,4-BHOT) were synthesized using a modified literature procedure via p -toluenesulfonic acid-catalyzed transetherification [ 47 , 48 ] of 3,4-dimethoxythiophene and the corresponding alcohol ( Scheme 2 ). Monomer EDOT-C12 was synthesized using one equivalent of 1,2-tetradecanediol, and monomer 3,4-BHOT was synthesized using two equivalents of n -hexanol.…”

Section: Methodsmentioning

confidence: 99%

Enabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes

et al. 2021

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Polythiophenes (PTs) constitute a diverse array of promising materials for conducting polymer applications. However, many of the synthetic methods to produce PTs have been optimized only for the prototypical alkyl-substituted example poly(3-hexylthiophene) (P3HT). Improvement of these methods beyond P3HT is key to enabling the widespread application of PTs. In this work, P3HT and two ether-substituted PTs poly(2-dodecyl-2H,3H-thieno[3,4-b][1,4]dioxine) (PEDOT-C12) and poly(3,4-bis(hexyloxy)thiophene) (PBHOT) are synthesized by the FeCl3-initiated oxidative method under different conditions. Polymerization was carried out according to a common literature procedure (“reverse addition”) and a modified method (“standard addition”), which differ by the solvent system and the order of addition of reagents to the reaction mixture. Gel-permeation chromatography (GPC) was performed to determine the impact of the different methods on the molecular weights (Mw) and degree of polymerization (Xw) of the polymers relative to polystyrene standards. The standard addition method produced ether-substituted PTs with higher Mw and Xw than those produced using the reverse addition method for sterically unhindered monomers. For P3HT, the highest Mw and Xw were obtained using the reverse addition method. The results show the oxidation potential of the monomer and solution has the greatest impact on the yield and Xw obtained and should be carefully considered when optimizing the reaction conditions for different monomers.

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Section: Methodsmentioning

confidence: 99%

Enabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes

et al. 2021

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“…However, despite the significant efforts devoted to this area, the conventional synthetic method like transition‐metal catalyzed coupling reactions always has several drawbacks. The Suzuki‐Miyaura, Stille, Kumada, Negishi, Sonogashira and Heck coupling, etc., were being used for the synthesis, where heteroaryl‐halides were coupled with organometallic heteroarenes [7,8] . These methods are associated with various major drawbacks like i) pre‐functionalization of the heteroarenes, which increases the number of steps in a reaction making it more tedious, ii) pre‐activation of C−H bonds by using materials like highly flammable BuLi and iii) generates by‐product materials such as organostannyl, organolithium, organotin, organozinc, organoborane compounds.…”

Section: Introductionmentioning

confidence: 99%

“…The Suzuki-Miyaura, Stille, Kumada, Negishi, Sonogashira and Heck coupling, etc., were being used for the synthesis, where heteroaryl-halides were coupled with organometallic heteroarenes. [7,8] These methods are associated with various major drawbacks like i) pre-functionalization of the heteroarenes, which increases the number of steps in a reaction making it more tedious, ii) pre-activation of CÀ H bonds by using materials like highly flammable BuLi and iii) generates byproduct materials such as organostannyl, organolithium, organotin, organozinc, organoborane compounds. Thus dehydrohalogenation cross-coupling reaction, so called direct CÀ H arylation is a promising method to overcome these problems because this method does not require prior preparation of organometallic monomer and thus, metal content waste is avoided.…”

Section: Introductionmentioning

confidence: 99%

Hole Transport Materials by Direct C‐H Arylation for Organic Solar Cells: Effect of Structure and Conjugation on Electrical, Optical and Computational Properties

Naqvi

Chaudhary²,

Singhal

et al. 2021

ChemistrySelect

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Significant efforts have been devoted to the synthesis of conjugated molecules due to their interesting properties for organic electronic applications, it is surprising that very few studies have been reported on the development of small molecules for hole transport material (HTM) in organic solar cells through direct C−H arylation. In this work, we have studied the reaction conditions used for the facile synthesis of a series of π conjugated small molecules through direct C−H arylation. The reaction condition was optimized by using different solvents, bases and ligands to achieve the maximum possible yield. Ten phenyl(s)‐flanked conjugated small molecules were prepared using the optimized reaction condition and were characterized. Density functional theory was studied on these molecules to understand the structure‐property relationship and predicting the reliable geometry, electronic structure and properties of conjugated systems. Electrical and optical properties were measured by cyclic voltammetry and UV‐vis absorption spectroscopy. Finally, the organic solar cells were fabricated by solution‐processable deposition of these HTM with device geometry of ITO/HTM/PCDTBT:PC70BM/Al and achieved a power conversion efficiency of 2.40 % under ambient conditions. This method has the advantages of using different aromaticity of heterocyclic rings combined with conjugation length and electronegativity of heteroatom(s) to allow fine‐tuning of HOMO level and band gap engineering.

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“…functionalized an ethylenedioxythiophene monomer with a hexyl side chain and used the controlled polymerization technique of Kumada catalyst transfer polymerization (KCTP) to achieve a PEDOT‐C 6 homopolymer. [ 26 ] Nevertheless, they achieved a polymer with low molecular weight of 4 kg mol −1 , indicating that the hexyl side chains did not enhance the solubility of the final polymer sufficiently. We introduced branched side chains to overcome this issue and synthesized a new generation of dibrominated EDOT monomer, to obtain a sufficiently high molecular weight and well‐controlled PEDOT homopolymer soluble in common organic solvents.…”

Section: Introductionmentioning

confidence: 99%

A Solution‐Processable Pristine PEDOT Exhibiting Excellent Conductivity, Charge Carrier Mobility, and Thermal Stability in the Doped State

Schmode

Hochgesang

Goel

et al. 2021

Macro Chemistry & Physics

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PEDOT:PSS [poly(3,4‐ethylenedioxythiophene) polystyrene sulfonate] is a widely used insoluble conducting polymer, which is therefore processed from dispersions. In this work, PEDOT homopolymers (PEDOT‐C6C8 1 and 2) highly soluble in common solvents like toluene, tetrahydrofuran, and chloroform are synthesized with a high control of molecular weight and low dispersity using Kumada catalyst transfer polymerization of a newly synthesized EDOT monomer carrying a branched alkyl substituent. Pristine PEDOT‐C6C8 allows the use in accumulation mode transistors with a high charge carrier mobility of 5 × 10−4 cm2 V−1 s−1. Moreover, these polymers can be doped in a controlled fashion, reaching conductivities of 10−3 S cm−1 at 10 mol% of a dopant, Spiro‐MeOTAD(TFSI)2. The doped state is remarkably stable, retaining 80% of the initial value after annealing under nitrogen at 100 °C and being exposed to ambient atmosphere for up to 12 h. During doping, the hole injection barrier decreases and reaches an impressively low value of 130 meV at only 2.5 mol% dopant loading without loss in carrier mobility; as monitored using ultraviolet photoelectron‐ and impedance spectroscopy. This new design concept leading to highly soluble polymers with well‐controlled molecular weights provides solution‐processable PEDOT dopable in a well‐controlled fashion.

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All Conjugated Poly(3-hexylthiophene)-block -poly(hexyl-3,4-ethylenedioxythiophene) Copolymers

Cited by 19 publications

References 38 publications

Enabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes

Enabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes

Hole Transport Materials by Direct C‐H Arylation for Organic Solar Cells: Effect of Structure and Conjugation on Electrical, Optical and Computational Properties

A Solution‐Processable Pristine PEDOT Exhibiting Excellent Conductivity, Charge Carrier Mobility, and Thermal Stability in the Doped State

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