<p> SUPPLEMENTARY INFORMATION</p><p>A study of interfacial adsorption isotherm at divided interface for</p><p> novel macrocycles in solvent extraction</p><p>Halil Zeki Gök a ,, Hasan Demir b</p><p> a Department of Chemistry, Osmaniye Korkut Ata University, 80000 Osmaniye, Turkey</p><p> b Department of Chemical Engineering, Osmaniye Korkut Ata University, 80000 Osmaniye, Turkey</p><p>1. Experimental</p><p>1.1. Materials and Equipment</p><p> Corresponding author. Tel.: + 90 (328)-827 1000x2539; fax: +90 (328)-825 0097; e-mail: [email protected], Department of Chemistry, Faculty of Arts and Sciences, Osmaniye Korkut Ata University, 80000, Osmaniye, Turkey N,N'-(2,2'-(4,5-dicyano-1,2-phenylene)bis(sulfanediyl)bis(2,1-phenylene))bis(2- chloroacet-amide) 1 was prepared according to the literature report [1]. Macrocycles 3 and 5 were prepared according to the literature reports [1, 2]. All reagents and solvents were reagent grade quality and were obtained from commercial suppliers. For synthesis, all solvents were dried and purified as described by Perrin and Armarego [3]. Demineralized water was used in extraction experiments. FTIR spectra were measured on a Perkin Elmer Spectrum 65 spectrometer in KBr pellets. 1H and 13C NMR spectra were recorded on a Varian Mercury 400</p><p>MHz spectrometer in CDCl3 and DMSO-d6 (99.9%). Mass spectra were measured on a</p><p>Micromass Quatro LC/ULTIMA LC-MS/MS spectrometer. Optical spectra were recorded in the UV-Vis region with a PG-T80+ spectrophotometer in 1 cm path length cuvettes at room temperature. The elemental analyses were obtained with a LECO Elemental Analyzer (CHNS</p><p>0932) spectrophotometer. The melting points were determined with an electrothermal apparatus and are reported without correction. In solvent extraction experiment Selecta type shaker with thermostat was used. 11 6,3</p><p>11 0</p><p>10 5 562,18</p><p>477,79 10 0 3051,91 950,50 498,91</p><p>710,13 526,46 95</p><p>2923,06 1058,79 90 1159,16 1032,03 873,11 1133,82 917,96 3285,62 1107,49 85 659,40 1226,68 2234,99 1264,34 80 1383,96 1197,06 1345,48 75 1460,71 % T 70</p><p>65</p><p>60 1295,80</p><p>55 764,67</p><p>1577,46 1433,59 50 O</p><p>NC S N S 45 H S H 40 NC S N S 1682,34</p><p>O 35 1513,38</p><p>30 ,7 400 0,0 360 0 32 00 28 00 2 400 2 000 1 800 1 600 14 00 12 00 10 00 80 0 60 0 450 ,0 cm-1</p><p>Figure S1. The FT-IR spectrum of macrocyclic ligand 2</p><p>12 9 ,1</p><p>1 2 5</p><p>1 2 0 569,91 475,75 1 1 5 497,88</p><p>529,97 1 1 0 2989,23 2349,33</p><p>1 0 5 3067,67 1737,82 2956,24 951,68 712,35 1 0 0 2919,18 872,96 667,32 3251,78 2860,28 1055,11 917,91 1161,41 1033,87 95 1199,00 1346,48 2227,54 1374,22 1266,91 90 1455,63 1235,04 1220,97 85 1103,05 % T 80 1295,22</p><p>1435,06 763,13 75 1577,55</p><p>70</p><p>65 O 1691,02</p><p>60 NC S N S 1517,70 H 55 O H 50 NC S N S</p><p>45 O</p><p>40 3 7 ,2 4 0 0 0,0 36 0 0 3 2 00 2 8 00 2 4 0 0 2 0 0 0 1 8 00 1 6 00 1 4 0 0 1 2 0 0 1 0 00 8 0 0 6 0 0 4 5 0 ,0 c m- 1</p><p>Figure S2. The FT-IR spectrum of macrocyclic ligand 3 89 ,5 88</p><p>86</p><p>84 921,95 82 888,32 528,00 1034,83 80</p><p>78 1108,65 1383,29 76 3275,93 1345,99</p><p>74 2230,55</p><p>1221,30 72 2856,12 70</p><p>68 % T 66 1456,53 1297,35 64</p><p>62 2926,48 60 757,93 58 1578,55</p><p>O 1435,06 56 1688,81 54 NC S N S H 52 H NC S N S 50</p><p>O 1513,84 48</p><p>45 ,7 400 0,0 360 0 32 00 28 00 2 400 2 000 1 800 1 600 14 00 12 00 10 00 80 0 60 0 450 ,0 cm-1</p><p>Figure S3. The FT-IR spectrum of macrocyclic ligand 4 Date: 20 Aralýk 2011 Salý</p><p>88,0</p><p>85</p><p>80 950,00 479,09</p><p>1060,12 502,88 2915,67 1032,55 75 1161,13 1105,78 879,41 673,10 527,48 918,96 1261,38</p><p>70 1380,36 3253,86 1223,31</p><p>65 2232,25 1347,85</p><p>758,36 %T 60 1454,72</p><p>55 1299,34 1568,11 O 50 NC S N S H H 1435,21 45 NC S N S 1578,94</p><p>O 40 1680,12</p><p>35 1515,01 33,0 4000,0 3000 2000 1500 1000 450,0 cm-1</p><p>Figure S4. The FT-IR spectrum of macrocyclic ligand 5 Date: 20 Aralýk 2011 Salý</p><p>89,5 88</p><p>86</p><p>84 542,71 480,06 82 470,36 500,82 80 615,90 693,24</p><p>78 525,97 3079,56 918,48 76 2920,84 1035,46</p><p>74 889,24 3316,78 72 1158,78 2228,75 1261,75 1104,12 70 1384,80 %T 68 1347,01 66 1213,52</p><p>64 1452,62</p><p>62 1290,59</p><p>60 O 1576,87 1565,11 756,57 58 NC S N S H 56 H 1434,16 NC S N S 54 1688,58 52 O 1514,53 50 48,8 4000,0 3000 2000 1500 1000 450,0 cm-1</p><p>Figure S5. The FT-IR spectrum of macrocyclic ligand 6</p><p>O</p><p>NC S N S H S H NC S N S</p><p>O</p><p>7.650 7.600 7.550 7.500 7.450 7.400 7.350 7.300 ppm (t1) 1 1 1 1 0 . . . . . 0 2 0 8 9 6 7 7 2 4 1 1 1 0 1 0 2 4 ...... 0 0 1 9 6 8 1 5 0 0 4 8 6 5 8 3</p><p>10.0 5.0 ppm (t1)</p><p>1 Figure S6. The H-NMR spectrum of macrocyclic ligand 2 in CDCl3. O</p><p>NC S N S H O H NC S N S</p><p>O 1 0 1 1 1 0 2 2 2 ...... 0 9 0 0 4 8 1 1 0 0 6 5 2 8 5 3 2 9</p><p>5.0 ppm (t1)</p><p>1 Figure S7. The H-NMR spectrum of macrocyclic ligand 3 in CDCl3.</p><p>O</p><p>NC S N S H H NC S N S</p><p>O</p><p>1.700 1.650 1.600 1.550 1.500 ppm (t1) 1 1 1 1 1 0 2 2 3 1 ...... 0 0 5 0 6 8 0 2 3 4 0 9 2 4 2 2 5 8 1 7</p><p>10.0 5.0 ppm (t1)</p><p>1 Figure S8. The H-NMR spectrum of macrocyclic ligand 4 in CDCl3. O</p><p>NC S N S H H NC S N S</p><p>O</p><p>1.9001.8751.8501.8251.8001.7751.7501.7251.700 3.5003.4503.4003.3503.3003.2503.200 ppm (t1) ppm (t1)</p><p>10.00 9.50 9.00 8.50 8.00 7.50 7.00 6.50 6.00 5.50 5.00 4.50 4.00 3.50 3.00 2.50 2.00 1.50 1.00 ppm (t1)</p><p>1 Figure S9. The H-NMR spectrum of macrocyclic ligand 5 in DMSO-d6.</p><p>O</p><p>NC S N S H H NC S N S</p><p>O 1 1 2 1 0 2 2 ...... 0 0 3 2 9 5 2 0 7 8 5 1 2 0</p><p>5.0 0.0 ppm (t1)</p><p>1 Figure S10. The H-NMR spectrum of macrocyclic ligand 6 in CDCl3 O</p><p>NC S N S H S H NC S N S</p><p>O</p><p>150 100 50 0 ppm (t1)</p><p>13 Figure S11. The C-NMR(APT) spectrum of macrocyclic ligand 2 in CDCl3</p><p>O</p><p>NC S N S H O H NC S N S</p><p>O</p><p>150 100 50 0 ppm (t1)</p><p>13 Figure S12. The C-NMR(APT) spectrum of macrocyclic ligand 3 in CDCl3 O</p><p>NC S N S H H NC S N S</p><p>O</p><p>150 100 50 0 ppm (t1)</p><p>13 Figure S13. The C-NMR(APT) spectrum of macrocyclic ligand 4 in CDCl3</p><p>O</p><p>NC S N S H H NC S N S</p><p>O</p><p>150 100 50 0 ppm (t1)</p><p>13 Figure S14. The C-NMR(APT) spectrum of macrocyclic ligand 5 in CDCl3 O</p><p>NC S N S H H NC S N S</p><p>O</p><p>150 100 50 0 ppm (t1)</p><p>13 Figure S15. The C-NMR(APT) spectrum of macrocyclic ligand 6 in CDCl3 References </p><p>[1] H.Z. Gök, B. Farsak, Synthesis, characterisation and aggregation properties of novel</p><p> metal-free and metallophthalocyanines containing four 21-membered oxatetrathiadiaza</p><p> macrocycles, J. Organomet. Chem. 735 (2013) 65-71. </p><p>[2] H.Z. Gök, B. Farsak, Synthesis and spectral properties of novel metal-free and</p><p> metallophthalocyanines bearing four 19-membered tetrathiadiaza macrocycles, J. Mol.</p><p>Struct. 1054-1055 (2013) 25-31.</p><p>[3] D.D. Perrin, W.L.F. Armarego, Purification of Laboratory Chemicals. 2nd ed.,</p><p>Pergamon Press, Oxford, 1989.</p><p>Appendix A. Supplementary material Additional data associated with this article are given in Online Resource 1</p>