alpha-Naphthaldehyde and Certain of its Derivatives

Coles, Harold W.; Dodds, Mary L.

doi:10.1021/ja01271a023

Cited by 19 publications

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“…Reaction of benzo[ b ]furan in acetic acid as a solvent with CH 2 O and HCl produced 3‐(chloromethyl)benzofuran. Benzo[ b ]furan‐3‐acetonitrile ( 2 ) was prepared by the reaction of 3‐(chloromethyl)benzofuran with potassium cyanide in EtOH/H 2 O 41 . Finally, the new heterocyclic system 3‐alkyl‐3 H ‐benzofuro[2,3‐ b ]pyrazolo[4,3‐ f ]quinoline‐12‐carbonitrile ( 3a‐e ) was produced in KOH/MeOH by a one‐pot reaction of precursors 1a‐e with 2 in good yields (see Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, electrochemical, photophysical, and photovoltaic properties of new fluorescent compounds: 3 H ‐benzofuro[2,3‐ b ]pyrazolo[4,3‐ f ]quinoline

et al. 2021

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Summary The concern with fluorescent heterocyclic compounds has been growing because they can be utilized in dye‐sensitized solar cells (DSSCs) as organic photosensitizers. As a result of the experiment we conducted, the following outcomes emerged: new fluorescent heterocyclic systems 3H‐benzofuro[2,3‐b]pyrazolo[4,3‐f]quinolines ensued from reaction of 1‐alkyl‐5‐nitro‐1H‐indazole with 2‐(benzofuran‐3‐yl)acetonitrile in KOH/MeOH. New heterocyclic compounds were characterized through a use of elemental analysis and spectroscopic data. The results of the optical properties of the fluorescent compounds demonstrated that their fluorescence quantum yields are comparable to the quantum yields of such well‐known fluorescent dyes as fluorescein. Furthermore, the cyclic voltammetry revealed the electrochemical attributes of the fluorescent heterocyclic systems and that reversible oxidation waves are observable in their case. In order for their photovoltaic performance parameters to be determined, the I‐V curves and the IPCE spectra of the new compounds were launched into an investigation. What followed exposed that the photovoltaic performances of the foregoing compounds were 5.01% to 5.17%.

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Section: Resultsmentioning

confidence: 99%

“…Compounds 1a‐e 40 and 2 41 were synthesized in accordance with the proceedings related in the literature. The other reagents were purchased from Merck and Sigma‐Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, electrochemical, photophysical, and photovoltaic properties of new fluorescent compounds: 3 H ‐benzofuro[2,3‐ b ]pyrazolo[4,3‐ f ]quinoline

et al. 2021

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“…Initial reaction of naphthalene with paraformaldehyde and HCl in HOAc led to the formation of 1-chloromethylnaphthalene. 26 Subsequent treatment of 1-chloromethylnaphthalene with KCN in alcohol and water produced 1-naphthylacetonitrile (2) in good yield. 27 Synthesis, characterisation, optical properties and theoretical calculations of a new fluorescent heterocyclic system: 3H-benzo[a]pyrazolo [3,4-j]acridine…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 1a-d 25 and 2 26,27 were synthesised according to the literature procedures. Other reagents and solvents were purchased from Merck.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, characterisation, optical properties and theoretical calculations of a new fluorescent heterocyclic system: 3H-benzo[a]pyrazolo[3,4-j]acridine

Alipoor

Pordel

Morsali

2017

Journal of Chemical Research

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Four new fluorescent dyes derived from the 3 H-benzo[ a]pyrazolo[3,4- j]acridine system were synthesised and fully characterised by 1H NMR, 13C NMR, mass and analytical data. These new fluorophores were prepared from the reaction of 1-alkyl-5-nitro-1 H-indazoles with 1-naphthylacetonitrile via nucleophilic substitution of hydrogen, in high yields. The optical properties of the dyes were also investigated and the results revealed that, in some cases, they have higher quantum yields compared with well-known fluorescent dyes such as fluorescein. Solvent effects on the fluorescence characteristics of the four compounds indicated that the emission wavelength is red-shifted with increasing solvent polarity. Furthermore, density functional theory calculations using the B3LYP hybrid functional and the 6-311++G(d,p) basis set provided the optimised geometries and relevant frontier orbitals of the compounds. Calculated electronic absorption spectra were also obtained using the time-dependent density functional theory method.

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“…The vapor-phase oxidation of benzyl alcohol by air or oxygen under reduced pressures has been conducted with yields up to 90 per cent by using such catalysts as silver metal, cupric oxide, or vanadium pentoxide at temperatures of 100- A simple reaction for converting substituted benzyl halides to the corresponding benzaldehyde derivatives, and one that is quite general, is Sommelet's reaction , which consists in refluxing the benzyl halide with hexamethylenetetramine in dilute alcohol, acidifying, and isolating the aldehyde by steam distillation (36,196,254,271). The yields average 60-70 per cent.…”

Section: Indirect Methodsmentioning

confidence: 99%