Synthesis of Novel Tris-Crown Ether Structures

Abstract

Six unique tris-crown ether structures were successfully synthesized from trimethylolpropane triacrylate (TMPTA) with amino-and aza-crown ethers through Michael addition. The crown ethers contained a primary amine group such as 2-aminomethyl crown ethers and 4-aminobenzo crown ethers, others contained a secondary amine group, like 1-aza crown ethers.

{[[K.18-Crown-6]Br3}n: A tribromide catalyst for the catalytic protection of amines and alcohols

“…Crown ethers have attracted significant attention in various fields of science. Crown ether moieties are popular host compounds in host-guest chemistry, and these ligands have a remarkable ability to selectively form strong complexes with organic and inorganic cations [1][2][3] and anions [4,5]. Among the crown ethers, the 18-crown-6 forms a very stable complex with K + , and it has the maximum stability constant among alkali complexes with metal cations [6,7].…”

Synthesis and Crystal Structure Determination of [H2‐cryptand 222](Br3)2: A Unique Tribromide Catalyst for the Catalytic Chemoselective N‐Boc Protection of Amines

“…Crown ether moieties are popular host compounds in host-guest chemistry and these ligands have shown a remarkable ability to form strong complexes with organic and inorganic cations [1][2][3] or anions, 4,5 selectively. Among the crown ethers, cryptand 222, a macrobicyclic compound, has been used in a variety of applications including the formation of a conductometric mercury [II] sensor based on poly aniline, 6 the encapsulation of alkali metals, especially K + , [7][8][9] use as an acceptor ligand for the formation of complexes containing 7,7,8,8-tetracyanoquinodimethane (TCNQ), 10 extraction of uranium(VI), 11 exchanging the cations of micas 12 and extraction of copper(II) with erythrosine B.…”

Synthesis, Characterization, and Binding Properties of Novel Penta-Crown Ethers

“…Multi-site crown ethers have attracted considerable attention due to their fascinating structures and coordination properties with guest cations [1][2][3][4][5][6][7][8][9][10][11][12] and their application in synthetic, host-guest, and supramolecular chemistry. [13][14][15][16][17][18][19][20] A multi-site crown ether and some of its derivatives have found applications in quite widespread areas; their main application was their use as ionophores and host compounds.…”

“…When the cation size exceeds that of the crown ether unit cavity such as in the 'butterfly crown ethers', [23][24][25][26] it may form a host/guest 2:1 sandwich-type complex. [23][24][25][26][27][28][29][30][31] In our previous work, [17][18][19][20] we found an efficient synthetic approach to tris-, tetra-and penta-crown ethers by Michael addition using multi-acrylates as the linker. The triacrylate of trimethylolpropane triacrylate (TMPTA) has proven to be a useful linker to prepare multi-site crown ethers.…”

“…TMPTA was synthesized as described elsewhere. 18 TMPTA usually plays an important role in the field of polymer chemistry, it contains three branch chains, each branch chain has the perfect length, and all are very flexible. Here, the 2-aminomethyl-15crown-5 was designed to serve as the parent crown ether unit, and TMPTA acted as the linker.…”