Synthesis and Structure Elucidation of Chromogenic Calix[4]arene Indophenols Capped by Carboxamide Bridges

Abstract

Calix[4]arenes capped by di‐ and triamide bridges on the lower rim were used to synthesize 2,3,4,5 chromogenic molecules supplied with indophenol indicator unit(s). The endo/exo quinoid tautomerism of the chromophore and the mechanism of the coloration process were studied by NMR spectroscopy.

Calixarene modified montmorillonite: a novel design for biosensing applications

“…[26][27][28] Treatment of the diester derivative 3 with tris(2-aminoethyl\mine in the presence of MeOH/toluene led to produce compound 4 according to the literature procedure. 29 Then, a mixture of compound 4 with 65% HNO 3 in DCM was reacted at room temperature for 1 h yielded the p-nitro substituted derivative 5. Upon reduction of nitro groups with Raney-Ni, the target compound 6, which was functionalized at the both rims of Calix with the primary amine groups, was synthesized in 95% yield (see Scheme 1).…”

“…p-tert-Butylcalix [4]arene (1), calix [4]arene (2), 1,3-O-dimethyl ester calix [4]arene derivative 3 and the compound 4 N-(2-aminoethyl)calix [4]azacrown were synthesized according to literature procedures. [26][27][28][29] The compounds 5 5,17-dinitro-25,27-bis[N-(2aminoethyl)]calix [4]azacrown and 6 5,17-diamino-25,27-bis[N-(2-aminoethyl)]calix [4]azacrown are herein reported for the rst time.…”

A new perylene bisimide-armed calix[4]-aza-crown as “turn on” fluorescent sensor for Hg2+ ion and its application to living cells

“…The synthesis of p-tert-butylcalix [4]arene (2) and its derivatives (3 and 4) was performed according to the reported literature procedure [35][36][37].…”

“…For the desired goal, a novel perylene derivative bearing calix [4]arene moieties was synthesized by using p-tertButylcalix[4]-aza-crown 4 and 3,4,9,10-perylenetetracarboxylic dianhydride 1 as the precursors. The synthetic route is shown in Scheme 1. p-tert-Butylcalix [4]arene 2 and its derivatives (3 and 4) were synthesized according to the reported literature procedure [35][36][37]. p-tert-Butylcalix[4]-aza-crown 4 was refluxed with 3,4,9,10-perylenetetracarboxylic dianhydride 1 in DMF to give PB-CX [4] in 80% yield.…”

Non-trivial solution chemistry between amido-pyridylcalix[4]arenes and some metal salts

“…The calix [4]arene diester compound 2 19,25 was heated to reflux for 120 h with 2-(aminomethyl)pyridine in a methanol-toluene solvent mixture (Scheme 1), similar to that previously described. 18,26 The reaction yielded the amide 3 as a white solid in good yield. Compound 3 has recently been reported by Rao using a different preparative route, 24 and the 1 H NMR data are comparable in both cases.…”