34904-19-3

Upstream product

• 34993-56-1 1-ethynylpyrene 
• 199920-14-4 4-(4-iodophenyl)-1,3-butanediol 

Relevant academic research and scientific papers

A closely-coupled pyrene dimer having unusually intense fluorescence

A synthetic route is described for the preparation of 1,4-di(1-pyrenyl) butadiyne. The target compound, after purification by extensive column chromatography, has been characterized by NMR and exact-mass spectrometry. This material is highly-fluorescent in solution and, relative to pyrene, strongly absorbing in the near-UV region. Phosphorescence is observed at 77 K and formation of the metastable triplet state has been confirmed by laser flash photolysis. In marked contrast to pyrene, fluorescence from the target compound is not susceptible to self-quenching nor to the presence of dissolved oxygen. The average conformation of the molecule has been established by molecular modeling. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Preparation of poly(silylene-p-phenylene)s containing a pendant fluorophor and their applications to PL imaging

Poly(silylene-p-phenylene)s bearing an anthrylethynyl, pyrenylethynyl, or terthienyl group as the pendant were obtained in moderate yield, by substitution reactions of poly[ethoxy(methyl)silylene-p-phenylene] with the corresponding organolithium reagents in THF. The polymers exhibited photoluminescent (PL) properties in solutions as well as in the films. They were photoactive and irradiation of the films in air with a low-pressure mercury lamp led to a decrease of PL efficiencies, being applicable to PL imaging of the films. The present polymers can be used also as hole-transporting materials in double-layer electroluminescent (EL) devices and the devices with the structure of ITO/polymer film/Alq3/Mg-Ag emitted a green EL arising from Alq3 emission.

Copper-Mediated Deacylative Coupling of Ynones via C-C Bond Activation under Mild Conditions

The intermolecular deacylative coupling of unstrained ynones via C-C bond activation was accomplished by a CuCl-bpy system under mild reaction conditions. This protocol features facile cleavage of the C-C bond at room temperature, broad substrate scope, and efficient construction of important symmetric and unsymmetrical 1,3-diyne adducts through homo or cross coupling of ynones, respectively. The preliminary mechanistic investigations indicated that an acyl copper(III) complex is likely involved in this process.

Subnanometer gold clusters on amino-functionalized silica: An efficient catalyst for the synthesis of 1,3-diynes by oxidative alkyne coupling

Subnanometer (d = 0.8 ± 0.2 nm) gold particles homogeneously dispersed on amino-functionalized silica catalyze Glaser-type alkyne coupling, providing corresponding 1,3-diynes under mild conditions. Readily available λ3-iodane PhI(OAc)2 is used as an oxidant and 1,10-phenanthroline is used as an additive. Ten symmetrical 1,3-diynes and three products of heterocoupling containing various functionalities are isolated in high yields. The catalyst can be recycled at least five times, giving consistently high isolated yields and maintaining the size and distribution of gold clusters. This unique combination of stable subnanometer gold clusters and hypervalent iodine thus paves a hitherto unexplored avenue in organic synthesis employing heterogeneous gold catalysis. (Chemical Equation Presented).

Photophysical properties of symmetrically substituted diarylacetylenes and diarylbuta-1,3-diynes

A series of symmetrically substituted diarylacetylenes and diaryl-1,3-butadiynes were prepared and studied with an emphasis on their spectral and photophysical properties. The photophysical characteristics of these compounds were studied in relation to their structures and the influence of solvent or temperature. The observed spectral and photophysical properties are explained using potential energy maps of the ground and excited states obtained from density functional theory calculations. The structure-property relationships of all of the compounds are discussed and compared with the appropriate diphenylacetylene and diphenyl-1,3-butadiyne derivatives.

1-(Phenylethynyl)pyrene and 9,10-bis(phenylethynyl)anthracene, useful fluorescent dyes for DNA labeling: Excimer formation and energy transfer

A series of novel modifying reagents, including phosphoramidites and solid supports, have been synthesized, and used for the introduction of 1-(phenylethynyl)pyrene (PEPy) and 9,10-bis(phenylethynyl)anthracene (BPEA) fluorescent dyes into predetermined positions of synthetic oligonucleotides. These two fluorophores have been shown to constitute an energy donor-acceptor pair, and can be used as such in fluorescent oligonucleotide probes, designed for the detection and structural studies of nucleic acids. The sensitivity of the probe to duplex formation is demonstrated. The formation of the PEPy and BPEA excimers is reported for the first time on nucleic acids. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.