Design and synthesis of two conjugated semiconductors containing quinoidal cyclopentadithiophene core

Wang, Kai; Li, Zheng; Huang, Jun; Wang, Tingting; Gao, Jiaxin; Gao, Yu; Wang, Shuojun; He, Shuang-Hui; Lv, Aifeng; Wang, Ming

doi:10.1016/j.dyepig.2021.109336

Cited by 7 publications

(4 citation statements)

References 40 publications

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“…The synthesis process of QP1 and QT1 was reported previously, 37 and we have newly obtained QP2 and QT2 in this work using a method reported previously, 38 which is illustrated in Fig. S1 (ESI†).…”

Section: Experimental Synthesis and Measurementsmentioning

confidence: 94%

Excitation localization/delocalization induced intramolecular singlet fission in cyclopentadithiophene-based quinoidal derivatives

Wen,

Zhou,

et al. 2023

Phys. Chem. Chem. Phys.

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Section: Experimental Synthesis and Measurementsmentioning

confidence: 94%

Excitation localization/delocalization induced intramolecular singlet fission in cyclopentadithiophene-based quinoidal derivatives

Wen,

Zhou,

et al. 2023

Phys. Chem. Chem. Phys.

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“…Recently, an example of cyclopentadithiophene (CPDT) unit incorporated as an end group on the quinoidal structures allowing fine-tuning the FMO energy levels of the molecular components was reported by Wang and coworkers [ 33 ]. Even though CPDT is more donating than fluorenyl, the introduction of this group as a terminal part of quinoidal frameworks has noticeable stabilizing effects on the HOMO level, while the LUMO remains almost unaltered.…”

Section: Synthetic Tactics Of π-Extended Quinoidal Acceptorsmentioning

confidence: 99%

Recent Research Progress in Indophenine-Based-Functional Materials: Design, Synthesis, and Optoelectronic Applications

Ren

Yassar

2023

Materials

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This review highlights selected examples, published in the last three to four years, of recent advance in the design, synthesis, properties, and device performance of quinoidal π-conjugated materials. A particular emphasis is placed on emerging materials, such as indophenine dyes that have the potential to enable high-performance devices. We specifically discuss the recent advances and design guidelines of π-conjugated quinoidal molecules from a chemical standpoint. To the best of the authors’ knowledge, this review is the first compilation of literature on indophenine-based semiconducting materials covering their scope, limitations, and applications. In the first section, we briefly introduce some of the organic electronic devices that are the basic building blocks for certain applications involving organic semiconductors (OSCs). We introduce the definition of key performance parameters of three organic devices: organic field effect transistors (OFET), organic photovoltaics (OPV), and organic thermoelectric generators (TE). In section two, we review recent progress towards the synthesis of quinoidal semiconducting materials. Our focus will be on indophenine family that has never been reviewed. We discuss the relationship between structural properties and energy levels in this family of molecules. The last section reports the effect of structural modifications on the performance of devices: OFET, OPV and TE. In this review, we provide a general insight into the association between the molecular structure and electronic properties in quinoidal materials, encompassing both small molecules and polymers. We also believe that this review offers benefits to the organic electronics and photovoltaic communities, by shedding light on current trends in the synthesis and progression of promising novel building blocks. This can provide guidance for synthesizing new generations of quinoidal or diradical materials with tunable optoelectronic properties and more outstanding charge carrier mobility.

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“…However, to our knowledge, the extension of the ThBF structure was highly limited, probably due to the very limited and harsh synthetic methods. 6,9,11 Traditionally, ThBF could be obtained from intermediate 9,9 0 -(thiophene-2,5-diyl)bis(9H-fluoren-9-ol) (1, Scheme 1) via heating at around 200 1C or irradiation with a yield of up to 86%. 6 Besides, SnCl 2 was also found to efficiently promote such transformation.…”

Section: Introductionmentioning

confidence: 99%

“…However, to our knowledge, the extension of the ThBF structure was highly limited, probably due to the very limited and harsh synthetic methods. 6,9,11…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,5-bis(9H-fluoren-9-ylidene)-2,5-dihydrothiophene derivatives and a systematic study of the substituent effect

Jiang

Cai

et al. 2022

New J. Chem.

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Design and synthesis of two conjugated semiconductors containing quinoidal cyclopentadithiophene core

Cited by 7 publications

References 40 publications

Excitation localization/delocalization induced intramolecular singlet fission in cyclopentadithiophene-based quinoidal derivatives

Excitation localization/delocalization induced intramolecular singlet fission in cyclopentadithiophene-based quinoidal derivatives

Recent Research Progress in Indophenine-Based-Functional Materials: Design, Synthesis, and Optoelectronic Applications

Synthesis of 2,5-bis(9H-fluoren-9-ylidene)-2,5-dihydrothiophene derivatives and a systematic study of the substituent effect

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