A water-soluble, tetrasulfonated calix[4]arene with a methylene-bridge substituent was prepared from a 2-(ω-haloalkyl)-substituted tetrahydroxy-p-tert-butylcalix[4]arene (1). Calixarene 1 was converted by ipso-sulfonation to tetra(p-sulfonato)calix[4]arene 2 by treatment with concentrated sulfuric acid at ambient temperature for 5 h. Compound 2 was converted to its sodium salt (3) by ion exchange. Transformation of the ω-halide 3 to an ω-azide (4) was achieved by treatment of 3 with 2 equiv NaN3 in H2O for 48 h at 100 °C. The purity of the compounds was judged by 1H NMR spectroscopy in D2O and DMSO-d6; infrared spectroscopy showed an absorption for the azide group of 4 (2108 cm–1). Efforts to covalently attach calixarene 4 to multiwall carbon nanotubes (MWCNT) by thermal decomposition of the azide and reaction between an intermediate nitrene and MWCNT, and the subsequent characterization of these products, will be described.

Synthesis of water-soluble tetrasulfonated calix[4]arenes with a reactive methylene-bridge substituent

253rd National Meeting (2017)

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