A perspective to resorcinarene crowns

Abstract

In this report, we have summarized different synthesis methods of the resorcinarene crowns, discussed their structural and complexation properties together with the possible application aspects.

Selective O-Alkylation of the Crown Conformer of Tetra(4-hydroxyphenyl)calix[4]resorcinarene to the Corresponding Tetraalkyl Ether

“…In 1a , two classes of hydroxyl groups are observed: eight hydroxyl groups from resorcinol residues in the upper rim of the resorcinarene system, which are stabilized by OH···O hydrogen bonds, forming a strong interaction and making them less reactive than the four hydroxyl groups from the pendant substituent (lower rim) under the reaction conditions. This tendency is confirmed by the results observed in the reaction of 2 with glycidyl methacrylate, which also does not generate the product of O -alkylation of hydroxyl groups and which supports our finding that the regioselectivity in the crown conformer of tetra(4-hydroxyphenyl)calix[4]resorcinarene is due to the strong hydrogen bonding in the upper rim between hydroxyl groups [ 2 , 27 , 35 , 36 ].…”

“…Investigation of resorcinarene derivatives provides a significant contribution to the development of new applications, including separation techniques and heterogeneous catalysts, among others. Resorcinarenes represent a class of macrocyclic phenolic compounds obtained from the condensation reaction of resorcinol with several aromatic and aliphatic aldehydes in acidic solutions [ 1 , 2 ], and they can be modified with various substituents on the upper and lower rim in order to provide specific functionality and selectivity. The many possible structural variations lead to potential applications, such as voltammetric sensors [ 3 ], dendrimer synthesis [ 4 , 5 ], dyeing of fibers [ 6 , 7 ], NMR solvating agents [ 8 , 9 ], chemical receptors for molecules and ions [ 10 , 11 , 12 ], and absorption of heavy metal ions [ 13 , 14 ].…”

Synthesis and Characterization of Two Sulfonated Resorcinarenes: A New Example of a Linear Array of Sodium Centers and Macrocycles

“…The resorcinarene moiety shows the four C -butyl chains in the lower rim, adopting an rccc configuration, which has also been observed for other resorcinarenes [21,22,23,24]. The bond lengths and angles are similar to those found in the reported examples, with C···C diagonal distances of C(14)···C(54) 5.198(6), C(34)···C(74) 5.162(4), C(20)···C(60) 7.152(5) and C(40)···C(80) 7.249(5) Å [20,21,22] (see Figure 3).…”

Reactions of resorcinarene with N,N-dimethylcarbamoyl and N,N-dimethylthiocarbamoyl chlorides. Factors affecting the process performance

“…Using these reactions, a broad range of polyfunctionalized derivatives of resorcinarenes have been synthesized; many of these compounds exhibit acceptor properties towards metal cations. [16][17][18][19][20][21] It is noteworthy that the receptor properties of the synthesized compounds and their selectivity are determined by pre-organization of the macrocyclic core of resorcinarene and the nature of the immobilized ionophoric groups.…”