Synthesis and characterization of partially substituted at lower rim phosphorus containing calix(4)arenes

Emil Stefanov Tashev (1) , Tania Dimitrova Tosheva (2) , Stoycho Dimitrov Shenkov (2) , Anne-Sophie Chauvin (3) , Victoria Lachkova (4) , Rosica Petrova Petrova (5) , Rosario Scopelliti (3) , Sabi Genchev Varbanov (2)

1 Institute of Polymers
2 Institute of Polymers
3 Laboratory of Lanthanide Supramolecular Chemistry
4 Deptartment of Ecology
5 Central Laboratory of Mineralogy and Crystallography

Abstract: We report the synthesis and characterization of several new phosphorus-containing partially lower rim substituted derivatives of 5,11,17,23-tetra(t-butyl) calix(4)arene (I) and 5,11,17,23-tetra(t-octyl)calix(4)arene (II), namely 5,11,17,23-tetra(t-butyl)-25,27-dihydroxy-26,28-bis(diphenyl phosphinoyl-oxy) calix(4)arene (IV); 5,11,17,23-tetra(t-butyl)-25-hydroxy-26,27,28-tris(tetramethyldiamido-phosphinoyl-oxy) calix(4)arene (Vb); 5,11,17,23-tetra(t-butyl)-25,27-dihydroxy-26,28-bis(dimethyl- phosphinoyl-methoxy) calix(4)arene (VI); 5,11,17,23-tetra (t-octyl)-25,27-dihydroxy-26,28-bis(dimethyl-phosphinoyl-methoxy) calix(4)arene (VII). The structure of the synthesized calix(4)arene derivatives are identified and confirmed by elemental analysis, IR-, 1H-, 13C-, 31P{1H} – NMR-spectroscopy and mass spectrometry as and X-ray crystallographic analysis of 5,11,17,23-tetra(t-butyl)-25,27-dihydroxy-26,28-bis(dimethyl- phosphinoyl-methoxy) calix(4)arene VI. According to the NMR spectra, all calix(4)arenes are in cone conformation.

Mots clés: Physical Sciences

Emil Stefanov Tashev, Tania Dimitrova Tosheva, Stoycho Dimitrov Shenkov, Anne-Sophie Chauvin, Victoria Lachkova, et al.. Synthesis and characterization of partially substituted at lower rim phosphorus containing calix(4)arenes. Supramolecular Chemistry, 2007, 19 (07), pp.447-457. ⟨10.1080/10610270601105703⟩. ⟨hal-00513499⟩