C–H oxidation and chelation of a dipyrromethane mediated rapid colorimetric naked-eye Cu(ii) chemosensor

Abstract

Copper(ii) ion mediated C-H oxidation of dipyrromethanes (DPMs) to the corresponding dipyrrins followed by complexation invoked the selective sensing of copper(ii) ions in aqueous solutions. On the addition of copper, the colour of the DPM solution instantaneously changes from yellow to pink with the detection limit of 0.104 μM measured by absorption spectroscopy, whereas visible colour changes could be observed by the naked eye for concentrations as low as 3 μM.

5-Hydroxymethylfurfural-Derived Boron-Dipyrromethene Immobilized on Resin Support as a Sustainable Catalyst for C–H Arylation of Heterocycles

“…Previously, we have developed a facile method to access HMF from fructose at room temperature, utilizing silica as a solid support, mitigating humin formation, and facilitating selective extraction of HMF . Also, we have strategically utilized 2,4-dimethylpyrrole (DMP) in developing a colorimetric naked-eye chemosensor for copper­(II) ions. , Here, we have utilized these two sustainable raw materials (HMF and DMP) in developing a sustainable photocatalyst with an objective to mitigate our dependency on fossil-based chemicals. A retrosynthetic scheme originating from sustainable raw materials including 5-hydroxymethylfurfural (HMF), succinic anhydride, and 2,4-dimethylpyrrole was designed to access the photocatalyst (Scheme ).…”

Current Advances in the Synthesis of Valuable Dipyrromethane Scaffolds: Classic and New Methods

“…Copper nanoparticles (CuNPs) [78] and celite-supported glycine (glycine@celite) [79] have been explored as catalysts in the synthesis of dipyrromethanes because they are easily removed from the reaction medium and can be reutilized (Scheme 21). The reaction of aromatic aldehydes with pyrrole (10 equiv) under solvent-free conditions using CuNPs as catalyst gave dipyrromethanes 7c , e , 58d and 103 in high yields (65%–77%).…”

“…The reaction of aromatic aldehydes with 2,4-dimethylpyrrole (3 equiv) in the presence of 10 mol% of the catalyst in dichloromethane for 30 min gave the corresponding dipyrromethanes 104 in very good yields (Scheme 21). The authors described the reuse of the catalyst for 5 cycles without any deterioration and with similar catalytic activity [79].…”

“…Dipyrromethane 104e underwent oxidation and chelation by copper producing a red bis(dipyrrinato)copper(II) complex 105 (Scheme 22). This characteristic makes it an efficient naked eye colorimetric chemosensor for copper ions, even in the presence of several other metal ions [79,80].…”

A novel boronic acid-based fluorescent sensor for selectively recognizing Fe3+ ion in real time

“…However, the selectivity of voltammetry is poor, and atomic absorption spectroscopy needs higher requirements on instruments and more expensive analysis cost. Due to the simple operation, high sensitivity and selectivity, uorescence spectroscopy has been widely applied to detect various ions (Cu 2+ , [9][10][11][12][13][14][15] Cr 3+ , 16 Hg 2+ , [17][18][19][20][21] Al 3+ , 22,23 etc. ), carbohydrates [24][25][26][27] and so on.…”