Biaxially Extended Conjugated Polymers with Thieno[3,2-<i>b</i>]thiophene Building Block for High Performance Field-Effect Transistor Applications

Chao, Pei-Yin; Wu, Hung‐Chin; Lu, Chih-Wei; Hong, Chian-Wen; Chen, Wen‐Chang

doi:10.1021/acs.macromol.5b01243

Cited by 16 publications

(6 citation statements)

References 48 publications

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“…Interestingly, the polymer PT4F-1 that has biaxially extended conjugated alkylthienyl side chains delivered the best device performance with a μ h,max of 0.32 cm 2 V –1 s –1 . Mobility enhancement of the CPs by replacing alkyl with alkylthienyl side chains was also observed by us and others previously. − …”

Section: Resultssupporting

confidence: 80%

Direct Arylation Polycondensation of β-Fluorinated Bithiophenes to Polythiophenes: Effect of Side Chains in C–Br Monomers

et al. 2022

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Six polythiophenes (PThs) were synthesized via direct arylation polycondensation (DArP) with β-fluorinated bithiophenes, that is, 4,4′-difluoro-2,2′-bithiophene (2FBT) and 3,3′,4,4′-tetrafluoro-2,2′-bithiophene (4FBT), as the C–H monomers and 5,5′-dibromo-2,2′-bithiophenes DCBT-2Br, DABT-2Br, and DTBT-2Br that carry alkoxycarbonyl, alkyl, and alkylthienyl side chains at 4,4′-positions, respectively, as the C–Br monomers. Both 2FBT and 4FBT are highly reactive for DArP, and high molecular weight PThs with unobservable chain defects were successfully synthesized from 2FBT/DCBT-2Br, 2FBT/DABT-2Br, 2FBT/DTBT-2Br, and 4FBT/DTBT-2Br. However, the DArP of 4FBT with DCBT-2Br and DABT-2Br produced PThs containing C–H/C–H homo-coupling defects along with relatively lower molecular weights. Detailed theoretical analysis suggests that the occurrence of C–Br reduction-provoked C–H/C–H homo-coupling for 4FBT/DCBT-2Br and 4FBT/DABT-2Br monomer pairs originated from the poor selectivity between the cis- and trans-forms of transition states in the concerted metalation–deprotonation (CMD) process is responsible for the formation of structural defects and depressed molecular weights. This research reveals that a C–H monomer with high reactivity and selectivity is not sufficient for the synthesis of well-defined conjugated polymers via DArP, and the structure of the C–Br monomer also has a significant impact on the results of DArP via influencing the catalytic cycles.

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Section: Resultssupporting

confidence: 80%

Direct Arylation Polycondensation of β-Fluorinated Bithiophenes to Polythiophenes: Effect of Side Chains in C–Br Monomers

et al. 2022

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“…The most efficient solution‐processible organic solar cells are based on blends of an electron donating conjugated polymer (p‐type semiconductor) and an n‐type material usually represented by fullerene derivatives or nonfullerene acceptors . Rational design of novel material combinations has enabled bringing the efficiency of single junction organic solar cells from ≈4%, routinely reported for benchmark devices based on poly(3‐hexylthiophene) P3HT blends with the phenyl‐C 61 butyric acid methyl ester (PC 61 BM), to the current >15% efficiency reached for the most advanced systems comprised of low band gap conjugated polymers and nonfullerene acceptors …”

Section: Introductionmentioning

confidence: 99%

What is Killing Organic Photovoltaics: Light‐Induced Crosslinking as a General Degradation Pathway of Organic Conjugated Molecules

Yamilova

Martynov

Brandvold

et al. 2020

Advanced Energy Materials

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In view of a rapid development and increase in efficiency of organic solar cells, reaching their long‐term operational stability represents now one of the main challenges to be addressed on the way toward commercialization of this photovoltaic technology. However, intrinsic degradation pathways occurring in organic solar cells under realistic operational conditions remain poorly understood. The light‐induced dimerization of the fullerene‐based acceptor materials discovered recently is considered to be one of the main causes for burn‐in degradation of organic solar cells. In this work, it is shown that not only the fullerene derivatives but also different types of conjugated polymers and small molecules undergo similar light‐induced crosslinking regardless of their chemical composition and structure. In the case of conjugated polymers, crosslinking of macromolecules leads to a rapid increase in their molecular weight and consequent loss of solubility, which can be revealed in a straightforward way by gel permeation chromatography analysis via a reduction/loss of signal and/or smaller retention times. Results of this work, thus, shift the paradigm of research in the field toward designing a new generation of organic absorbers with enhanced intrinsic photochemical stability in order to reach practically useful operation lifetimes required for successful commercialization of organic photovoltaics.

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“…Conjugated polymers have been considered for stretchable electrodes due to their wide range of applications including organic field-effect transistors (OFETs), − photovoltaics (OPVs), and light-emitting diodes (OLEDs). , However, their high mechanical flexible was limited by the poor elasticity due to their rigid backbone. The improvement on the stretchability of the conjugated films typically through incorporating rubber-like materials into conjugated polymers for stretchable electrodes or circuits. ,, For example, Jeong and co-workers discovered that the blends of polythiophene (P3HT) nanofibers and polystyrene- block -poly(ethylene- co -butylene)- block -polystyrene (SEBS) rubber exhibited a field effect transistor (FET) mobility larger than 2 × 10 –3 cm 2 V –1 s –1 with the strain up to 50%.…”

Section: Introductionmentioning

confidence: 99%

Stretchable Conjugated Rod–Coil Poly(3-hexylthiophene)-block-poly(butyl acrylate) Thin Films for Field Effect Transistor Applications

Wang

Takshima²,

et al. 2017

Macromolecules

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We report the synthesis, morphology, and properties of poly(3-hexylthiophene)-block-poly(butyl acrylate) (P3HT-b-PBA) for stretchable electronics applications, which are consisted of semiconducting P3HT and low glass transistion temperature (T g) PBA blocks. The P3HT-b-PBA thin films self-assembled into fibrillar-like nanostructures and maintained the edge-on oreientation even at a low P3HT composition, based on the results from atomic force microscopy (AFM) and grazing incidence X-ray diffraction (GIXD). By varying the P3HT/PBA ratio, the tensile modulus decreased as the block length of PBA increased, from 0.93 GPa for P3HT to 0.19 GPa for P3HT-b-PBA12k. The field effect transistor (FET) using P3HT-b-PBA as the active layer exhibited a high p-type mobility over 10–2 cm2 V–1 s–1, indicating its good charge transporting ability. Furthermore, the P3HT-b-PBA6k based FET under 100% strain had a high mobility of 2.5 × 10–2 cm2 V–1 s–1 with an on/off ratio of 7.2 × 106, and it maintained over 10–2 cm2 V–1 s–1 for 1000 cycles, suggesting the promising stability and reproducbility. The result demonstrated that the newly designed conjugated rod–coil block copolymers could have potential applications in stretchable electronic devices.

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Biaxially Extended Conjugated Polymers with Thieno[3,2-b]thiophene Building Block for High Performance Field-Effect Transistor Applications

Cited by 16 publications

References 48 publications

Direct Arylation Polycondensation of β-Fluorinated Bithiophenes to Polythiophenes: Effect of Side Chains in C–Br Monomers

Direct Arylation Polycondensation of β-Fluorinated Bithiophenes to Polythiophenes: Effect of Side Chains in C–Br Monomers

What is Killing Organic Photovoltaics: Light‐Induced Crosslinking as a General Degradation Pathway of Organic Conjugated Molecules

Stretchable Conjugated Rod–Coil Poly(3-hexylthiophene)-block-poly(butyl acrylate) Thin Films for Field Effect Transistor Applications

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