Disodium 2,6-naphthalenedisulfonate

0.5g (1.5mmol) Pb(NO3)2 was dissolved in 10mL of distilled water taken in a beaker. A warm aqueous solution of disodium salt of 2, 6-naphthalene disulfonic acid, 0.48g (1.5mmol) was slowly added with stirring to aqueous solution of Pb(NO3)2. The white microcrystalline solid formed immediately which was filtered through fine filter paper, washed with water and air dried. The compound 2 was also soluble in DMSO but insoluble in water, methanol and other organic solvents. The compound was not decomposed up to 350C. Anal. Calc.: C, 23.46; H, 1.56; S, 12.52; Pb, 40.50. Found: C, 24.52; H, 1.48; S, 13.12; Pb, 42.08%. IR (neat, cm-1): 3355, 3056, 1630, 1576, 1140, 1086, 1022, 896, 813, 657, 479. 1H NMR (DMSO-d6, 400MHz) delta 8.19 (d, 2H), 8.00 (d, 2H) 7.78 (dd, 2H). 13C NMR (DMSO-d6, 100MHz), delta 149.2, 147.8, 146.0, 132.0, 128.0, 125.2, 124.2, 123.7.0.5g (1.5mmol) Pb(NO3)2 was dissolved in 10mL of distilled water taken in a beaker. A warm aqueous solution of disodium salt of 2, 6-naphthalene disulfonic acid, 0.48g (1.5mmol) was slowly added with stirring to aqueous solution of Pb(NO3)2. The white microcrystalline solid formed immediately which was filtered through fine filter paper, washed with water and air dried. The compound 2 was also soluble in DMSO but insoluble in water, methanol and other organic solvents. The compound was not decomposed up to 350C. Anal. Calc.: C, 23.46; H, 1.56; S, 12.52; Pb, 40.50. Found: C, 24.52; H, 1.48; S, 13.12; Pb, 42.08%. IR (neat, cm-1): 3355, 3056, 1630, 1576, 1140, 1086, 1022, 896, 813, 657, 479. 1H NMR (DMSO-d6, 400MHz) delta 8.19 (d, 2H), 8.00 (d, 2H) 7.78 (dd, 2H). 13C NMR (DMSO-d6, 100MHz), delta 149.2, 147.8, 146.0, 132.0, 128.0, 125.2, 124.2, 123.7.0.5g (3mmol) 11 AgNO3 was dissolved in 10mL of distilled 12 water taken in a beaker. A warm aqueous solution of 13 disodium salt of 2, 6-naphthalenedisulfonic acid, 0.49g (1.5mmol) was slowly added with stirring to aqueous solution of AgNO3. A white precipitates formed immediately which was filtered through fine filter paper, washed with water and dried in oven at 40C. The compound 1 was freely soluble in 14 DMSO but insoluble in water, methanol and other organic solvents. The compound 1 does not decompose up to 350C. Anal. Calc.: C, 23.91; H, 1.19; S, 12.75; Ag, 42.91. Found: C, 23.62; H, 1.28; S, 13.02; Ag, 42.68%. IR (neat, cm-1): 3081, 1625, 1587, 1123, 1079, 1006, 827, 650, 478. 1H NMR (DMSO-d6, 400MHz) delta 8.15 (d, 2H), 7.94 (d, 2H), 7.75 (dd, 2H), 13C NMR (DMSO-d6, 100MHz), delta 145.8, 131.9, 128.0, 124.25, 123.8General procedure: All three polymers were synthesized by the same method (Scheme S1, Supporting Information), as follows: a mixture of M(CH3COO)2 (M = Cd(1), Cd(2), and Cu(3), 0.1 mmol), naphthalenedisulfonate ligand (0.1 mmol), imidazole ligand (0.1 mmol) and H2O (10 mL) was adjusted to the special pH values with HNO3 (1 M) and NaOH (1 M) (the pH values of 4 for 1, and 4.5 for 2 and 3, respectively), stirred for 0.5 h, and then transferred and was sealed in a 25 mL Teflon-lined stainless steel vessel and heated at 160C for 3 days. Cooling the vessel to room temperature at a rate of 5C h-1 afforded crystals of 1-3 suitable for a single crystal X-ray diffraction.General procedure: All three polymers were synthesized by the same method (Scheme S1, Supporting Information), as follows: a mixture of M(CH3COO)2 (M = Cd(1), Cd(2), and Cu(3), 0.1 mmol), naphthalenedisulfonate ligand (0.1 mmol), imidazole ligand (0.1 mmol) and H2O (10 mL) was adjusted to the special pH values with HNO3 (1 M) and NaOH (1 M) (the pH values of 4 for 1, and 4.5 for 2 and 3, respectively), stirred for 0.5 h, and then transferred and was sealed in a 25 mL Teflon-lined stainless steel vessel and heated at 160C for 3 days. Cooling the vessel to room temperature at a rate of 5C h-1 afforded crystals of 1-3 suitable for a single crystal X-ray diffraction. For 1, yield: 0.497 g, 78% based on Cd. Anal. Calc for C24H20CdN4O6S2: C, 45.25; H, 3.16; N, 8.80. Found: C, 45.39; H, 3.24; N, 8.92%. IR (KBr, cm-1): 2940 m, 2843 m, 1620 w, 1570 m, 1498 m, 1433 m, 1326 m, 1199 s, 1064 s, 1030 s, 987 w, 930 m, 856 m, 831 m, 772 m, 755 m, 718 s, 662 s.12 parts of dye intermediate 2, 4.16 parts of Na2NDS (0.031 g, 0.25 mmol), CB[6] (0.05 g, 0.05 mmol), DMF (1mL) and H2O (3 mL) in a sealed Teflon-lined stainless steel container(10 mL), which was heated at 120 C for 48 h, and then cooled to roomtemperature at 4 oC·h-1. After cooling down to room temperature, colorless crystals of 1 was collected by filtration and washed with H2Othree times. Anal. calcd for 1 (C46 H42 N24 O18 S2): C, 43.06; H, 3.30;N, 26.20%. Found: C, 42.98; H, 3.36; N, 26.23%.

Used as dye intermediate and concrete reinforcing agent.

Molecular Weight:332.3
Hydrogen Bond Acceptor Count:6
Exact Mass:331.94011882
Monoisotopic Mass:331.94011882
Topological Polar Surface Area:131
Heavy Atom Count:20
Complexity:423
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes