Controlling Rigidity and Planarity in Conjugated Polymers: Poly(3,4‐ethylenedithioselenophene)

Wijsboom, Yair H.; Patra, Asit; Zade, Sanjio S.; Sheynin, Yana; Li, Mao; Shimon, Linda J. W.; Bendikov, Michael

doi:10.1002/anie.200901231

Cited by 103 publications

(96 citation statements)

References 28 publications

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“…Our computed ground-state bond lengths for PEDOT and PEDOS agree closely with previously published results using other computational methods. 10,13 For the PEDOTe system, no previous simulations results appear to have been published.…”

Section: Resultsmentioning

confidence: 99%

Quantum Molecular Dynamical Calculations of PEDOT 12-Oligomer and its Selenium and Tellurium Derivatives

Mirsakiyeva

Hugosson

Crispin

et al. 2016

Journal of Elec Materi

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We present simulation results, computed with the Car-Parrinello molecular dynamics method, at zero and ambient temperature (300 K) for poly (3,4-ethylenedioxythiophene) [PEDOT] and its selenium and tellurium derivatives PEDOS and PEDOTe, represented as 12-oligomer chains. In particular, we focus on structural parameters such as the dihedral rotation angle distribution, as well as how the charge distribution is affected by temperature. We find that for PEDOT, the dihedral angle distribution shows two distinct local maxima whereas for PEDOS and PEDOTe, the distributions only have one clear maximum. The twisting stiffness at ambient temperature appears to be larger the lighter the heteroatom (S, Se, Te) is, in contrast to the case at 0 K. As regards point charge distributions, they suggest that aromaticity increases with temperature, and also that aromaticity becomes more pronounced the lighter the heteroatom is, both at 0 K and ambient temperature. Our results agree well with previous results, where available. The bond lengths are consistent with substantial aromatic character both at 0 K and at ambient temperature. Our calculations also reproduce the expected trend of diminishing gap between the highest occupied molecular orbital and the lowest unoccupied molecular orbital with increasing atomic number of the heteroatom.

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Section: Resultsmentioning

confidence: 99%

Quantum Molecular Dynamical Calculations of PEDOT 12-Oligomer and its Selenium and Tellurium Derivatives

Mirsakiyeva

Hugosson

Crispin

et al. 2016

Journal of Elec Materi

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“…Because the lone pair of electrons of selenium atoms are easily mobile, predominantly quinoidal structures of selenophenes rather than aromatic structures are produced. 51,52 Thus, the incorporation of selenophene into terpolymers could improve the intermolecular interactions and molecular ordered structures of the terpolymers, which was clearly observed by differential scanning calorimetry (DSC) and grazing incidence X-ray scattering (GIXS) measurements. We achieved control of the crystallinity of DPP-based polymers via the random terpolymer approach by using a third component of selenophene that had only one atom different from the thiophene unit of the parent polymers, thereby producing only minimal influence on the other properties of the polymer.…”

Section: Introductionmentioning

confidence: 95%

Determining Optimal Crystallinity of Diketopyrrolopyrrole-Based Terpolymers for Highly Efficient Polymer Solar Cells and Transistors

et al. 2014

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A new series of conjugated random terpolymers (PDPP2T-Se-Th) was synthesized from electron-deficient diketopyrrolopyrrole (DPP) based unit in conjugation with two electronrich selenophene (Se) and thiophene (Th) species, with a view to inducing different crystalline behaviors of the polymers. The crystallinity of the polymers can be systematically controlled by tuning the ratio between Se and Th; an increase in Se content induced a remarkable increase in the melting and crystallization temperatures as well as the crystallinity of the PDPP2T-Se-Th terpolymers. These changes in the crystalline properties of polymers had a dramatic effect on the performances of organic field-effect transistors (OFETs) and polymer solar cells (PSCs). However, their effect on each type of devices was very different.The charge carrier mobilities of the PDPP2T-Se-Th terpolymers in OFET devices increased remarkably as the Se content increased in the polymers, showing that PDPP2T-Se100 with Se/Th ratio= 100/0 had very high hole and electron mobilities (4.72 and 5.54 cm 2 V -1 s -1 , respectively) with well-balanced ambipolar property. In contrast, the best power conversion efficiency (PCE) of 7.2% was observed for the PDPP2T-Se10-Th90 polymers that had Se/Th ratio of 10/90 due to the synergistic contributions from high charge mobility and optimized bulk-heterojunction (BHJ) morphology with fullerene acceptors. Therefore, the Se units in the polymer backbone could serve to (1) enhance charge carrier mobility and (2) optimize BHJ morphology, both of which affect the performance of the PSCs. To understand the effects of the crystallinity of random terpolymers on their performances in OTFTs and PSCs, we systematically investigated the effects of the Se/Th compositions on their optical, electrical, and structural properties.

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“…In situ electropolymerization provides access to uniform polymeric films on conductive substrates with tunable morphologies and thicknesses [271]. However, over the past few decades, electropolymerization has been limited to applications such as electrochromism and conductive films where ion-doping is required [272][273][274][275][276]. Indeed, non-quantitative unlimited electrochemical coupling reactions usually lead to conducting conjugated polymers with high doping states.…”

Section: Carbazole Covalent Coupling and Ecc-lblmentioning

confidence: 99%

Electrochemical nanoarchitectonics and layer-by-layer assembly: From basics to future

et al. 2015

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No. of Pages 30 2 G. Rydzek et al. SummaryDuring the last few decades, electrochemistry and electrode modification have seen a tremendous fall off in creativity with the emergence of the nanoarchitectonic-based layerby-layer (LbL) film deposition technique. An unprecedented variety of building blocks can be immobilized on surfaces, leading to progress in several fields including sensing, electrochromic, electro-responsive and energy devices. This review describes the state of the art of electrochemical devices based on LbL assemblies, with a focus on supercapacitors, biosensors, and electroresponsive LbL such as electrodissolution/electroswelling of coatings. Recently, electrochemistry has also been used as an ''active trigger'' to induce the formation of films by covalent coupling, leading to new nanoarchitectonic approaches beyond the LbL strategy. These emerging electro-coupling reactions, including electroclick and carbazole chemistry, open new perspectives toward architecture and patterning of functional films and are extensively reviewed.

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Controlling Rigidity and Planarity in Conjugated Polymers: Poly(3,4‐ethylenedithioselenophene)

Cited by 103 publications

References 28 publications

Quantum Molecular Dynamical Calculations of PEDOT 12-Oligomer and its Selenium and Tellurium Derivatives

Quantum Molecular Dynamical Calculations of PEDOT 12-Oligomer and its Selenium and Tellurium Derivatives

Determining Optimal Crystallinity of Diketopyrrolopyrrole-Based Terpolymers for Highly Efficient Polymer Solar Cells and Transistors

Electrochemical nanoarchitectonics and layer-by-layer assembly: From basics to future

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