REFERENCES
- Asfari , Z. , Bohmer , V. , Harrowfield , J. and Vicens , J. 2001 . Calixarenes 2001 , Netherlands : Kluver .
- Vicens , J. and Harrofield , J. 2007 . Calixarenes in Nanoworld , Netherlands : Springer .
- Koifman , O. I. , Mamardashvili , N. Z. and Antipin , I. S. 2006 . Synthetic Receptors Based on Porphyrines and their Conjugates with Calix[4]arenes , Moscow : Nauka . (in Russian)
- Konovalov , A. I. and Antipin , I. S. 2008 . Mendeleev Commun , 18 : 229 – 237 .
- Voloshin , Y. Z. , Kostromina , N. A. and Krämer , R. 2002 . Clathrochelates: Synthesis, Structure and Properties , Amsterdam : Elsevier .
- Voloshin , Y. Z. , Zavodnik , V. E. , Varzatskii , O. A. , Belsky , V. K. , Palchik , A. V. , Strizhakova , N. G. , Vorontsov , I. I. and Antipin , M. Y. 2002 . J. Chem. Soc., Dalton Trans. , : 1193 – 1202 .
- Compound 1: (a) Synthesis of thioaceto-derivative. The terminal diallyl-containing calixarene, thioacetic acid (1 : 4) and a catalytic amount of AIBN in absolute toluene was refluxed for 5 h under argon . Then the solvent was evaporated to dryness and the solid residue was recrystallized from methanol (yield: 83%). 1H NMR (CDCl3, δ, ppm): 7.98 (s, 2H, OH), 7.05 (d, 4H, ArH), 6.91 (d, 4H, ArH), 6.75 (t, 4H, ArH), 6.65 (m, 2H, ArH), 4.23 (d, 2H, ArOCH2Ar), 3.43 (d, 4H, ArOCH2Ar), 4.12 (m, 4H, ArOCH2), 2.92 (m, 4H, CH2S), 2.31 (m, 4H, CH2CH2CH2–S), 2.38 (s, 6H, CH3). MALDI TOF, m/z (p-NA) 656 [M] +, 679 [M + Na+] +, 695 [M + K+] +; (b) Synthesis of mercaptopropoxycalixarene 1. o-Disubstituted thioacetopropoxycalixarene (0.46 mmol) with terminal reactive groups was dissolved/suspended in hydrazine hydrate (20 mL). The reaction mixture was refluxed for 21 h under argon. Then, the reaction mixture was filtered, the precipitate was washed with 2M HCl, water, methanol and hexane. Yield of: 62%.1H NMR (CDCl3, δ, ppm): 8.05 (s, 2H, OH), 7.06 (d, 4H, ArH), −1; ν (SH) = 2550 cm−1. MALDI TOF, m/z (p-NA, DHB): 571.31 [M] +, 595.34 [M + Na+] +, 611.56 [M +K+] +
- Compound 3: Conventional heating: Compounds 1 and 2 and, triethylamine in the molar ratio 1:1:1 were dissolved in dichloromethane. The reaction mixture was stirred at room temperature for 6 h and at 30°C for 8 h . Then, DMF was added and the reaction mixture was heated at 80°C for 24 h under argon. The product 3 was isolated by a column chromatography (eluent: hexane–acetone). Yield of 3: 60%. The reaction mixture was also heated using microwave oven for 1.5 h in dichloromethane. Yield of 3: 67%. 1H NMR (Bruker AVANCE-600, CDCl3, δ, ppm, J, Hz): 7.78 (s, 2H, OH), 7.01 (d, 4H, ArH), 6.87 (d, 4H, ArH), 6.70 (m, 2H, ArH), 6.63 (m, 2H, ArH), 4.15 (d, 4H, ArCH2Ar), 3.34 (d, 4H, ArCH2Ar), 4.06 (m, 4H, ArOCH2), 3.76 (m, 4H, CH2S), 2.42 (m, 4H, CH2CH2CH2–S). MALDI TOF (Ultraflex Bruker), m/z (p-NA): 1245 [M] +, 1269 [M + Na+] +, 1284 [M + K+] +. m/z (DHB) in 1269 [M + Na+] +, 1284 [M + K+] +