One-pot Synthesis of Benzo[b]thiophenes and Benzo[b]selenophenes from o-Halo-Substituted Ethynylbenzenes: Convenient Approach to Mono-, Bis-, and Tris-Chalcogenophene-Annulated Benzenes

Kashiki, Tomoya; Shoji, Shuichi; Kohara, Masahiro; Miyazaki, Eigo; Takimiya, Kazuo; Ikeda, Masaaki; Kuwabara, Hirokazu

doi:10.1021/ol900809w

Cited by 180 publications

(82 citation statements)

References 34 publications

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“…[ 56 , 62 ] Then, much easier methods for the synthesis of the same core using thiophene annulation chemistries were developed. Starting from readily available 1,4-dibromo-2,5-di(ethynyl)benzenes, an initial Li-Br exchange reaction followed by a reaction with elemental sulfur, [ 63 , 64 ] or a simple thermal reaction with sodium sulfi de nonahydrate as the reagent in N -methylpyrrolidone (NMP) [ 65 ] Scheme 6 . Representative syntheses of BDT isomers.…”

Section: Synthesis and Variation Of Acdtsmentioning

confidence: 99%

Thienoacene‐Based Organic Semiconductors

et al. 2011

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Thienoacenes consist of fused thiophene rings in a ladder-type molecular structure and have been intensively studied as potential organic semiconductors for organic field-effect transistors (OFETs) in the last decade. They are reviewed here. Despite their simple and similar molecular structures, the hitherto reported properties of thienoacene-based OFETs are rather diverse. This Review focuses on four classes of thienoacenes, which are classified in terms of their chemical structures, and elucidates the molecular electronic structure of each class. The packing structures of thienoacenes and the thus-estimated solid-state electronic structures are correlated to their carrier transport properties in OFET devices. With this perspective of the molecular structures of thienoacenes and their carrier transport properties in OFET devices, the structure-property relationships in thienoacene-based organic semiconductors are discussed. The discussion provides insight into new molecular design strategies for the development of superior organic semiconductors.

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Section: Synthesis and Variation Of Acdtsmentioning

confidence: 99%

Thienoacene‐Based Organic Semiconductors

et al. 2011

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“…As presented in Figure , the 17 compounds are ranked based on the number of Se atoms while the 13 – 17 are listed at last. For the crystal structures, it can be categorized into five types based on their packing symmetry elements . The first also the simplest one is the material with molecules in transfer layers stacking as central symmetry, which includes 4 , 9 , 11 – 17 .…”

Section: Resultsmentioning

confidence: 99%

Anisotropic charge carrier transport of optoelectronic functional selenium‐containing organic semiconductor materials

et al. 2020

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Organic semiconductors (OSCs) materials are currently under intense investigation because of their potential applications such as organic field‐effect transistors, organic photovoltaic devices, and organic light‐emitting diodes. Inspired by the selenization strategy can promote anisotropic charge carrier migration, and selenium‐containing compounds have been proved to be promising materials as OSCs both for hole and electron transfer. Herein, we now explore the anisotropic transport properties of the series of selenium‐containing compounds. For the compound containing SeSe bond, the SeSe bond will break when attaching an electron, thus those compounds cannot act as n‐type OSCs. About the different isomer compounds with conjugated structure, the charge transfer will be affected by the stacking of the conjugated structures. The analysis of chemical structure and charge transfer property indicates that Se‐containing materials are promising high‐performance OSCs and might be used as p‐type, n‐type, or ambipolar OSCs. Furthermore, the symmetry of the selenium‐containing OSCs will affect the type of OSCs. In addition, there is no direct relationship between the R groups with their performance, whether it or not as p‐type OSCs or n‐types. This work demonstrates the relationship between the optoelectronic function and structure of selenium‐containing OSCs materials and hence paves the way to design and improve optoelectronic function of OSCs materials.

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“…Compounds 1a-1c were synthesized via selective Sonogashira coupling of 1,4-dibromo-2,5-diiodobenzene with corresponding alkyl alkyne in high yields. 33 The synthesis of intermediates 4 and 8 that contain 3,5-dien-1-yne moieties began with commercially available 3-bromo-2-naphthol. First, hydroxide group was converted to triflate group.…”

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confidence: 99%