Supramolecular Ensemble of Perylene Bisimide Derivative and Cu₂O-Ag Nanoparticles: Nano/“Dip Strip” Catalytic System for One-Pot, Three-Component Click Reaction at Room Temperature

Abstract

A supramolecular ensemble of Cu 2 O-Ag nanoparticles (NPs) and aggregates of perylene bisimide (PBI) derivative has been developed in mixed aqueous media. The as prepared supramolecular ensemble exhibits high catalytic efficiency in the one-pot, three-component click reaction for the preparation of 1,2,3-triazoles under "green" conditions (room temperature, mixed aqueous media, and recyclable catalytic system). The catalytic system also works efficiently for the synthesis of isatin and coumarin derivatives having pharmaceutical importance. Interestingly, a "dip strip", prepared by dip coating a filter paper strip with the solution of the supramolecular ensemble, serves as an efficient heterocatalytic system for the one-pot, three-component reaction. The as prepared dip strip could be reused efficiently for the one-pot, three-component click reaction up to five cycles.

Rational Design and Synthesis of Ag−Cu2O Nanocomposites for SERS Detection, Catalysis, and Antibacterial Applications

“…Only small amounts of Ag(CH 3 COO) was used to create an eyeball‐shaped hybrid, where a small Ag particle is attached to a larger Cu 2 O sphere. Meanwhile, Singh and co‐workers made use of a perylene bisimide (PBI) derivative in their preparation of Janus Ag−Cu 2 O nanocomposites [41] . The PBI derivative first formed supramolecular aggregates in H 2 O/THF (1 : 1) solvent mixture, and these aggregates served as the reductant and the stabilizer that facilitated the formation of the Janus hybrid.…”

Pyrazine Based Type‐I Sensitizing Assemblies for Photoreduction of Cu(II) in ‘One‐Pot Three‐Component’ CuAAC Reaction Under Aerial Conditions

“…These studies indicate the potential of PDA assemblies to stabilize Cu(I) ions for the cycloaddition reaction. By increasing either the amount of CuI or the PDA assemblies, no significant change in the yield of the target product is observed (Table S4, entries [18][19].…”

“…Recently, from our lab, we reported a supramolecular catalytic ensemble PBI@Cu 2 OÀ Ag for 'one-pot three-component' CuAAC at room temperature in mixed aqueous media. [19] The Cu 2 OÀ Ag nanocomposite was developed by using supramolecular ensemble of PBI derivative in combination with Benedict solution and silver nanoparticles. The PBI assemblies also served as stabilizers for the as prepared nanocomposite.…”

Development of a Novel Three‐step Sonogashira Cross Coupling/Deacetonation/Cycloaddition Protocol for the Synthesis of 4‐aryl‐1,2,3‐triazoles Using 2‐methyl‐3‐butyn‐2‐ol as a Versatile Acetylene Surrogate

“…1-(4-nitrobenzyl)-4-(4-nitrophenyl)-1H-1,2,3-triazole (5 j). [24] Yield: 55.4 mg (57%). Rf = 0.3 (Hexane/AcOEt -1 : 1).…”