A Facile and Efficient Synthesis of BODIPY-Based Fluorescent Probes for Selective Detection of Hydrazine.

A facile and ratiometric BODIPY-based fluorescent probe 4 was developed for the selective detection of hydrazine in solution phase. The BODIPY-based fluorophores 3 and 4 were easily prepared in high yields from the L-proline catalyzed reaction between α/β-formyl BODIPY 1 a/1 b and 3-cyanoacetylindole 2. Use of easily accessible substrates, benign solvent, catalytic amount of L-proline and high product yields are the advantageous features of the developed protocol.

BODIPY(aryl)iodonium salts in the efficient synthesis of diversely functionalized BODIPYs and selective detection of serum albumin.

BODIPY(aryl)iodonium salts were readily accessible from the high-yielding reaction of BODIPY with iodoarenes or hydroxyl(tosyloxy)iodoarenes in the presence of -CPBA. The prepared BODIPY(aryl)iodonium salts bearing substituents of varied electronic nature were utilized for the direct syntheses of thiocyanate, azide, amine and acrylate functionalized BODIPYs and β,β'-bis-BODIPYs. The regioselective syntheses of α-piperidinyl and β-piperidinyl substituted BODIPYs were achieved through the reaction of BODIPY(aryl)iodonium salts with piperidine in the absence and presence of copper(I).

Iodine(III)-promoted regioselective and efficient synthesis of β-triazolyl BODIPYs for the selective recognition of nickel ions and bovine serum albumin.

Various β-triazolyl tethered BODIPYs were efficiently prepared in a sequential one-pot protocol involving the initial reaction of BODIPY with iodobenzene diacetate (IBD) and sodium azide to generate BODIPY azides followed by a copper-catalyzed azide-alkyne cycloaddition reaction. Under the optimized reaction conditions, various β-triazolyl BODIPYs 5a-i were successfully prepared in good yields and adequately characterized by using UV, NMR, mass spectral data and XRD analyses. The UV-Visible spectra of the prepared β-triazolyl BODIPYs 5a-i showed intense absorption bands (514-545 nm) with a 13-44 nm red shift when compared with those of the parent BODIPY.