Synthesis, Characterization and Properties of Regioregular Polythiophene‐Based Materials

Ewbank, Paul C.; Stefan, Mihaela C.; Sauvé, Geneviève; McCullough, Richard D.

doi:10.1002/9780470745533.ch2

Cited by 17 publications

(11 citation statements)

References 281 publications

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“…In THF, HT-P3HF, and HH-P3HF have very similar maximum absorption peaks at 465 and 458 nm respectively, which are red-shifted from rr -P3HT (450 nm) . Both HT and HH polyfuran exhibit shoulders near 480−490 nm, which result from vibronic coupling . The well-defined absorption peaks of HT-P3HF and HH-P3HF suggest both polymers adopt a planar and rod-like structure in solution.…”

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confidence: 95%

“…For PTs, the energy required to twist the backbone is quite low, and consequently, solubilizing substituents must be incorporated in a controlled manner to obtain solution-processable materials without sacrificing planarity. The preparation of regioregular head-to-tail poly(3-hexylthiophene) ( rr -P3HT) was an important synthetic achievement to this end, producing a material with superior electronic properties compared to its regioirregular analogues …”

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confidence: 99%

“…The preparation of regioregular head-to-tail poly(3hexylthiophene) (rr-P3HT) was an important synthetic achievement to this end, 4 producing a material with superior electronic properties compared to its regioirregular analogues. 5 Additionally, the polycondensation process to synthesize P3HT was determined to proceed by a chain-growth mechanism, 6 affording materials with controllable molecular weights and low dispersities. This controlled process (termed catalyst transfer polycondensation, CTP) provides access to more complex semiconducting architectures as a means to further tune solid-state organization.…”

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confidence: 99%

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Synthesis of Polyfuran and Thiophene-Furan Alternating Copolymers Using Catalyst-Transfer Polycondensation

et al. 2016

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There is intense interest in the rational design of semiconducting materials to improve organic electronics. Furan is a particularly attractive monomer for building biorenewable and biodegradable π-conjugated frameworks. In this report, regioregular head-to-tail and head-to-head poly(3-hexylfuran) were synthesized using chain-growth polycondensation. The resultant polyfurans have relatively low molecular weights but also low dispersities. The head-to-head polyfuran adopted a nearly identical coplanar backbone conformation as its head-to-tail analog in the solid state, as determined by UV–visible spectroscopy and atomic force microscopy. Extensive aggregation of the furan homopolymer during polymerization led to the investigation of an alternating furan-thiophene copolymer, confirming that furyl-based monomers can polymerize in a chain-growth manner. All of the synthesized polymers are sensitive when exposed to both oxygen and light.

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confidence: 95%

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confidence: 99%

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confidence: 99%

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Synthesis of Polyfuran and Thiophene-Furan Alternating Copolymers Using Catalyst-Transfer Polycondensation

et al. 2016

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“…the distribution between thiophene fractions in PTs at the position 2 or 5 (Scheme 4) where two thiophene molecules are linked together, three different regioregular, i.e., head-to-tail, HT, (2,5'), head-to-head, HH, (2,2'), or tail-to-tail, TT, (5,5') dimers are initially formed (Scheme 4) [35].…”

Section: Regioisomerismmentioning

confidence: 99%

Functionalized polythiophenes: Recognition materials for chemosensors and biosensors of superior sensitivity, selectivity, and detectability

Huynh

Sharma

Sosnowska

et al. 2015

Progress in Polymer Science

125

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“…However, the thiophenechemistry is still a matter of interest as some established substitution methods for chemical derivatization are being modified and improved, while novel methods implying sustainable synthetic approaches are being developed [32]. The most common and straightforward scaffold modification is the introduction of electroactive or solubilizing groups in positions 2-5 [33,34]. Some more recent methodologies involve the fusion with other aromatic rings yielding large aromatic π surfaces [35], or even changes to their oxidation state by the oxidation of the sulfur atom or formation of quinoidal structures [36].…”

Section: Introductionmentioning

confidence: 99%

Thiophene-Based Covalent Organic Frameworks: Synthesis, Photophysics and Light-Driven Applications

2021

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Porous crystalline materials, such as covalent organic frameworks (COFs), have emerged as some of the most important materials over the last two decades due to their excellent physicochemical properties such as their large surface area and permanent, accessible porosity. On the other hand, thiophene derivatives are common versatile scaffolds in organic chemistry. Their outstanding electrical properties have boosted their use in different light-driven applications (photocatalysis, organic thin film transistors, photoelectrodes, organic photovoltaics, etc.), attracting much attention in the research community. Despite the great potential of both systems, porous COF materials based on thiophene monomers are scarce due to the inappropriate angle provided by the latter, which hinders its use as the building block of the former. To circumvent this drawback, researchers have engineered a number of thiophene derivatives that can form part of the COFs structure, while keeping their intrinsic properties. Hence, in the present minireview, we will disclose some of the most relevant thiophene-based COFs, highlighting their basic components (building units), spectroscopic properties and potential light-driven applications.

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Synthesis, Characterization and Properties of Regioregular Polythiophene‐Based Materials

Cited by 17 publications

References 281 publications

Synthesis of Polyfuran and Thiophene-Furan Alternating Copolymers Using Catalyst-Transfer Polycondensation

Synthesis of Polyfuran and Thiophene-Furan Alternating Copolymers Using Catalyst-Transfer Polycondensation

Functionalized polythiophenes: Recognition materials for chemosensors and biosensors of superior sensitivity, selectivity, and detectability

Thiophene-Based Covalent Organic Frameworks: Synthesis, Photophysics and Light-Driven Applications

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