Тɟɦɚɬɢɱɟɫɤɢɣ ɪɚɡɞɟɥ: ɉɪɟɩɚɪɚɬɢɜɧɚɹ ɯɢɦɢɹ. _________________________________ ɉɟɪɟɪɚɛɨтɚɧɧыɣ ɩɥɟɧɚɪɧыɣ ɞɨɤɥɚɞ ɉɨɞɪɚɡɞɟɥ: ɋɭɩɪɚɦɨɥɟɤɭɥɹɪɧɚɹ ɯɢɦɢɹ Ɋɟɝɢɫɬɪɚɰɢɨɧɧɵɣ ɤɨɞ ɩɭɛɥɢɤɚɰɢɢ: sm3 © Хɢɦɢɹ ɢ ɤɨɦɩɶɸɬɟɪɧɨɟ ɦɨɞɟɥɢɪɨɜɚɧɢɟ. Ȼɭɬɥɟɪɨɜɫɤɢɟ ɫɨɨɛщɟɧɢɹ. 2000. № 3. ________ ɍɥ. Ʉ. Ɇɚɪɤɫɚ, 68. 420015 Ʉɚɡɚɧɶ. Ɍɚɬɚɪɫɬɚɧ. Ɋɨɫɫɢɹ. _______ 55 ɉɨɫɬɭɩɢɥɚ ɜ ɪɟɞɚɤɰɢɸ 22 ɫɟɧɬɹɛɪɹ 2000 ɝ. ɍДɄ 547.52 ɋɈȼɊȿɆȿɇɇЫȿ ȾɈɋɌɂɀȿɇɂə ȼ ɈȻɅȺɋɌɂ ɏɂɆɂɂ ɄȺɅɂɄɋ[4] ɊȿɁɈɊɐɂɇȺɊȿɇȺ. © M. Pietraszkiewicz, 1 O. Pietraszkiewicz, 1 E. Uzig, 1 P. Prus, 1 Z. Brzózka, 2 K. Woźniak, 3 R. Bilewicz, 3 T. Borowiak, 4 and M. Mączyñski 4 1 Institute of Physical Chemistry Polish Academy of Sciences. 01224 Warsaw. Kasprzaka 44/52. Poland. E-mail: pietrasz@ichf.edu.pl 2 Department of Analytical Chemistry. Warsaw University of Technology. 00-664 Warsaw. Noakowskiego 3. Poland. 3 Department of Chemistry. University of Warsaw. 02093 Warsaw. Pasteura 1. Poland. 4 Department of Chemistry. A. Mickiewicz University. Grunwaldzka 6. 60-780 Poznan. Poland. _______________________________________________ *Вɟɞɭщɢɣ ɧɚɩɪɚɜɥɟɧɢɟ; + ɉɨɞɞɟɪɠɢɜɚɸщɢɣ ɩɟɪɟɩɢɫɤɭ Ключевые слова: ɤɚɥɢɤɫ[4]ɪɟɡɨɪɰɢɧɚɪɟɧɵ, ɬɟɪɦɨɝɪɚɜɢɦɟɬɪɢɹ, ɦɟɬɨɞɵ əɆɊ, ɬɪɚɧɫɩɨɪɬɚ/ɜɵɞɟɥɟɧɢɹ, ЖХȼД (ɠɢɞɤɨɫɬɧɚɹ ɯɪɨɦɚɬɨɝɪɚɮɢɹ ɜɵɫɨɤɨɝɨ ɞɚɜɥɟɧɢɹ), ɪɟɧɬɝɟɧɨɫɬɪɭɤɬɭɪɧɵɣ ɚɧɚɥɢɡ, ɦɟɬɨɞ Ʌɟɧɝɦɸɪɚ, ɷɥɟɤɬɪɨɯɢɦɢɱɟɫɤɢɣ ɦɟɬɨɞ. Ɋɟзюɦɟ Ʉɚɥɢɤɫ[4]ɪɟɡɨɪɰɢɧɚɪɟɧɵ, ɢɦɟɸщɢɟ ɥɢɩɨɮɢɥɶɧɭɸ ɢ ɚɦɢɧɨ ɮɭɧɤɰɢɢ, ɛɵɥɢ ɢɫɫɥɟɞɨɜɚɧɵ ɜ ɤɚɱɟɫɬɜɟ ɩɨɬɟɧɰɢɚɥɶɧɵɯ ɪɟɰɟɩɬɨɪɨɜ ɢɨɧɨɜ ɢ ɧɟɣɬɪɚɥɶɧɵɯ ɦɨɥɟɤɭɥ ɫ ɩɨɦɨщɶɸ ɬɟɪɦɨɝɪɚɜɢɦɟɬɪɢɱɟɫɤɨɝɨ ɦɟɬɨɞɚ, Ʉɉ/ɆАɉ əɆɊ, ɬɪɚɧɫɩɨɪɬɚ/ɜɵɞɟɥɟɧɢɹ, ɦɟɬɨɞɚ ЖХВД, ɪɟɧɬɝɟɧɨɜɫɤɨɝɨ, ɥɟɧɝɦɸɪɨɜɫɤɨɝɨ ɢ ɷɥɟɤɬɪɨɯɢɦɢɱɟɫɤɨɝɨ ɦɟɬɨɞɨɜ. Ɉɛɧɚɪɭɠɟɧɨ, ɱɬɨ ɤɚɥɢɤɫ[4]ɪɟɡɨɪɰɢɧɚɪɟɧɵ ɯɢɪɚɥɶɧɨɝɨ ɨɫɧɨɜɚɧɢɹ Ɇɚɧɧɢɯɚ, ɨɛɪɚɡɭɸщɢɟ ɩɥɟɧɤɭ Ʌɟɧɝɦɸɪɚ, ɞɢɮɮɟɪɟɧɰɢɪɭɸɬ ɚɦɢɧɨɤɢɫɥɨɬɵ ɜ ɜɨɞɧɨɣ ɩɨɞɮɚɡɟ. RECENT ADVANCES IN CALIX[4]RESORCINARENE CHEMISTRY © M. Pietraszkiewicz, 1 O. Pietraszkiewicz, 1 E. Uzig, 1 P. Prus, 1 Z. Brzózka, 2 K. Woźniak, 3 R. Bilewicz, 3 T. Borowiak, 4 and M. Mączyñski 4 1 Institute of Physical Chemistry Polish Academy of Sciences. 01224 Warsaw. Kasprzaka 44/52. Poland. E-mail: pietrasz@ichf.edu.pl 2 Department of Analytical Chemistry. Warsaw University of Technology. 00-664 Warsaw. Noakowskiego 3. Poland. 3 Department of Chemistry. University of Warsaw. 02093 Warsaw. Pasteura 1. Poland. 4 Department of Chemistry. A. Mickiewicz University. Grunwaldzka 6. 60-780 Poznan. Poland. Keywords: calix[4]resorcinarenes, thermogravimetry, CP/MAS NMR, transport/extraction, HPLC, X-ray, Langmuir, electrochemical methods. Abstract Calix[4]resorcinarenes bearing lipophilic and amino functions were investigated as potential receptors for ions and neutral molecules by means of thermogravimetric, CP/MAS NMR, transport/extraction, HPLC, X-ray, Langmuir, and electrochemical methods. Chiral Mannich-base calix[4]resorcinarenes forming Langmuir films were found to differentiate amino acids in water subphase. Introduction Calix[4]resorcinarenes deliver a versatile molecular platform for the elaboration of more complicated molecular host systems. Most of reactions with these compounds consists on electrophilic substitution of hydrogen atom between two hydroxyls, or substitutions on hydroxyl groups. One of the easiest reactions is the Mannich-type reaction with different amino components. We have dealt with a number of lipophilic C-tetraundecylcalix[4]resorcinarenes bearing four amino functions of different type, of which the general formula is presented below: R = C 11 H 23 OH OH HO R R R R HO HO HO OH OH X X X X Y OH OH HO HO O N O N O N O N R R R R Y Y Y N O CH 3 Ph R S 1 2 3 4 5 6 7 8 9 N O Y = N O N H NO 2 X = N N N CH 3 H OH CH 3 SO 2 CH 3 CH 10 Fig. 1. Structural formulas of investigated calix[4]resorcinarenes.