Synthesis of the First Thieno[3,4-c]thiophene Stabilized Only by Electronic Effects

Beye, N.; Cava, Michael P.

doi:10.1021/jo00087a045

Cited by 40 publications

(10 citation statements)

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“…[139][140][141] However, until now only a few examples of this class of compounds have been synthesized while many of them, and in particular the unsubstituted derivative (21, R ) H) are unstable and have only been detected by trapping experiments as cycloaddition products. 141 The corresponding oligomers and polymer have been theoretically evaluated but there was little …”

Section: Fused Thiophenesmentioning

confidence: 99%

“…Thieno[3,4- c ]thiophenes with a 10-electron system and sulfur in the formal oxidation state +4 ( 21 ) have been the subject of synthetic and theoretical interest for more than 20 years. − However, until now only a few examples of this class of compounds have been synthesized while many of them, and in particular the unsubstituted derivative ( 21 , R = H) are unstable and have only been detected by trapping experiments as cycloaddition products …”

Section: Fused Thiophenesmentioning

confidence: 99%

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Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems

1997

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Section: Fused Thiophenesmentioning

confidence: 99%

Section: Fused Thiophenesmentioning

confidence: 99%

Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems

1997

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“…The synthesized compounds containing a hypervalent sulfur atom have attracted much attention for their interesting structures and reactivities. They are generally unstable and only a few isolable derivatives have been synthesized 83a. Furthermore, benzobis(thiadiazole) derivatives were found to show strong electron‐accepting properties 83b.…”

Section: Application In Light Technologymentioning

confidence: 99%

2,1,3‐Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules

et al. 2012

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2,1,3‐Benzothiadiazole (BTD) is one of the most important nuclei used in the chemistry of photoluminescent compounds and applicable for light technology. The understanding of its properties and reactions is fundamental for the design and application of these derivatives in molecular organic electronic devices and for other technologies. As a result of their potential as constituents of organic light‐emitting diodes, solar cells, liquid crystals, dyes, photovoltaic cells, and many others, attention has been focused on BTD π‐extended derivatives with potential use in this exciting area. Herein, we describe their syntheses, properties, reactions, and selected examples of applications in light technology using by BTD (small molecules) as the core.

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“…Thieno[3,4- c ]thiophenes have attracted much attention from both theoretical and spectroscopic viewpoints as 10 π-electron heterocycles with nonclassical structures. However, the synthesis of thieno[3,4- c ]thiophenes is not easy, and only a limited number of thieno[3,4- c ]thiophenes, including tetraphenyl, tetrakis(alkylthio), tetra(2-thienyl), tetrabromo, 1,3-dibromo-4,6-dicyano 5 and 1,3-dibromo-4,6-bis(methoxycarbonyl)-substituted derivatives, are known. Of these compounds, 1,3,4,6-tetrakis(alkylthio)thieno[3,4- c ]thiophenes can be synthesized conveniently in one step from bis(alkylthio)cyclopropenethiones and triphenylphosphine or tributylphosphine, although the yields were not high.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactivity of New 1,4-Bis(alkylthio)-3,6-diarylthieno[3,4-c]thiophene Derivatives

et al. 1998

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1,4-Bis(tert-butylthio)-3,6-diphenyl- and 3,6-di(2-thienyl)thieno[3,4-c]thiophenes (2a,b)were synthesized from 2-(tert-butylthio)-3-phenyl- and 3-(2-thienyl)cyclopropenethiones (1a,b) and triphenylphosphine in dry benzene at 50 degrees C, although similar treatment of 2,4,6-triisopropylphenyl, N,N-diethylamino, pyrrolidino, and diphenyl-substituted cyclopropenethiones (1c-h) did not result in the production of the corresponding thieno[3,4-c]thiophene derivatives. The possible reaction pathway for the formation of 2a,b is described. The protonation of 2a with trifluoroacetic acid (TFA) gave 4-(tert-butylthio)-3,6-diphenylthieno[3,4-c]thiophene-1(3H)-thione (13a), the treatment of which with sodium hydride and then isopropyl iodide led to 4-(tert-butylthio)-3,6-diphenyl-1-(isopropylthio)thieno[3,4-c]thiophene (16) by the regeneration of the thieno[3,4-c]thiophene ring system, this making possible the synthesis of other alkylthio-substituted thieno[3,4-c]thiophene derivatives. The reactions of 2a,b with N-phenylmaleimide (NPM) gave predominantly the endo-cycloadducts (17a,b) at the 1- and 3-positions, and that of 2a with dimethyl acetylenedicarboxylate (DMAD) led to the benzo[c]thiophene derivative (19) by desulfurization.

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Synthesis of the First Thieno[3,4-c]thiophene Stabilized Only by Electronic Effects

Cited by 40 publications

References 1 publication

Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems

Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems

2,1,3‐Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules

Synthesis and Reactivity of New 1,4-Bis(alkylthio)-3,6-diarylthieno[3,4-c]thiophene Derivatives

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