Synthesis of 1,5-naphthylethynyl nanostructure networks with extended π-conjugation. Effective heterocoupling catalyzed by palladium under a compatible CO2 atmosphere

Rodriguez, Jose Gonzalo Gonzalez; Tejedor, J. Luis

doi:10.1016/s0040-4039(03)00344-7

Cited by 14 publications

(6 citation statements)

References 11 publications

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“…Thus, the terminal acetylene p- [5-(dimethylamino)naphthyl-1-ethynyl]phenylacetylene (3) was obtained by the heterocoupling reaction between 1-(dimethylamino)-5-ethynylnaphthalene (1) and 4-(p-iodophenyl)-2-methyl-3-butyn-2-ol in the presence of dichlorobis(triphenylphosphane)palladium(ii) and cuprous iodide in freshly distilled triethylamine, under a rigorous carbon dioxide atmosphere, [16] to give 4-(4-{[5-(dimethylamino)-1-naphthyl]-ethynyl}-1-phenyl)-2-methyl-3-butyn-2-ol (2) as a yellow solid in excellent yield (96%; Scheme 1). The homocoupling product 1,4-bis[5-(dimethylamino)-1-naphthyl]buta-1,3-diyne was obtained as a minor product (2%).…”

Section: Resultsmentioning

confidence: 99%

End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)_x Branches on a 1,3,5‐Substituted Benzene Core

Rodriguez

Tejedor

2005

Eur J Org Chem

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Alternating (1‐naphthylethynyl‐p‐phenylethynyl)x 1,3,5‐trisubstituted benzene dendrons were efficiently synthesised by the heterocoupling reaction between (1‐naphthylethynyl‐p‐phenyl)xacetylene (x = 1) and 1,3,5‐triiodobenzene in the presence of a palladium‐copper catalyst system. A longer terminal acetylene chain (x = 2) was obtained from the heterocoupling between 1,3,5‐tri(1‐ethynyl‐5‐naphthylethynyl)benzene and the appropriate iodoaryl derivative. The alternating chains, and their dendron structures, show fluorescence emission, with similar wavelengths and quantum yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Resultsmentioning

confidence: 99%

End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)_x Branches on a 1,3,5‐Substituted Benzene Core

Rodriguez

Tejedor

2005

Eur J Org Chem

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“…Bis(triphenyl phosphine)palladium(II) dichloride, [22] 4-(5-iodonaphthalen-1-yl)-2-methylbut-3-yn-2-ol [23] and 4-(2,5-dialkoxyl-4-iodophenyl)-2-methylbut-3-yn-2-ol [24] were prepared by the method reported in the literatures. All the other reagents and chemicals were purchased from Aldrich or Acros Chemical Company without purification prior to use.…”

Section: Methodsmentioning

confidence: 99%

A series of linear π conjugated arylene oligomers based on 1,5-naphthalene subunit: synthesis, characterization, and properties

Men

et al. 2014

Designed Monomers and Polymers

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Gao (2014) A series of linear π conjugated arylene oligomers based on 1,5-naphthalene subunit: synthesis, characterization, and properties, Designed Monomers and Polymers, 17:7, 684-692, DOI: 10.1080/15685551.2014 A series of novel alkoxy-substituted arylene-ethynylene oligomers based on 1,5-naphthalene subunit have been successfully synthesized by palladium-catalyzed cross-coupling reaction. The solubility, thermal, optical, and electrochemical properties have been investigated in detail. The title compounds are soluble in common organic solvents and emit a blue color both in solution and in the solid state, indicating that these oligomers might serve as potential materials in optoelectronic devices.

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“…The naphthalenethynylene-type polymers or oligomers were the outstanding representatives, for different ways can be used to link the naphthalene units [28,29]; e.g., Rodriguez and co-workers have successfully synthesized large numbers of naphthalenethynylene-type oligomers, such as 1,5-naphthalene nanostructures [30,31], 1,5-bis(p-phenylethynyl)naphthalene nanostructures [31] and a series of end-capped, conjugated (dimethylamino) naphthyl nanostructures with alternating (1-naphthylethynyl-p-phenylethynyl) x branches on a 1,3,5-or 1,4substituted benzene core [32][33][34][35], and indicated that these oligomers exhibited excellent quantum yields for the fluorescent emission. However, poor solubility of these oligomers remained the most serious problem.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Properties of 1,4-Bis(Naphthalen-1-Ylethynyl)Benzene and Its Derivatives: Monomers of Oligomers or Polymers Based on Linear 1,4-Phenylethynyl or 1,5-Naphthylethynyl Subunits

Men

et al. 2011

Designed Monomers and Polymers

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A series of novel monomers of oligomers or polymers based on linear 1,4-phenylethynyl or 1,5naphthylethynyl subunits, 1,4-bis(naphthalen-1-ylethynyl)benzene (8a) and its derivatives (8b-8i), has been synthesized and characterized. The UV absorption and fluorescence emission properties of these compounds were analyzed and discussed through the energy gap ( E) between HOMO and LUMO orbitals, the orbital diagrams and the charge densities of related carbon atoms. It is evident from these results that the introduction of the electron-donating substituent (-OR) to the central phenylene ring of 8a and the introduction of electron-withdrawing substituent (-NO 2 ) to the end of the conjugated system can efficiently improve its solubility, give rise to red-shift of maximum absorption and emission wavelength. But the introduction of electron-withdrawing substituent (-NO 2 ) will lead dramatically decrease in fluorescence efficiency. The novel synthesized compounds 8b-8e have potential prospects as the monomers of oligomers or polymers based on linear 1,4-phenylethynyl or 1,5-naphthylethynyl subunits for their excellent solubility and optical properties.

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Synthesis of 1,5-naphthylethynyl nanostructure networks with extended π-conjugation. Effective heterocoupling catalyzed by palladium under a compatible CO2 atmosphere

Cited by 14 publications

References 11 publications

End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)_x Branches on a 1,3,5‐Substituted Benzene Core

End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)_x Branches on a 1,3,5‐Substituted Benzene Core

A series of linear π conjugated arylene oligomers based on 1,5-naphthalene subunit: synthesis, characterization, and properties

Synthesis, Characterization and Properties of 1,4-Bis(Naphthalen-1-Ylethynyl)Benzene and Its Derivatives: Monomers of Oligomers or Polymers Based on Linear 1,4-Phenylethynyl or 1,5-Naphthylethynyl Subunits

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Synthesis of 1,5-naphthylethynyl nanostructure networks with extended π-conjugation. Effective heterocoupling catalyzed by palladium under a compatible CO2 atmosphere

Cited by 14 publications

References 11 publications

End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)x Branches on a 1,3,5‐Substituted Benzene Core

End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)x Branches on a 1,3,5‐Substituted Benzene Core

A series of linear π conjugated arylene oligomers based on 1,5-naphthalene subunit: synthesis, characterization, and properties

Synthesis, Characterization and Properties of 1,4-Bis(Naphthalen-1-Ylethynyl)Benzene and Its Derivatives: Monomers of Oligomers or Polymers Based on Linear 1,4-Phenylethynyl or 1,5-Naphthylethynyl Subunits

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End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)_x Branches on a 1,3,5‐Substituted Benzene Core

End‐Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1‐Naphthylethynyl‐p‐phenylethynyl)_x Branches on a 1,3,5‐Substituted Benzene Core