Synthesis, Conformations and Extraction Properties of New Chromogenic Calix[4]arene Amide Derivatives

Abstract

The synthesis of a new series of chromogenic calix[4]arene derivatives is described. p-Tetrakis(phenylazo)calix[4]arenes substituted with tertiary amide groups at the lower rim were obtained. The O-substitution of 25,26,27,28-tetrahydroxy-11,23-bis(phenylazo)calix[4]arene (2) and 25,26,27,28-tetrahydroxy-5,17,11,23-tetrakis(phenylazo)calix[4]arene (3) to provide 26,28-bis{[(diethylamino)carbonyl]methoxy}-25,27-dihydroxy-11,23-bis(phenylazo)calix[4]arene (4), 26-{[(diethylamino)carbonyl]methoxy}-25,27,28-trihydroxy-5,11,17,23-tetrakis(phenylazo)calix[4]arene (5), 25,26,27,28-tetrakis{[(dialkylamino)carbonyl]methoxy}-5,11,17,23-tetrakis(phenylazo)calix[4]arene [alkyl = ethyl (6a), methyl (7)] and 26,28-bis{[(diethylamino)carbonyl]methoxy}-25,27-dihydroxy-5,11,17,23-tetrakis(phenylazo)calix[4]arene (8a) have been carried out by treatment of the precursors 2 and 3 with

Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications

“…Given the free phenolic units in the ionophoric ligand, as expected, the ionophore also displayed pH sensitivity in its absorption behaviour, which could allow for the use of the ionophore as a new pH-probe in the region of pH 6.5. Dumazet-Bonnamour and co-workers have also looked at chromogenic diamide-functionalised calix [4]arenes for the determination of a series of metal ions [230]. They reported the syntheses of a number of amide-substituted azocalixarenes: 297, bearing one tertiary amide group at the lower rim of the phenylazocalixarene, 296 and 299 with two, and 298 with four (Fig.…”

Impedance spectroscopic investigations of ITO modified by new Azo-calix[4]arene immobilised into electroconducting polymer (MEHPPV)

“…The sensing molecules used in this work, a 5,17-bis(4-nitrophenylazo)-26,28-dihydroxy-25,27-di(ethoxycarbonylmethoxy)-calix [4]arene (Azo-C [4]), have been synthesised and purified by the LACE (Laboratoire d'Application de la Chimie à l'Environnement) at ''Claude Bernard University, Lyon'' according to the previously reported synthesis route [25]. The new Azo-calix [4]arene derivative has been characterised by the presence of chromophores at the upper rim and an ester group at the lower rim.…”

“…In the present paper, we report sensor impedance studies of composite membranes formed by new Azocalix [4]arene esters [25] incorporated into an electroconducting polymer (MEHPPV) on ITO electrode. The phenomena occurring at the electrode/solution interface during the complexation process have been investigated by electrochemical impedance spectroscopy [26].…”

Ion sensing film optodes based on chromogenic calix[4]arene: application to the detection of Hg2+, Ni2+ and Eu3+ ions

“…The tetrakis-(phenylazo) calix [4]arene amide derivative, used in this report and presented in Fig. 1, has been synthesized according to previously described methods [32,33]. So, the choice of this material containing a conjugated chromogenic (-N=N-) is based on their optical response by changing their spectra upon the binding of metal cations.…”