SYNTHESIS OF POLY-5,7-DIALLYL-25,26,27,28-TETRAHYDROXYCALIX[4]ARENE

Desi Suci Handayani; Jumina Jumina; Maulidan Firdaus; Triana Kusumaningsih

doi:10.22146/ijc.21492

SYNTHESIS OF POLY-5,7-DIALLYL-25,26,27,28-TETRAHYDROXYCALIX[4]ARENE

https://doi.org/10.22146/ijc.21492

Desi Suci Handayani^(1*), Jumina Jumina⁽²⁾, Maulidan Firdaus⁽³⁾, Triana Kusumaningsih⁽⁴⁾

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Jl. Ir. Sutami 36A Kentingan Surakarta 57126; Postgraduate Student of Chemistry Department, Faculty of Mathematic and Natural Sciences, Universitas Gadjah Mada
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Jl. Ir. Sutami 36A Kentingan Surakarta 57126
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Jl. Ir. Sutami 36A Kentingan Surakarta 57126
(*) Corresponding Author

Abstract

The synthesis of poly-5,7-diallyl-25,26,27,28-tetrahydroxycalix[4]arene were performed in experimental series as follows: (1) Cyclotetramerization of p-t-butylphenol with NaOH and paraformaldehyde to p-butylcalix[4]arene, (2) Debutylation of p-butylcalix[4]arene using AlCl₃and phenol to tetrahydroxycalix[4]arene, (3) Allylation reaction using allylbromide to diallyloxy-dihydroxycalix[4]arene, (4) Claisen rearrangement reaction, (5) Cationic polymerization to diallylcalix[4]arenes. All of the synthesized products were analyzed by means of IR spectrometer and ¹H-NMR spectrometer. The result of 25,27-diallyloxy-26,28-dihydroxycalix[4]arene synthesis was white crystals having m.p. 205-207 °C in 80.95% yield. The synthesis of 5,7-diallyl-25,26,27,28-tetrahydroxy-calix[4]arene gave light yellow crystals having m.p. 214-216 °C in 78.67% yield. The polymerization gave poly(5,7-diallyl-25,26,27,28-tetra-hydroxycalix[4]arene) having m.p. 338-340 °C, in 60% yield. Its estimated has a relative molecular weight of 18,738 g/mol with the number of unit repetition about 37 monomer units.

Keywords

Diallylation; polymerization; Poly-5,7-diallyl-25,26,27,28-tetrahydroxycalix[4]arene

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DOI: https://doi.org/10.22146/ijc.21492