Beilstein J. Org. Chem.2009,5, No. 59, doi:10.3762/bjoc.5.59
their potential receptor properties for cations, anions and neutral molecules, calixarenes have enjoyed widespread use in various areas of science and technology. One of their successful applications as sensors is in analytical chemistry. They are useful for separations, enrichment, and analyses of
ionic and neutral molecular species [1][2][3][4]. In particular, the ion-selective electrode (ISE) is an important target in analytical applications [5][6][7][8][9][10]. To improve the ion selectivity of calixarenes, a great deal of effort has been devoted to the design and synthesis of novel
functionalized calixarenes in recent years [1][2][3][4]. In fact, a large number of calixarene derivatives containing pendant ether, amide, ketonic, ester and crown ether groups have been employed in studies of ISEs sensitive to sodium ions [11][12][13][14][15][16][17][18][19][20], potassium ions [21][22][23][24
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Graphical Abstract
Scheme 1:
Synthesis and structures of calix[4]arenes 6–8; 3, 6: n = 2; 4, 7: n = 3; 5, 8: n = 5.
Beilstein J. Org. Chem.2008,4, No. 36, doi:10.3762/bjoc.4.36
; organofluorine; (perfluoroalkyl)alkyl aryl ethers; Introduction
Calixarenes [1] are one of the most useful types of macrocyclic scaffolds. Since first reported by Zinke and Ziegler [2], calix[4]arenes have been used for a variety of molecular recognition, nanotechnology, and supramolecular applications. These
extraction of organic substrates into a fluorous liquid phase via hydrogen bonding [21].
Combining the selective nature of fluorous chemistry with the extensive molecular recognition capabilities of calixarenes should generate a scaffold for selective molecular receptors, yet few reports exist that detail
the synthesis and applications of fluorous calixarenes [22][23][24][25][26]. There are no reports of studies of solubilities of such calixarenes in fluorous solvents. The work reported herein is focused on synthesizing fluorous calixarenes that are easily functionalized for selective molecular