Fused H-shaped tetrathiafulvalene–oligothiophenes as charge transport materials for OFETs and OPVs

Wright, Iain A.; Findlay, Neil J.; Arumugam, Sasikumar; Inigo, Anto R.; Kanibolotsky, Alexander L.; Zassowski, Paweł; Domagała, Wojciech; Skabara, Peter J.

doi:10.1039/c3tc32571g

Cited by 18 publications

(38 citation statements)

References 46 publications

(106 reference statements)

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“…Column chromatography was conducted using SiO 2 (300 mesh) from Fisher Scientific. 1 Please do not adjust margins Please do not adjust margins for simplicity. The polarizing optical microscopy (POM) study was carried out on a Nikon optical polarizing microscope equipped with a Mettler Toledo FP900 hot stage.…”

Section: Methodsmentioning

confidence: 99%

“…The phase composition and purity of the as-prepared samples were analyzed by powder Xray diffraction (XRD) with Cu Kα (λ= 1.54178 Å) incident radiation using a Shimadzu XRD-6000 at 40 kV voltage and 50 mA current. The scanning range and step of XRD pattern were [1,2,5]thiadiazole (1) (1.0 g, 3.05 mmol) and Pd 2 (dba) 3 (0.13 g, 0.15 mmol), tri(o-tolyl) phosphine (0.18 g, 0.60 mmol) was added. The flask was evacuated and back-filled with N 2 three times, and then degassed toluene (70 mL) was injected into the mixture.…”

Section: Methodsmentioning

confidence: 99%

“…After removal of the solvents under the reduced pressure, the product was obtained as red oil (0.49 g, 91%) and used in the next step without any further purification. 1 …”

Section: Synthesis Ofmentioning

confidence: 99%

“…The dark residue was purified by silica gel chromatography, eluting with PE-CH 2 Cl 2 (2:1) to give dark solid (145 mg, 73%). 1 3 (4.6 mg, 0.005 mmol), tri(o-tolyl) phosphine (6.1 mg, 0.02 mmol) was added. The flask was evacuated and backfilled with N 2 three times, and then degassed toluene (40 mL) …”

Section: Synthesis Of Dtfb2tmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8] Recently, solution-processed narrow-band gap oligomers have gained increasing research interest because of their unique advantages, such as simple purification, monodisperse structures, no end-group contaminants, and reduced batch-to-batch variability compared to polymer materials. [9][10][11][12][13][14][15][16][17][18][19][20] The functional oligomers have been widely used in organic electronic devices, such as organic photovoltaics (OPV) and organic field-effect transistors(OFET).…”

Section: Introductionmentioning

confidence: 99%

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Rational design of diketopyrrolopyrrole-based oligomers with deep HOMO level and tunable liquid crystal behavior by modulating the sequence and strength of the donor moiety

et al. 2015

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A family of narrow-band gap π-conjugated oligomers and isomers based on diketopyrrolopyrrole and difluorobenzothiadiazole coupled with oligothiophene or thiazole ring have been successfully synthesized. They exhibited intensive absorption bands (300～900 nm) and deep-lying HOMO energy levels (-5.41～-5.60 eV) due to donor-acceptor interaction and multiple fluorine substituents. The sequence and intensity of electron donor moiety play an important role in determining bulk molecular properties, such as the photophysical properties, the HOMO/LUMO energy levels and mesomorphic properties. Compared with isomer DTFB2T, D2TFBT with two n-hexyl-substituted thiophene as the terminal groups exhibited good liquid crystal behavior with Smectic phase when cooled from 180 o C, and it generated a large area of the liquid-crystalline phase at about 100 o C. However, we did not observe such behaviors in DTFB2T due to the different sequence of moiety.We focus our studies on evaluating how structural variations affect molecular properties in two aspects: (1) variation of ability of terminal electron-donor groups through replacing the two thiophenes by two thiazoles to control the molecular energy levels, optical properties; (2) variation of the length (d, J = 3.6 Hz, 1H, Th-H), 8.11-8.10 (d, J = 3.6 Hz, 1H, Th-H), 7.61-7.60 (d, J = 4.8 Hz, 1H, Th-H), 7.28-7.26 (m, 1H, Th-H), 6.95-6.94 (d, J = 3.6 Hz, 1H, Th-H), 2.94-2.90 (t, J = 7.6 Hz, 2H, CH 2 ), 1.81-1.73 (m, 2H, CH 2 ), 1.44-1.32 (m, 6H, CH 2 ), 0.92-0.89 (t, J = 6.8 Hz, 3H, CH 3 ).

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…After removal of the solvents under the reduced pressure, the product was obtained as red oil (0.49 g, 91%) and used in the next step without any further purification. 1 …”

Section: Synthesis Ofmentioning

confidence: 99%

Section: Synthesis Of Dtfb2tmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Rational design of diketopyrrolopyrrole-based oligomers with deep HOMO level and tunable liquid crystal behavior by modulating the sequence and strength of the donor moiety

et al. 2015

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Tuning Crystal Ordering, Electronic Structure, and Morphology in Organic Semiconductors: Tetrathiafulvalenes as a Model Case

Pfattner

Bromley

Rovira

et al. 2015

Adv Funct Materials

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Tetrathiafulvalenes (TTFs) are an appealing class of organic small molecules giving rise to some of the highest performing active materials reported for organic field effect transistors (OFETs). Because they can be easily chemically modified, TTF‐derivatives are ideal candidates to perform molecule–property correlation studies and, especially, to elucidate the impact of molecular and crystal engineering on device performance. A brief introduction into the state‐of‐the‐art of the field‐effect mobility values achieved with TTF derivatives employing different fabrication techniques is provided. Following, structure–performance relationships are discussed, including polymorphism, a phenomenon which is crucial to control for ensuring device reproducibility. It is also shown that chemical modification of TTFs has a strong influence on the electronic structure of these materials, affecting their stability as well as the nature of the generated charge carriers, leading to devices with p‐channel, n‐channel, or even ambipolar behaviour. TTFs have also shown promise in other applications, such as phototransistors, sensors, or as dopants or components of organic metal charge transfer salts used as source–drain contacts. Overall, TTFs are appealing building blocks in organic electronics, not only because they can be tailored to perform fundamental studies, but also because they offer a wide spectrum of potential applications.

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Lest We Forget–The Importance of Heteroatom Interactions in Heterocyclic Conjugated Systems, from Synthetic Metals to Organic Semiconductors

2023

Self Cite

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The field of synthetic metals was, and remains, highly influential for the development of organic semiconductor materials. Yet, with the passing of time and the rapid development of conjugated materials in recent years, the link between synthetic metals and organic semiconductors is at risk of being forgotten. In this review, we reflect on one of the key concepts developed in synthetic metals – heteroatom interactions. The application of this strategy in recent organic semiconductor materials, small molecules and polymers, is highlighted, with analysis of X‐ray crystal structures and comparisons with model systems used to determine the influence of these non‐covalent short contacts. The case is made that the wide range of effective heteroatom interactions and the high performance that has been achieved in devices from organic solar cells to transistors is testament to the seeds sown by the synthetic metals research community.This article is protected by copyright. All rights reserved

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Fused H-shaped tetrathiafulvalene–oligothiophenes as charge transport materials for OFETs and OPVs

Abstract: Complex multi-redox-active organic semiconductors have been made incorporating tetrathiafulvalene as a fused bridge between oligothiophene chains.

Cited by 18 publications

References 46 publications

Rational design of diketopyrrolopyrrole-based oligomers with deep HOMO level and tunable liquid crystal behavior by modulating the sequence and strength of the donor moiety

Rational design of diketopyrrolopyrrole-based oligomers with deep HOMO level and tunable liquid crystal behavior by modulating the sequence and strength of the donor moiety

Tuning Crystal Ordering, Electronic Structure, and Morphology in Organic Semiconductors: Tetrathiafulvalenes as a Model Case

Lest We Forget–The Importance of Heteroatom Interactions in Heterocyclic Conjugated Systems, from Synthetic Metals to Organic Semiconductors

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