A Fused Selenocycle as a Stable Organic Semiconductor

Takimiya, Kazuo; Kunugi, Yoshihito; Konda, Yasushi; Ebata, Hideaki; Toyoshima, Y.; Otsubo, Toru

doi:10.1055/s-2006-934511

Cited by 15 publications

(10 citation statements)

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“…In general, for all the chalcogenophene series, extension of the acene core gave higher-lying E HOMO and smaller E g as in the case for oligoacene series (e.g., anthracene, tetracene, and pentacene), 20 which can be well represented by the schematic energy diagram (Figure 3). On the other hand, the furan homologues in all the benzo-, naphtho-, and anthradichalcogenophene series tend to have lower-lying E HOMO and larger E g than those of the thiophene and selenophene counterparts.…”

Section: ■ Inroductionmentioning

confidence: 68%

Isomerically Pure Anthra[2,3-b:6,7-b′]-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

et al. 2012

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A new straightforward synthesis of isomerically pure anthra[2,3-b:6,7-b'] -difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS) from readily available 2,6-dimethoxyanthracene is described. The present successful synthesis makes it possible to overview the linear-shaped anti-acenedichalcogenophene compounds, that is, benzo[1,2-b:4,5-b']-, naphtho[2,3-b:6,7-b']-, and anthra[2,3-b:6,7-b']- difuran, -dithiophene, and -diselenophene. By comparing their electrochemical and photochemical properties, the electronic structures of acenedichalcogenophenes can be expressed as the outcome of balance between the central acene core and the outermost chalcogenophene rings. Among isomerically pure parent anti-anthradichalcogenophenes, anti-ADT and anti-ADS can afford crystalline thin films by vapor deposition, which acted as active layer in organic field-effect transistors with mobility as high as 0.3 cm(2) V(-1) s(-1) for ADT and 0.7 cm(2) V(-1) s(-1) for ADS. The mobility of isomerically pure anti-ADT is higher by several times than those reported for isomercally mixed ADT, implying that the isomeric purity could be beneficial for realizing the better FET mobility. We also tested the diphenyl derivatives of anti-ADF, -ADT, and -ADS as the active material for OFET devices, which showed high mobility of up to 1.3 cm(2) V(-1) s(-1).

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Section: ■ Inroductionmentioning

confidence: 68%

Isomerically Pure Anthra[2,3-b:6,7-b′]-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

et al. 2012

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“…This could be related to the existence of anti/syn isomers inevitably formed in the synthesis, which might cause structural defects or carrier traps in the semiconducting channel. In this regard, it should be noted that the anti isomers always give mobilities that are several orders of magnitude higher than those of the syn isomers in both BDT [ 78 ] and NDT derivatives ( Figure 13 ).…”

Section: Synthesis and Variation Of Acdtsmentioning

confidence: 95%

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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“…On the other hand, Larock and co-workers employed o -alkynyl-thioanisole or -selenoanisole in the electrophilic cyclization reaction to give benzo[ b ]-thiophenes and -selenophenes, respectively, where o -methylthio or methylseleno groups are an excellent chalcogen source . The superiority of these new methods was proved by the high yields of the desired products, the tolerance for various substituents, and successful applications to 2-fold cyclization reactions to give benzo[1,2- b :4,5- b ′]dithiophenes and benzo[1,2- b :5,4- b ′]diselenophenes …”

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confidence: 99%

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

et al. 2009

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A convenient one-pot procedure for the synthesis of benzo[b]thiophenes and selenophenes from readily available o-halo-ethynylbenzene precursors is described. Regardless of the substituent on the acetylene terminus or the number of cyclization moieties on the precursors, various benzo[b]thiophenes and selenophenes, including not only the parent, alkyl-, and phenyl-substituted derivatives but also benzo[1,2-b:4,5-b']dithiophenes and diselenophenes and benzo[1,2-b:3,4-b':5,6-b'']trithiophenes and triselenophenes can be prepared in good to high yields.

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A Fused Selenocycle as a Stable Organic Semiconductor

Cited by 15 publications

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Isomerically Pure Anthra[2,3-b:6,7-b′]-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

Isomerically Pure Anthra[2,3-b:6,7-b′]-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

Thienoacene‐Based Organic Semiconductors

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

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