The synthesis of selenium and tellurium core-modified carbaporphyrinogens was carried out by the reaction of functional selenophene/tellurophene diols with azulene or a benzitripyrrane in the presence of acid. The products were obtained in moderate yields and were characterized by using H andC NMR, UV-vis, FT-IR, CV, and HRMS spectroscopic techniques. Further, oxidation of the obtained core-modified carbaporphyrinogens in the presence of DDQ in CHCl afforded the corresponding carbaporphyrins in good yields. Benziporphyrins showed no indication of a ring current or macrocyclic aromaticity as confirmed by using proton NMR spectroscopy, but the addition of TFA gave rise to the formation of weakly diatropic dications.
Superbenzene porphyrin conjugates find wide range of applications from nonlinear optical materials to semiconductors. Herein, we report the synthesis and characterization of 5,15-bis(3,5-di-tert-butylphenyl)-10,20-bis-(pentaphenylphenyl)phenylporphyrin and its Zinc-metallated complex. Oxidative planarization of 5,15-bis(3,5-di-tert-butylphenyl)-10,20-bis(pentaphenylphenyl)phenylporphyrin and its metallated complex was carried out by using NOBF 4 as an oxidizing agent. The formation of superbenzene porphyrin conjugates validates its Scholl type reactions. The laboratory-synthesized porphyrin conjugates were characterized experimentally using spectroscopic techniques such as 1 H NMR, 13 C NMR, electron spin resonance, and ultraviolet−visible spectroscopy for structural conformation. In addition, density functional theory calculations were carried out to validate the experimental results. The theoretical and experimental results show that the 4-(pentaphenylphenyl)phenyl ligand increases the stability, optical properties, and rate of planarization of synthesized porphyrins. The conjugates exhibited intense and distant electronic communication between two hexabenzocoronene sites, taking advantage of porphyrin as a π-spacer. The π-radical cation has also been found to be an intermediate in oxidative C−C bond formation. NICS calculations support such a conclusion.
Background:
Quinolines represent an important class of bioactive molecules which are present in
various synthetic drugs, biologically active natural compounds and pharmaceuticals. Quinolines find their potential
applications in various chemical and biomedical fields. Thereby, the demand for more efficient and simple
methodologies for the synthesis of quinolines is growing rapidly.
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Objective: The green one-pot Friedlander Synthesis of Functionalized Quinolines has been demonstrated by
using graphene oxide as a carbocatalyst.
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Method: The graphene oxide catalyzed condensation reaction of 2–aminoaryl carbonyl compounds with different
cyclic/ acyclic/ aromatic carbonyl compounds in methanol at 70°C affords different quinoline derivatives.
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Results: The reaction has been examined in different protic and aprotic solvents and the best yield of quinoline
is observed in methanol at 70°C.
Conclusion:
The present method of quinoline synthesis offers various advantages over other reported methods
such as short reaction time, high yield of product, recycling of catalyst and simple separation procedure. The
graphene oxide carbocatalyst can be easily recovered from the reaction mixture by centrifugation and then can
be reused several times without any significant loss in its activity.
Engineering of porphyrin based imine linked supramolecular cages and MOFs for electrocatalysis and photocatalysis is summarized. Their broad applications for artificial photosynthesis and energy conversion were discussed.
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