Synthesis and characterization of poly(dialkylterthiophene-bithiophene) and poly(dialkylterthiophene-thienothiophene) for organic thin film transistors and organic photovoltaic cells

Jeon, Chan Woo; Kang, So-hee; Yun, Hui‐Jun; An, Tae Kyu; Cha, Hyojung; Park, Chan-Eon; Kim, Yun‐Hi

doi:10.1016/j.synthmet.2013.10.007

Cited by 7 publications

(2 citation statements)

References 37 publications

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“…Tetrakis(triphenylphosphine)palladium(0) and 3,6-dibromothieno[3,2- b ]thiophene were purchased from TCI (Tokyo, Japan) and used as received. Monomers including 2,5-bis(trimethylstannyl)thiophene (T), 5,5′-bis(trimethylstannyl)-2,2′-bithiophene (2T), 2,5-bis(trimethylstannyl)-thieno[3,2- b ]thiophene (TT), and ( E )-1,2-bis(5 -(trimethylstannyl)thiophen-2-yl)ethene (TVT) were synthesized according to the reported method. The synthetic steps of biaxially thiophene side chain extended thieno[3,2- b ]thiophene-based quarterthiophene (TT2T) monomers are shown in Scheme , and the 1 H NMR spectra are summarized in the Supporting Information (Figures S1).…”

Section: Methodsmentioning

confidence: 99%

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

Chao

et al. 2015

Macromolecules

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Biaxially thiophene side chain extended thieno [3,2b]thiophene (TT2T)-based polymers, PTTT2T, P2TTT2T, PTTTT2T, and PTVTTT2T, were synthesized by Stille coupling polymerization with different conjugated moieties of thiophene (T), bithiophene (2T), thieno[3,2-b]thiophene (TT), and thiophene− vinylene−thiophene (TVT), respectively. The electronic properties of the prepared polymers could be effectively tuned because the variant πconjugated building block affected the backbone conformation and the resulted morphology. The morphology of the thin films characterized by atomic force microscopy and grazing incidence X-ray diffraction showed that P2TTT2T and PTVTTT2T thin films possessed a better molecular packing with a nanofiber structure owing to their coplanar backbone. The average field-effect mobilities of PTTT2T, P2TTT2T, PTTTT2T, and PTVTTT2T were 6.7 × 10 −6 , 0.36, 2.2 × 10 −3 , and 0.64 cm 2 V −1 s −1 (maximum 0.71), respectively, attributed to the coplanarity of polymer skeleton. In addition, the fabricated FET devices showed a high on/off ratio over 10 7 under ambient for over 3 months, suggesting the excellent environmental stability. The above results demonstrated that the biaxially extended fused thiophene based conjugated polymers could serve as a potential candidate for organic electronic device applications.

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Section: Methodsmentioning

confidence: 99%

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

Chao

et al. 2015

Macromolecules

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“…Dihexyl derivates in position 3′,4′ were obtained through a variant of Ni-catalyzed Kumada reaction [ 99 ]. Disubstituted trimers have been achieved also with di-methyl in 4,4″ using Lawesson’s reagent [ 100 ] or in 3,3″ using a Pd-Grignard [ 101 ] or Pd-halogen coupling [ 102 ], di-butyl chains in 3′-4′ either using Ni-Grignard [ 103 , 104 ] or using Pd-Grignard [ 105 , 106 ], di-tert-butyl 3′,4′ using a Zn-Grignard [ 107 ], di-octyl in 3,3″ with Ni-Grignard [ 108 , 109 , 110 , 111 , 112 , 113 , 114 ], Stille [ 115 , 116 ], Suzuki coupling [ 117 ] and halogen substitution [ 118 ], di-decyl in 3′,4′ using a Stille coupling [ 119 ], di-undecyl [ 120 ] dodecyl via Suzuki [ 121 , 122 ] and di-hexadecyl [ 123 ] using metal-Grignard reaction pathways.…”

Section: Trimer Structuresmentioning

confidence: 99%

Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

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Certainly, the success of polythiophenes is due in the first place to their outstanding electronic properties and superior processability. Nevertheless, there are additional reasons that contribute to arouse the scientific interest around these materials. Among these, the large variety of chemical modifications that is possible to perform on the thiophene ring is a precious aspect. In particular, a turning point was marked by the diffusion of synthetic strategies for the preparation of terthiophenes: the vast richness of approaches today available for the easy customization of these structures allows the finetuning of their chemical, physical, and optical properties. Therefore, terthiophene derivatives have become an extremely versatile class of compounds both for direct application or for the preparation of electronic functional polymers. Moreover, their biocompatibility and ease of functionalization make them appealing for biology and medical research, as it testifies to the blossoming of studies in these fields in which they are involved. It is thus with the willingness to guide the reader through all the possibilities offered by these structures that this review elucidates the synthetic methods and describes the full chemical variety of terthiophenes and their derivatives. In the final part, an in-depth presentation of their numerous bioapplications intends to provide a complete picture of the state of the art.

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Effects of Bulk Heterojunction Morphology Control via Thermal Annealing on the Fill Factor of Anthracene-based Polymer Solar Cells

Cha

et al. 2020

Macromol. Res.

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Synthesis and characterization of poly(dialkylterthiophene-bithiophene) and poly(dialkylterthiophene-thienothiophene) for organic thin film transistors and organic photovoltaic cells

Cited by 7 publications

References 37 publications

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

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

Thiophene-Based Trimers and Their Bioapplications: An Overview

Effects of Bulk Heterojunction Morphology Control via Thermal Annealing on the Fill Factor of Anthracene-based Polymer Solar Cells

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