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Aseel .k. Assi
Dr. Mohammad Abul Haj
2013 Factual of Science and Technology Introduction Calixarene is the cyclic oligmers or meta cycle phases that derive from the condensation reaction of phenols and formaldehyde under basic condition.
The word a calixarene is derived from calix or chalice because this type of molecule resembles avase and from the word arene that refers to the aromatic building block. Introduction ( cont .. ) Figure.1 Two Possible Rotational Modes of the
Phenol Units Introduction
Properties of Calixarene
Synthesis of Calixarene
Characterizations of Calixarene
Applications of Calixarene
References. Contents Figure.2 General Structures of Calixarenes Figure.3 Calixarene of 3D Figure.4 Examples of calixarenes Figure.5 Examples of calixarenes Properites of Calixarene : well defined oligomer.
large thermal stability as phenoplasts.
good chemical stability as phenoplasts.
very high melting points.
very low solubility in many solvents and good solubility in certain solvents.
possible functionalization, - good flexibility of many calixarene molecules.
large variety of calixarene molecules with various sizes of cavities.
good properties of complexation with metals and neutral molecules.
good properties of selective complexation.
not very expensive macrocycles compared with crown-ethers and cryptates, and high-value products as compared with phenoplasts. Synthesis of Calixarenes calixarenes are synthesized by two major methods: single-step, base-induced synthesis and multi-step syntheses, each having its own pro and con. The multi- step syntheses can be further classified as non-convergent stepwise synthesis and convergent stepwise synthesis. 1. Single-step, Base-induced Synthesis 2.Multi-step synthesis 2.1 Non-convergent Stepwise Syntheses 2.2 Convergent Stepwise Synthesis Characterizations of Calixarene by NMR Applications of calixarene Calixarenes are applied in enzyme mimetics, ion sensetiv electrodes or sensors, selective membrance, non linear
Calixarenes are often used as mobile phase additives for HPLC and chemically bonded stationary phase for both GC and HPLC
Calixarenes are promising materials for nanomedicine application (drug delivery systems diagrostics, scaffolds for drug design).
The applications of calixarenes in polymer synthesis.
Calixarene derivatives for treatment of wastewater. Principle of work
The principle of work is based on the capacity of calixarene to form host-guest compounds with dyes. Variation of fix residue as function of contact time Figure.10 1H NMR spectra of 5b. Structure of dye References H.M. Chawla, N.Pant, Bindu Srivastava, Elsevier, Tetrahedron 64(2008)10453-10458.
Weipu Zhu, Pengfei Gou, Zhiquam shen. Macromol. Symp. 2008, 261, 74-84.
Chenghua Ding, Kang Qu, Yongbo Li, Hongxia Liu, Baoxian Ye, Yangjie Wu, Shusheng Zhang. Elsevier, Journal of chromatography A, 1170 (2007) 73-81.
Victor Barba ,Rau'l Villamil , Rolando Luna , Carolina Godoy-Alca'ntar , Herbert , Hiram I. Beltran , Luis S. Zamudio-Rivera , Rosa Santillan , and Norberto Farfa'n. Inorg .Chem .2006, 45, 2553-2561.
GAURAV ARORA B.Tech. Submitted to the Graduate Faculty of Texas Tech University in Partial Fulfillment of the Requirements for the Degree of MASTER OF SCIENCE. December, 2006.
Robert Perrin, Roger Lamatine ET Monique Perrin .Pure & Apple. Chem, Vol.65, NO: 7, PP. 1549-1559. 1993 Figure.6 Figure.7 Figure.8 Figure.9 Figure.12 Figure Figure.13 Figure.11 According to this nomenclature, abracketed number is inserted between calix and arene , thus gives "Calix [n]aene", where n denotes the number of aryl groups. Therefore , a cyclic tetramer is called a "Calixarene" , acyclic hexamer is called a "Calixarene", and a cyclic octamer is a "Calix arene".
Calixarenes are built up by phenol and methylene units and possess several conformational isomers because of two possible rotational modes of the phenol units: the oxygen-through-the-annulus rotation and the para-substituent-through-the-annulus rotation Figure.14