ChemicalBook CAS DataBase List tris(4-(pyridin-4-ylethynyl)phenyl)amine

tris(4-(pyridin-4-ylethynyl)phenyl)amine synthesis

7synthesis methods

Product Name:tris(4-(pyridin-4-ylethynyl)phenyl)amine
CAS Number:359647-66-8
Molecular formula:C39H24N4
Molecular Weight:548.63

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tris(4-(pyridin-4-ylethynyl)phenyl)amine

359647-66-8
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Yield:359647-66-8 85%

Reaction Conditions:

Stage #1: p-iodopyridine;4,4',4''-triethynyltriphenylamine in 1,4-dioxane;lithium hydroxide monohydrate; for 0.166667 h;Inert atmosphere;Sonogashira Cross-Coupling;
Stage #2: with [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II);copper (I) iodide;tetrakis-(triphenylphosphine)-palladium in 1,4-dioxane;lithium hydroxide monohydrate at 90; for 12 h;Inert atmosphere;

Steps:

4.3. General procedure for Sonogashira cross-coupling(chromophores 4-6)

General procedure: The appropriate mono-, di- or tri-acetylene TPA derivative(200 mg) and 4-iodopyridine were dissolved in a mixture ofdioxane/piperidine (25 mL, 4/1). Ar was bubbled through themixture for 10 min and [Pd(PPh3)4] and CuI were added. The reactionmixture was stirred at 90° C for 12 h. The cooled reactionmixture was diluted with H2O (50 mL) and extracted with CH2Cl2(2 50 mL). The combined organic extracts were thenwashed withsaturated NH4Cl solution, brine, and dried. Finally, the solventswere evaporated under vacuum and the crude productwas purifiedby column chromatography (SiO2, appropriate eluent).

References:

Tydlitát, Ji?í;Achelle, Sylvain;Rodríguez-López, Julián;Pytela, Old?ich;Mikysek, Tomá?;Cabon, Nolwenn;Robin-le Guen, Fran?oise;Miklík, David;R??i?ková, Zdeňka;Bure?, Filip [Dyes and Pigments,2017,vol. 146,p. 467 - 478]

2510-22-7 Synthesis