Supporting Information. Imatinib Intermediate as a Two in One Dual Channel Sensor for the
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supporting Information Imatinib Intermediate as a Two in One Dual Channel Sensor for the Recognition of Cu 2+ and I ions in Aqueous Media and its Practical Applications Samadhan R. Patil a, Jitendra P. Nandre a, Devising Jadhav a, Shilpa Bothra b, S. K. Sahoo b, Manisha Devi c, Chullikkattil P. Pradeep c, Pramod P. Mahulikar a *, Umesh D. Patil a * a School of Chemical Sciences, North Maharashtra University, P. B. No. 80, Jalgaon , (M.S.) INDIA, Tel: ; Fax: mahulikarpp@rediffmail.com (PPM), udpatil.nmu@gmail.com (UDP). b Department of Applied Chemistry, S. V. National Institute Technology, Surat , Gujrat, INDIA. c School of Basic Sciences, Indian Institute of Technology Mandi, Mandi, Himachal Pradesh, INDIA. S1
2 Synthesis of PPT-1 Synthesis of 2-Methyl-5-nitrophenyl-guanidine (1) [31] - The 20 g of 2-Methyl-5- nitroaniline (0.131 mol), g of cyanamide (0.263 mol) and 80 ml of ethanol were placed in a reaction flask. The reaction mixture was heated to 80 0 C and 18 ml of concentrated hydrochloric acid was slowly added dropwise within 80 minutes. The reaction mixture was stirred for 1 hour while maintaining the temperature at 80 0 C. 6 ml of concentrated hydrochloric acid was added dropwise and the reaction mixture was kept at 80 0 C for next 2 hours. The reaction mixture was cooled down to 60 0 C and 10 ml of 65% nitric acid (0.142 mol) was added dropwise and the mixture was left with stirring until it was cooled down to room temperature. The solid product was filtered off, washed with 50 ml of ethanol and dried in the air to afford l-(2-methyl-5-nitrophenyl) guanidine nitrate (yield 80 %), m.p.: C. 1 H-NMR (DMSO-d 6, 400 MHz): 2.36 (3H, s, CH 3 ), 7.40 (4H, m, 4NH), 7.59 (1H, d, J=8.2 Hz, 3-H), 8.05 (1H, d, J=2.5 Hz, 6-H), 8.19 (1H, dd, J=8.2 & 2.5 Hz, 4-H). Synthesis of 3-(Dimethyl amino)-1-(pyridin-3-yl) prop-2-en-1-one (2) [37]- In 250 ml one neck round bottomed flask, equipped with a mechanical stirrer and reflux condenser, the 3- acetyl pyridine (11 ml, 0.1 mol), N,N-dimethylformamide dimethylacetal (27 ml, 0.2 mol), and xylene (35 ml) were taken. The reaction mass washeated to C for about 20 h, and the methanol formed in the reaction was removed after every 4 h by distillation. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled down to room temperature. Hexane (20 ml) was added to the reaction mass and kept under stirring for 20 min without allowing the mass temperature to change more than 5 0 C. The resultant reactionmass was collected by filtration and washed with hexane, andthe crude product was recrystallized from xylene to give desired product as yellow crystals (Yield 90 %). m.p C. Synthesis of N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine (3) [31] - The condensation of 2-Methyl-5-nitrophenyl-guanidine (1, 1 mmole) and 3-(Dimethylamino)-1-(3- pyridinyl)-prop-2-en-1-one (2, 1 mmole) in n-butanol was achieved at reflux temperature. The S2
3 reaction was found to be complete after 9 hrs. After completion of the reaction, the reaction mass was diluted with distilled water, filtered, and dried to yield N-(5-nitro-2-methylphenyl)-4-(3- pyridinyl)-2-pyrimidineamine (3) with 65 % yield. m.p C; 1 H-NMR (DMSO-d 6, 400 MHz): 2.41 (3H, s, CH 3 ), 7.51 (3H, m, 3ArH), 7.93 (1H, dd, J=8.2 & 2.2 Hz, Ph-H), 8.42 (1H, d, J=7.9 Hz, PyH), 8.65 (1H, d, J=5.4 Hz, PymH), 8.74 (1H, dd, PyH), 8.72 (1H, d, J=2.2 Hz, PhH), 9.25 (1H, s, NH), 9.32 (1H, d, J=1.6 Hz, PyH). Fig. S1. LCMS of PPT-1. Fig. S2. 1 H-NMR of PPT-1. S3
4 Fig. S3. UV-Vis interference spectra of Cu 2+ ions by PPT-1 [2 ml, 3 х 10-5 M, in CH 3 CN:H 2 O (40:60, v/v)] in the presence of other metal ions (30 µl, 1 х 10-2 M, in H 2 O). Fig. S4. Jobs plot for determining 1:1 stoichiometry of PPT-1 [3 х 10-5 M, in CH 3 CN:H 2 O (40:60)] and Cu 2+ ions (3 х 10-5 M, in H 2 O). Fig. S5. Mole ratio plot/change in absorption spectra ( A) as a function of concentration of Cu 2+ ions. S4
5 Fig. S6. 1 H NMR titrations spectra of PPT-1 on addition of various ( ) equivalents of the copper perchlorate in CDCl 3. Fig. S7. HR-MS of PPT-1 in presence of Cu 2+. S5
6 Fig. S8. Linear fitting curve for LOD and LOQ determination of PPT-1 for Cu 2+. Fig. S9. UV/Vis-interference spectra/ Recognition of iodide ion by PPT-1[3 х 10-5 M, in CH 3 CN:H 2 O (40:60)] in the presence of other anions (1 х 10-2 M, in H 2 O). S6
7 Fig S10. 1 H NMR titrations spectra of PPT-1 on addition of various ( ) equivalents of the tetrabutylammonium iodide in CDCl 3. Fig. S11. HR-MS spectrum of PPT-1 in presence of tetrabutylammonium iodide. S7
8 Fig. S12. Jobs plot for determining stoichiometry (1:2) between PPT-1 [3 х 10-5 M, in CH 3 CN:H 2 O (40:60)] and iodide ions (3 х 10-5 M, in H 2 O). Fig. S13. Linear fitting curve for LOD and LOQ determination of PPT-1 for I. Table S1 A comparison of receptor PPT-1 with reported sensors. Research Group Selectivity and LOD value Ref. No. Sensitivity for U. D. Patil, et. al. Cu 2+ and I For Cu 2+ =0.54 µm This paper For I = 0.22 µm A. Jain, et. al. Only Cu J. Y. Miau, et. al. Only Cu µm 14 S. Dong, et. al. Only Cu nm 15 H. Cao, et. al. Only Cu B. Yan, et. al. Only Cu µm 17 S. Valiyaveettil, et. al. Only I - 19 J. Kang, et. al. Only I - 20 M. Haldimann, et. al. Only I 0.02 µm 21 S. Chandra, et. al. Only I 0.44 µm 23 K. Ito, et. al. Only I - 24 D. O. Jang, et. al. Only I 0.20 µm 25 S8
9 K. Ghosh, et. al. Only I - 26 R. Murugan, et. al. Only I - 27 M. Zhang, et. al. Only I 0.1 mm 28 K. Ghosh, et. al. Only I - 29 D.-G. Cho, et. al. Only I 30 µm 30 A. S. Kuwar, et. al. Only Cu P. Kaur, et. al. Hg 2+ and Cu 2+ For Cu 2+ =1.67 µm 39 P. Rashatasakhon, et. al. Only Cu nm 40 References not included in the manuscript: 39 P. Kaur, S. Kaur, K. Singh, P. R. Sharma and T. Kaur, Dalton Trans., 2011, 40, S. Sirilaksanapong, M. Sukwattanasinitt and P. Rashatasakhon, Chem. Commun., 2012, 48, S9
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