Calix[4]resorcinarene macrocycles

Abstract

Supramolecular chemistry is an interdisciplinary scientific field, including chemical, physical and biological properties of more complex chemical species than the molecules themselves. Calixarenes/calixresorcinarenes are macrocyclic compounds, consisting of 'n' phenolic/resorcinolic units linked together by methylene bridges; these macrocycles are often used for molecular recognition. Thus, different modifications can be made to both the lower and upper rim, allowing the construction of well-defined multivalent buildings. In this work, three calix[4]resorcinarene macrocycles were synthesized, namely C-dec-9-en-1-ylcalix[4]resorcinarene (CAL 11U), C-trans-2, cis-6-octa-1,5-dien-1-ylcalix[4]resorcinarene (CAL 9U) and C-nonylcalix[4]resorcinarene (CAL 10) by a simple condensation reaction. The compounds CAL 11U and CAL 10 have been already synthesized by researchers, while the CAL 9U has been synthesized for the first time. Their structures were confirmed using ATR-FTIR, 1 H NMR and 13 C NMR. Thermal analysis combined with mass spectrometric evolved analysis of the vapors was used to study the thermal behavior of the different synthesized molecules, and they were the subject of characterization by X-ray powder diffraction in order to analyze their degree of crystallinity.

Calix[4]Resorcinarene Macrocycles Interactions with Cd2+, Hg2+, Pb2+, and Cu2+ Cations: A QCM‐I and Langmuir Ultra‐thin Monolayers Study

“…Both ionophores (I) and (II) were prepared from C-dec-9-en-1-ylcalix [4]resorcinarene (A) and are structurally and chemically characterized in earlier work [25,40].…”

“…One of the vital menaces affecting together the human health and the ecosystem, is the so called “Heavy metals (HM) ions toxicity”, the (HM) exposure or release can be of both natural and artificial origins (e. g. industrial productions, medical treatments…etc.) . However, some of the metals ions (Cu, Zn, etc.)…”

“…Those methods are extremely sensitive and selective, but are expensive, time‐consuming, and requiring expert skills. Non‐conventional detection methods, known as sensors technology, are offering great alternatives to the traditional methods, in terms of ease of use, operating time, cost effectiveness and being excellently sensitive and selective .…”

“…Macrocycles sensing networks have a subtype manifests in calixarenes and calixresorcinarenes, which are considered as third‐generation macrocyclic compounds after crown‐ethers and cyclodextrines. Due to their amphiphilic and host‐guest properties towards cations, anions, and neutral molecules, they were immensely employed in sensing and recognition applications .…”

Application of the Langmuir Technique to Study the Response of C-dec-9-en-1-ylcalix[4]resorcinarene and C-undecylcalix[4]resorcinarene Ultra-thin Films' Interactions with Cd2+, Hg2+, Pb2+, and Cu2+ Cations Present in the Subphase

“…The cyclocondensation synthesis, the chemical, and the structural characterization of the ionophores (I) and (II) were described in our previous work (Eddaif et al 2019d); additionally, the synthetic approaches are presented in Fig. 2.…”