Synthesis and Structural Characterization of Mono Acid-type partial Cone Conformation Azocalix[4]arene

Year 2022, Volume: 6 Issue: 1, 24 - 28, 07.05.2022

Serkan Elçin

Abstract

The synthesis of chromogenic mono acid-type azocalix[4]arene derivatives is described in this study. From p-tertbutylcalix[4]arene, which was made with p-tert-butylphenol as a starting material, a new family of azocalix[4]arene monocarboxylic acid derivatives (5a-d) were synthesized. Four azocalix[4]arenes (3a-d) were produced by attaching 4-methoxy-, 4-ethyl-, 4-chloro-, and 4-bromoaniline to 25,26,27,28-tetrahydroxycalix[4]arene through a diazo-coupling reaction. To obtain partial cone conformation acid derivatives, their mono ester units were synthesized with ethyl bromoacetate and hydrolyzed in a basic media (5a-d). Products were obtained in suitable (79-92 %) yields, with 25-(carboxymethoxy)-26,27,28- trihydroxy-5,11,17,23-tetra(4-methoxyphenyl)azocalix[4]arene (5a) being the product with the highest yield (92 %). FT-IR and 1H-NMR spectroscopy approaches, as well as elemental analysis techniques, were used to elucidated the synthesized
products.

Keywords

Structural Properties, Azocalix[4]arene, Calix[n]arene, Diazo-coupling Reaction, Partial Cone Conformation

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