Synthesis of benzo[1,2‐<i>b</i>′:4,5‐<i>b</i>′]dithiophene and its 4,8‐Dimethoxy and 4,8‐dimethyl derivatives

Beimling, Peter; Koßmehl, Gerhard

doi:10.1002/cber.19861191025

Cited by 78 publications

(48 citation statements)

References 10 publications

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“…It ( Scheme 6 a) successfully realized double thiophene-ring annulation in good yields. On the other hand, 4,8-disubstituted derivatives ( 17c [ 55a ] and 17d [ 62 ] ) were also effectively synthesized from BDT-4,8-dione, [ 66 ] which could be prepared from commercially available 3-thiophene carboxylic acid (Scheme 6 b). Selective syntheses of the angular-shaped isomers ( 22 and 23 ) were achieved from 2-or 3-thiophene aldehyde, respectively (Scheme 6 c,d).…”

Section: Discussionmentioning

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: Discussionmentioning

confidence: 99%

Thienoacene‐Based Organic Semiconductors

et al. 2011

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“…11 The decomposition of 16 is lower than those of 17 and 18, this result can be explained due to less thermal stability of benzo [1,2- 17 and 18 showed that all of the three oligomers are crystalline and it is expected that their thin films are well ordered under heat treatment.…”

Section: Resultsmentioning

confidence: 79%

“…The preparation of 2,6-dibromobenzo[1,2-b:4,5-b']dithiophene 11 17 and 2,9-dibromoanthracene 14 18 were synthesized according to literature procedures, respectively (Scheme 2). The 2,6-dibromonaphthalene 15 was purchased from Alfa Aesar Co.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Physical Properties of Decylbithiophene End-Capped Oligomers Based on Naphthalene, Anthracene and Benzo[1,2-b:4,5-b']dithiophene

Tai¹,

Kim²,

Han³

et al. 2009

Bulletin of the Korean Chemical Society

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The new candidates for OTFTs, which were composed of naphthalene, anthracene, benzo[1,2-b:4,5-b']dithiophene and 2-decylbithiophene end-capper were synthesized under Suzuki coupling reaction conditions. All of the oligomers were characterized by FT-IR, mass analysis, UV-vis, PL spectrum, cyclic voltametry (CV), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), 1 H-NMR and 13 C-NMR. Investigation of physical properties showed that all of the oligomers have higher oxidation potential and good thermal stability. Especially, DBT-DtB-DBT is soluble in common solvents and suitable for low cost processing technologies.

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“…The first syntheses of anti-BDT 1 reported by Kossemehl et al 17 and Katz et al 18 are based on thiophene derivatives as precursors. Other synthetic routes start from the functionalized benzene core 3a with TMS-acetylene via palladium catalyzed Cassar-Heck-Sonogashira coupling, 19 followed by intramolecular cyclization (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

2,6-Bis(tributyltin)benzo[1,2-b:5,4-b’]dithiophene: a new synthon for organic semiconductors

Boone¹,

Dienes²,

Baumgartner³

2008

Arkivoc

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A new tin-functionalized benzo [1,2-b:5,4-b']dithiophene building block was synthesized that can provide access to a series of further extended π−conjugated materials for Organic Field-Effect Transistors (OFETs) via Stille coupling protocol, as exemplified in two cases. The synconfigured benzodithiophene scaffold complements the well-established (anti) benzo [1,2-b:4,5-b']dithiophene unit that has already been successfully employed in OFET devices. DFT-quantum theoretical calculations on a series of organic semiconductors support the selective modification of the band gap by either changing the HOMO, the LUMO, or both. The suitability of the tinfunctionalized synthon to efficiently access a variety of organic semiconductor materials with different properties was also confirmed by the study of their photophysical features.

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Synthesis of benzo[1,2‐b′:4,5‐b′]dithiophene and its 4,8‐Dimethoxy and 4,8‐dimethyl derivatives

Cited by 78 publications

References 10 publications

Thienoacene‐Based Organic Semiconductors

Thienoacene‐Based Organic Semiconductors

Synthesis and Physical Properties of Decylbithiophene End-Capped Oligomers Based on Naphthalene, Anthracene and Benzo[1,2-b:4,5-b']dithiophene

2,6-Bis(tributyltin)benzo[1,2-b:5,4-b’]dithiophene: a new synthon for organic semiconductors

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