Synthesis of Photo-Switchable Derivatives of p-tert-Butyl Thiacalix[4]arenes Containing Ethoxycarbonyl and 4-Amidoazobenzene Fragments in the Lower Rim Substituents

Abstract

New p-tert-butyl thiacalix[4]arene derivatives containing simultaneously the 4-amidoazobenzene and ethoxycarbonyl fragments at the lower rim in cone and

Pillar[5]arenes with Morpholide and Pyrrolidide Substituents: Synthesis and Complex Formation with Alkali Metal Ions

“…The residue from the reaction mixture was filtered off and washed with distilled water for several times. 4,8,14,18,23,26,28,31,32,35-Deca(carboxymethoxy)pillar [5] arene (4). Product yield: 0.40 g (83 %).…”

“…[16] In this work, we used first way which consists of step-by-step functionalization of the initial perhydroxylated pillar [5]arene 2. This approach was successfully applied to the synthesis of the thiacalix [4]arene derivatives and made it possible to obtain functionalized macrocycles with high yields. [17][18][19][20] Perhydroxylated pillar [5]arene 2 has ten reactive OH groups and modification of the OH groups can provide various functionalized pillar [5]arene derivatives.…”

“…Previously, the pillar [5]arene containing ethoxycarbonyl fragments 3 was synthesized by interaction of perhydroxylated pillar [5] arene 2 with ethyl bromoacetate in the presence of potassium carbonate in acetonitrile (Scheme 1). The base and solvent were specified in accordance with their efficiency in alkylation of p-tert-butyl thiacalix [4]arene at the lower rim. [4,17] Besides, KI as catalyst was used in alkylation to increase the product yield.…”

“…The literature describes a variety of cage-like organic molecules with accessible internal cavities, e.g., crown ethers, [1] cyclodextrins, [2] cucurbiturils, [3] and calixarenes, [4][5][6] which can serve as hosts. In recent years, a new class of synthetic macrocycles -pillar[n]arenesattracts the interest of researchers.…”

Synthesis of p-tert-butylthiacalix[4]arenes functionalized with tris(2-aminoethyl)amine fragments at the lower rim and their interaction with model lipid membranes

“…[28][29][30] Cup-like structure of calix [4]arenes presents a suitable molecular platform for constructing on their basis threedimensional structures with wide range of cavity sizes, differing in number and type of binding centers, spatial arrangement of binding groups and also offers a possibility of forming asymmetric cavities and varying balance between rigidity and flexibility of receptor. [31,32] The current main objective is functionalizing the thiacalix [4]arene molecular platform with TREN fragments and their interaction with model lipid membranes.…”