Pyrene Derivate Functionalized with Acetylene for Organic Field Effect Transistors
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Abstract:
A new X-shaped compound (SiPy) functionalized with acetylene bonds in the 1-, 3-, 6-, and 8-positions of the pyrene core has been synthesized by Sonogashira coupling reactions. Its photophysical, thermal, and organic field effect transistor (OFET) properties as well as the film morphologies have been investigated. SiPy exhibits high stability which is evidenced by thermal gravimetric analysis. The atomic force microscopy images reveal that the morphology of thin films depends on the substrate temperature. The film OFET devices based on SiPy were constructed and exhibited p-type performances.Keywords:
Sonogashira coupling
Organic field-effect transistor
Acetylene
Thermal Stability
Gravimetric analysis
Efficient method for the total synthesis of egonol in five steps via Sonogashira coupling reaction is reported.
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Sonogashira cross-coupling reaction is one of the most important reactions of forming new C—C bond and alkynylation,and metal catalysts play an important role.In this paper the application of various transition metals as catalyst in the Sonogashira cross-coupling reaction is reviewed.Meanwhile,the application of palladium catalysts in green Sonogashira cross-coupling reaction and other transition metal catalysts in Sonogashira cross-coupling reaction are introduced.Pd/C catalyst may be a new candidate in the industrial application of Sonogashira cross-coupling reaction,and water,suitable catalyst system and alkaline system play an essential role in improving environmental compatibility.
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3-Iodoindoles, 5-bromo-3-iodoindoles and 5-bromo-3-iodoindazoles have been studied with respect to their reactivity and selectivity in palladium catalyzed Sonogashira and Suzuki cross-coupling reactions. As a result, sequential Sonogashira-Sonogashira, Sonogashira-Suzuki, and Suzuki-Sonogashira reactions with 5-bromo-3-iodoindoles or indazoles were used to obtain a large range of new functionalized indoles and indazoles, which are potential 5-HT receptor ligands.
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Indazole
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Abstract Maleimides are involved for the first time in Sonogashira cross‐coupling reactions. Sonogashira conditions have been developed to allow subsequent coupling of various terminal alkynes at room temperature in moderate to excellent yields. These results open the way to innovative synthesis strategies for various difunctionalized maleimide derivatives.
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Maleimide
Coupling reaction
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Host–guest complexation between γ-cyclodextrin (γ-CD, cyclo-octa-amylose) and pyrene has been studied in detail by fluorescene and induced circular dichroism (i.c.d.) spectra. γ-CD forms complexes with pyrene with 1 : 1, 1 : 2, 2 : 1, and 2 : 2 stoicheiometries at ambient temperature. The inclusion of pyrene by γ-CD proceeds stepwise; γ-CD including only one pyrene molecule can accommodate a second pyrene molecule to produce a 1 : 2 and/or 2 : 2 complex. Both in a monomolecularly dispersed pyrene solution and in a suspended pyrene solution, several hours are required for γ-CD to include two pyrene molecules. The configuration of two pyrenes included is an S-helix. At temperatures above ca. 85 °C, a 1 : 1 complex alone is formed mainly, where a pyrene molecule is accommodated with its long axis parallel to the axis of γ-CD. The data are compared with those of the systems containing β-CD (cyclohepta-amylose) in place of γ-CD.
Helix (gastropod)
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Sonogashira coupling
Coupling reaction
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Hitherto unknown pentaalkynylpyridines have been prepared in high yields by Sonogashira cross-coupling reactions of pentachloropyridine. Their photophysical properties were studied and compared to those of penta- and hexaalkynylbenzenes which were efficiently prepared by the first Sonogashira reactions of pentachlorobenzene and hexachlorobenzene. The pentaalkynylpyridines show promising fluorescence properties because of their high quantum yields.
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Hexachlorobenzene
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Abstract A simple and efficient Sonogashira cross‐coupling reaction of cyclic 3‐bromo‐1,2‐diketones with substituted acetylenes is developed.
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Coupling reaction
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Fraction (chemistry)
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Abstract The utility of Sonogashira cross-coupling reactions in organic synthesis is indisputable. However, the palladium catalytic Sonogashira reaction in mild condition is still in its infancy. Here, we reported the synthesis of a fluorescent nucleoside analog by using a copper-free Sonogashira cross-coupling reaction in a satisfactory yield. This reaction occurred at 37 °C in the open air and aqueous medium, and avoided the toxicity of Cu(I). The mild Sonogashira reaction provided the possibility of fluorescent labeling of nucleoside mimics in living cells. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]
Sonogashira coupling
Aqueous medium
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Nucleoside analogue
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