Zinc complexes of 5-[2-hydroxy(tosylamino)benzylidene-amino]-2-(2-tosylaminophenyl)-1-alkylbenzimidazoles, having photoluminescent activity

FIELD: chemistry.

SUBSTANCE: invention relates to zinc complexes of 5-[2-hydroxy(tosylamino)benzylidene-amino]-2-(2-tosylaminophenyl)-1-alkylbenzimidazoles of general formula I , where R = alkyl C1-C6; X=O, ; .

EFFECT: compounds I exhibit luminescent properties and can be used as luminophores for producing organic light-emitting diodes emitting white and visible light.

18 ex

 

The invention relates to new compounds in the series of 5-benzylideneamino-2-(2-totalminutes)-1-alkylbenzenes, namely the zinc complexes of 5-[2-hydroxy(tosylamide)benzylideneamino]-2-(2-totalminutes)-1-alkylbenzenes General formula

where R=alkyl1-C6; X=O,

;

The compounds I are photoluminescent properties in the blue region of the spectrum and can be used as emitting layers when creating electroluminescent devices (organic light emitting diodes OLED) white and visible light.

Among zinc metallogenetic containing benzimidazole fragment and having a photoluminescent properties, known bis[2-(2-hydroxyphenyl)benzimidazole]zinc and 1-substituted formula II (A. S. Burlov, B. I. Kharisov, L. M. Blanko, L. I. Kuznetzova, D. A. Garnovskii, N. V. Volbushko, A. D. Garnovskii // Revista de la Sociedad Quimica de Mexico, 1999, V. 45, No 5, p. 143-148; A. S. Burlov, L. I. Kuznetsova, N. In. Wabuska, O. Y. Korshunov, A. D. garnovsky // GOH, 1998, I. 68, vol.3, S. 496-501; Y. H. Zhao, Z. M. Su, Y. Wang, X. R. Hao, K. Z. Shao // Acta Crystallogr., Sect. E: Struct. Rep. Online, 2006, V. 62, P. 2361; Y. P. Tong, B. H. Ye // Acta Crystallogr., Sect. E: Stuct. Rep. Online, 2004, V. 60, P. 1927; Y. P. Tong, S. L. Zheng, X. M. Chen // Eur. J. Inorg. Chem., 2005, P. 3734; Y. P. Tong, Y. W. Lin // J. Chem. Cryst. // 2008, V. 38, P. 613; Y. P. Tong, S. L. Zheng, X. M. Chen // J. Mol. Struct., 2007, V. 826, P. 104-112; H. Xu, Z. F. Xu, Z. Y. Yue, P. F. Yan, B. Wang, L. W. Jia, G. M. Li, W. B. Sun, J. W. Zhang // J. Phys. Chem. C, 208, V. 112, p 15517-15525)

,

where R=H, alkyl (C1-C6.

Complex compound II (R=H) lumines cent in the blue region of the spectrum (λ=460-480 nm) depending on the nature of the solvent with a quantum yield of φ=0.26 for the solid phase.

The closest structure is bis[2-(2-totalminutes)benzimidazole]zinc III (A. S. Burlov, L. I. Kuznetsova, N. In. Wabuska, O. Y. Korshunov, A. D. garnovsky // GOH, 1998, I. 68, vol.3, S. 496-501). However, its photoluminescent properties have not been studied.

Object of the invention is the expansion of the series photoluminescense zinc complexes emitting in the blue region of the spectrum, with high thermal stability and volatility.

The technical result of the invention are new compounds in a series of zinc complexes of 2-(2-totalminutes)benzimidazole, exhibiting luminescent properties with high quantum yields.

The technical result is achieved by compounds of General formula I.

The invention satisfies the criterion of inventive step, since it is not known impact structures of the compounds in the series of zinc complexes of 2-(2-totalminutes)benzimidazole to the manifestation of luminescent properties.

The method of obtaining the compounds I is in the interactions azomethines IV dihydrate zinc acetate when heated spirte. Bases obtained by condensation of 5-amino-2-(2-totalminutes)-1-alkylbenzenes (V) with salicylic aldehyde or 2-mozillamessaging.com in benzene or toluene. 5-Amino-2-(2-totalminutes)-1-alkylbenzenes (V) synthesized by reduction of 5-nitro-2-(2-totalminutes)-1-alkylbenzenes (VI) polysulfides in aqueous-alcoholic medium.

where R=alkyl1-C6; X=O,;

Below are examples of making connections.

Example 1. 5-Nitro-1-methyl-2-(2-totalminutes)benzimidazole (VIa, R=CH3; Ts=SO2C6H4CH3-R.).

To a solution of 6 mmol of 2-methylamino-5-nitroaniline in acetic acid is poured a solution of 12 mmol of copper acetate in water and a solution of 6 mmol of 2-tosylaminophenyl in glacial acetic acid. The reaction mixture is boiled, cooled, precipitated precipitate is filtered off, washed with water, dried. Then the copper salt in glacial acetic acid is treated with sodium thiosulfate solution in water. The precipitate is filtered off, washed with water and dried. Dissolved in chloroform and passed through a layer of aluminum oxide, the solvent is distilled off. Yield 72%. Recrystallized from DMF. Yellow crystals with TPL225-226°C. Found, %: C 59.65, H 4.34, N 13.35. For C21H18 N4O4's calculated, %: 59.70, H 4.29, N 13.26.

IR spectrum (in the solid phase): 3115, 3102, 3076, 3039, 2957, 2853, 1618, 1595, 1518, 1477, 1446, 1431, 1416, 1375, 1343, 1320, 1275, 1251, 1197, 1179, 1158, 1110, 1089, 1068, 1053, 1031, 951, 919, 892, 877, 869, 849, 816, 800, 772, 760, 740, 727, 710, 679, 656, 644, 612, 574, 557 cm-1.

1H NMR spectrum, DMSO-d6, δ, M. D.: 2.24 (3H, s,-CH3), 3.54 (3H, s, N-CH3), 7.00 (2H, d, J=7.8 Hz, CAr-H), 7.24 (2H, d, J=8.1 Hz, CAr-h), 7.35-7.44 (2H, m, CAr-H), 7.53-7.64 (2H, m, CAr-H), 7.84 (1H, d, J=9.0 Hz, CAr-H), 8.25 (1H, DD, J=9.0 Hz, J=2.1 Hz, CAr-H), 8.61 (1H, d, J=1.8 Hz, CAr-H), 10.08 (1H, s, NH).

Example 2. 5-Nitro-1-ethyl-2-(2-totalminutes)benzimidazole (VIb, R=C2H5; Ts=SO2C6H4CH3-R.).

Connection VIb obtained analogously to example 1 from 2-ethylamino-5-nitroaniline.

Recrystallized from DMF. Pale-yellow crystals with TPL202-203°C. Yield 59%. Found, %: C 60.44; N, 4.70; N, 12.92. For C22H20N4O4's calculated, %: C At 60.54; N, 4.62; N, 12.84

IR spectrum (in the solid phase): 3149, 2979, 2949, 1619, 1596, 1579, 1527, 1479, 1466, 1441, 1414, 1382, 1349, 1332, 1306, 1272, 1255, 1213, 1185, 1164, 1145, 1119, 1088, 1064, 1036, 982, 960, 951, 912, 875, 850, 821, 791, 756, 736, 722, 706, 680, 646, 619, 609, 578, 558 cm-1.

1H NMR,DMSO-d6, δ, M. D.: 1.23 (3H, T., J=7.2 Hz, CH2CH3), 2.27 (3H, s, CAr-CH3), 4.01 (2H, square, J=7.2 Hz, CH2CH3), 7.12 (2H, d, J=8.1 Hz, CAr-H), 7.35-7.54 (6N, m, CAr-H), 7.90 (1H, d, J=9.0 Hz, CAr-H), 8.24 (1H, D. D., J=8.9 Hz, J=1.3 Hz, CAr-H), 8.61 1H, D., J=1.5 Hz, CAr-H), 10.09 (1H, s, NH).

Example 3. 5-Nitro-1-propyl-2-(2-totalminutes)benzimidazole (VIc, R=C3H7; Ts=SO2C6H4CH3-R.).

Connection VIc obtained analogously to example 1 from 2-propylamino-5-nitroaniline.

Recrystallized from acetic acid. Pale-yellow crystals with TPL185-186°C. Yield 71%. Found, %: C 61.23; N, 5.01; N, 12.51. For C23H22N4O4's calculated, %: C 61.32; N, 4.92; N, 12.44

IR spectrum (in the solid phase): 3148, 3108, 2976, 2927, 2874, 2358, 1618, 1595, 1578, 1523, 1494, 1477, 1456, 1438, 1412, 1379, 1361, 1335, 1308, 1293, 1269, 1242, 1215, 1187, 1166, 1151, 1121, 1090, 1060, 1039, 1018, 948, 918, 899, 887, 821, 803, 773, 761, 740, 707, 682, 660, 649, 627, 616, 593, 577 cm-1.

1H NMR, DMSO-d6, δ, M. D.: 0.70 (3H, T., J=7.3 Hz, CH2CH2CH3), 1.56 (2H, square, J=7.4 Hz, CH2CH2CH3), 2.25 (3H, s, CAr-CH3), 3.97 (2H, T., J=7.5 Hz, CH2CH2CH3), 7.17 (2H, d, J=8.1 Hz, CAr-H), 7.32-7.55 (6N, m, CAr-H), 7.91 (1H, d, J=9.0 Hz, CAr-H), 8.23 (1H, D. D., J=8.9 Hz, J=2.2 Hz, CAr-H), 8.59 (1H, d, J=2.2 Hz, CAr-H), 10.07 (1H, s, NH).

Example 4. 5-Amino-1-methyl-2-(2-totalminutes)benzimidazole (Va, R=CH3; Ts=SO2C6H4CH3-R.).

To a solution of 13.5 mmol 5-nitro-1-methyl-2-(2-totalminutes)benzimidazole (VIa) in 50 ml of ethanol is added a solution of polysulfides made from 27 mmol deviations of sodium sulfide and 27 mmol of sulfur in 15 ml of water, and Ki is att for 4 hours. Alcoholic layer is separated, the solvent is distilled off. The residue is dissolved in 90 ml of 15%hydrochloric acid, filtered. The filtrate is cooled and treated with 22%ammonia solution to pH 7. The formed precipitate is filtered off, washed with water and dried. Recrystallized from ethanol. Cream-colored crystals with TPL172-173°C. Yield Of 87%. Found, %: C 64.17, H 5.21, N 14.36. For C21H20N4O2's calculated, %: C 64.27; H 5.14, N 14.28.

IR spectrum (in the solid phase): 3630, 3561, 3441, 3354, 3216, 3030, 2945, 2911, 2360, 1738, 1631, 1592, 1497, 1474, 1445, 1433, 1412, 1382, 1364, 1335, 1294, 1272, 1254, 1222, 1171, 1160, 1118, 1088, 1054, 1033, 1017, 956, 935, 917, 880, 844, 811, 790, 775, 731, 698, 675, 650, 614, 579, 558 cm-1.

1H NMR spectrum, DMSO-d6δ, M. D.: 2.22 (3H, s,-CH3), 3.33 (3H, s, N-CH3), 4.94 (2H, ush.s, NH2), 6.72 (1H, d, J=8.7 Hz, CAr-H), 6.87 (3H, d, J=8.4 Hz, CAr-H), 7.02 (2H, d, J=8.1 Hz, CAr-H), 7.26-7.33 (2H, m, CAr-H), 7.46-7.59 (3H, m, CAr-H), 10.60 (1H, ush.s, NH).

Example 5. 5-Amino-1-ethyl-2-(2-totalminutes)benzimidazole (Vb, R=C2H5; Ts=SO2C6CH4CH3-R.).

Compound Vb is obtained analogously to example 4 from 5-nitro-1-ethyl-2-(2-totalminutes)benzimidazole (VIb).

Recrystallized from ethanol. Cream-colored crystals with TPL163-164°C. Yield 74%. Found, %: C 64.91, H 5.58, N 13.84. For C22H22N4O2's calculated, %: C 65.00, H 5.45, N 13.78.

IR spectrum (in the solid phase): 3587, 3457, 3361, 3219, 2984, 2883, 1633, 1590, 1499, 476, 1439, 1417, 1395, 1382, 1338, 1288, 1273, 1252, 1217, 1185, 1165, 1153, 1115, 1090, 1060, 1035, 1018, 951, 915, 870, 847, 812, 785, 767, 756, 723, 684, 674, 647, 635, 616, 602, 579, 559 cm-1.

1H NMR spectrum, DMSO-d6, δ, M. D.: 1.18 (3H, t, J=6.9 Hz, CH2CH3), 2.23 (3H, s,-CH3), 3.74 (2H, K, J=6.8 Hz, CH2CH3), 5.01 (2H, ush.s, NH2), 6.72 (1H, d, J=8.7 Hz, CAr-H), 6.86 (1H, s, CAr-h), 6.94 (2H, d, J=7.8 Hz, CAr-H), 7.11 (2H, d, J=8.1 Hz, CAr-H), 7.29-7.32 (2H, m, CAr-H), 7.46-7.51 (2H, m, CAr-H), 7.57 (1H, d, J=8.1 Hz, CAr-H), 10.50 (1H, ush.s, NH).

Example 6. 5-Amino-1-propyl-2-(2-totalminutes)benzimidazole (Vc, R=C3H7; Ts=SO2C6H4CH3-R.).

Connection Vc obtained analogously to example 4 from 5-nitro-1-propyl-2-(2-totalminutes)benzimidazole (VIc).

Recrystallized from DMF. Cream-colored crystals with TPL140-141°C. Yield 80%. Found, %: C 65.59, H 5.82, N, 13.39. For C23H24N4O2's calculated, %: C 65.69, H 5.75, N 13.32.

IR spectrum (in the solid phase): 3651, 3462, 3440, 3374, 3058, 2969, 2937, 2878, 2366, 2335, 1629, 1593, 1498, 1471, 1443, 1414, 1393, 1359, 1335, 1314, 1272, 1247, 1210, 1186, 1164, 1152, 1118, 1087,1060, 1034, 1020, 951, 928, 900, 865, 848, 810, 793, 768, 730, 700, 676, 648, 612, 581 cm-1.

1H NMR spectrum, DMSO-d6, δ, M. D.: 0.82 (3H, t, J=7.4 Hz, CH2CH2CH3), 1.64 (2H, K, J=7.6 Hz, CH2CH2CH3), 2.27 (3H, s,-CH3), 3.67 (2H, t, J=7.8 Hz, CH2CH2CH3), 4.84 (2H, ush.s, NH2), 6.71 (1H, DD, J=8.6 Hz, J=1.6 Hz, CAr-H), 6.91-6.93 (3H, m, CAr-H), 7.5-7.25 (4H, m, CAr-H), 7.39 (1H, d, J=8.1 Hz, CAr-H), 7.42 (1H, d, J=7.8 Hz, CAr-H), 7.61 (1H, d, J=7.8 Hz, CAr-H), 10.15 (1H, ush.s, NH).

Example 7. 5-(2-Hydroxybenzylideneamino)-1-methyl-2-(2-totalminutes)benzimidazole (IVa, X=O; R=CH3; Ts=SO2C6H4CH3-R.).

To a solution of 1 mmole of 5-amino-1-methyl-2-(2-totalminutes)benzimidazole (Va) in 4 ml of benzene is poured a solution of 1 mmole of salicylic aldehyde in 3 ml of benzene and boiled for 2 hours. The solvent is then distilled off, the residue is treated with hexane. Recrystallized from DMF. The yellow crystals with TPL185-186°C. Yield 77%. Found, %: C 67.61, H 4.95, N 11.37. For C28H24N4O3's calculated, %: C 67.72, H 4.87, N 11.28.

IR spectrum (in the solid phase): 3113, 3066, 2953, 2325, 1934, 1907, 1868, 1791, 1749, 1674, 1627, 1605, 1573, 1516, 1498, 1478, 1456, 1434, 1406, 1375, 1324, 1281, 1271, 1220, 1201, 1181, 1161, 1141, 1114, 1089, 1055, 1031, 951, 916, 905, 879, 833, 806, 757, 735, 725, 704, 681, 650, 642, 630, 616, 608, 581 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 2.27 (3H, s,-CH3), 3.60 (3H, s, N-CH3), 6.96-7.03 (1H, m, CAr-H), 7.17 (2H, d, J=8.3 Hz, CAr-H), 7.42-7.47 (2H, m, CAr-H), 7.57-7.58 (2H, m, CAr-H), 7.73-7.75 (4H, m, CAr-H), 7.93 (1H,, J=0.9 Hz, CAr-H), 9.22 (1H, s, CH=N), 10.77 (1H, ush.s, NH), 13.48 (1H, s, OH).

Example 8. 5-(2-Hydroxybenzylideneamino)-1-ethyl-2-(2-totalminutes)benzimidazole (IVb, X=O; R=C2H5; Ts=SO2C6H4CH3-R.).

Compound IVb obtained similarly, PR is a measure 7 from 5-amino-1-ethyl-2-(2-totalminutes)benzimidazole (Vb).

Yellow crystals from DMF with TPL197-198°C. Yield 81%. Found, %: C 68.28, H 5.20, N, 11.05. For C29H26H4O3's calculated, %:C 68.22, H 5.13, N 10.97.

IR spectrum (in the solid phase): 3062, 2985, 2941, 1680, 1620, 1607, 1573, 1496, 1476, 1460, 1442, 1418, 1383, 1344, 1329, 1278, 1213, 1181, 1165, 1147, 1117, 1087, 1053, 1035, 1016, 980, 964, 951, 933, 906, 886, 858, 814, 766, 736, 706, 679, 651, 632, 617, 583 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 1.55 (3H, t, J=7.2 Hz, CH2CH3), 2.46 (3H, s,-CH3), 4.20 (2H, K, J=7.1 Hz, CH2CH3), 7.19-7.22 (4H, m, CAr-H), 7.45 (2H, d, J=8.2 Hz, CAr-H), 7.58-7.65 (2H, m, CAr-H), 7.74-7.84 (3H, m, CAr-H), 7.92-7.98 (3H, m, CAr-H), 8.13-8.15 (1H, m, CAr-H), 9.40 (1H, s, CH=N), 10.96 (1H, ush.s, NH), 13.66 (1H, s, OH).

Example 9. 5-(2-Hydroxybenzylideneamino)-1-propyl-2-(2-totalminutes)benzimidazole (IVc, X=O; R=C3H7; Ts=SO2C6H4CH3-R.).

Connection IVc obtained analogously to example 7 from 5-amino-1-propyl-2-(2-totalminutes)benzimidazole (Vc).

The yellow crystals from ethanol with TPL176-177°C. Yield 88%. Found, %: C At 68.59, H 5.46, N, 10.79. For C30H28N4O3's calculated, %: C 68.68; H 5.38, N 10.68.

IR spectrum (in the solid phase): 3065, 3035, 2974, 2958, 2872, 1623, 1608, 1573, 1493, 1474, 1458, 1443, 1416, 1380,1343, 1327, 1284, 1268, 1211, 1202, 1184, 1168, 1145, 1116, 1090, 1061, 1032, 1019, 964, 925, 906, 867, 852, 816, 802, 761, 734, 710, 679, 647, 628, 615, 598, 586, 559 cm-1.

1H NMR spectrum, DMSO-d6, δ, M. D.: 0.83 (3H, t, J=7.2 Hz, CH2CH2CH3), 1.67 (2H,K, J=7.5 Hz, CH2CH2CH3), 2.31 (3H, s,-CH3), 3.86 (2H, t, J=7.6 Hz, CH2CH2CH3), 6.91-7.00 (4H, m, CAr-H), 7.26-7.49 (7H, m, CAr-H), 7.61 (3H, d, J=8.4 Hz, CAr-H), 7.88 (1H, d, J=1.5 Hz, CAr-H), 9.08 (1H, s, CH=N), 10.57 (1H, s, NH), 13.31 (1H, s, OH).

Example 10. 5-(2-Tosylaminophenyl)-1-methyl-2-(2-totalminutes)benzimidazole (IVd, X=NSO2C6H4CH3-R; R=CH3; Ts=SO2C6H4CH3-R.).

To a solution of 2 mmol of 5-amino-1-methyl-2-(2-totalminutes)benzimidazole (Va) in 7 ml of toluene is poured a solution of 2 mmol of 2-tosylaminophenyl in 7 ml of toluene and boiled for 2 hours. Cool deposited precipitate is filtered off. Yield 91%. Recrystallized from DMF. Bright yellow crystals with TPL138-139°C. Found, %: C 64.60, H 4.89, N 10.95. For C35H31N5O4S2calculated, %: C 64.69, H 4.81, N, 10.78.

IR spectrum (in the solid phase): 3064, 2394, 1735, 1624, 1600, 1572, 1499, 1481, 1434, 1409, 1377, 1327, 1291, 1277, 1254, 1214, 1184, 1155, 1118, 1090, 1045, 1019, 936, 879, 811, 758, 734, 721, 705, 680, 657, 630, 617, 581 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 2.29 (3H, s,-CH3), 2.35 (3H, s,-CH3), 3.62 (3H, s, N-CH3), 6.97-6.98 (2H, m, CAr-H), 7.19-7.25 (3H, m, CAr-H), 7.39-7.44 (3H, m, CAr-H), 7.49-7.59 (1H, m, CAr-H), 7.57 (1H, DD, J=7.7 Hz, J=1.6 Hz, CAr-H), 7.86-7.89 (3H, m, CAr-H), 9.11 (1H, s, CH=N), 10.79 (1H, ush.s, NH), 13.27 (1H, s, NH).

Example 11. 5-(2-Tosylaminophenyl)-1-e is Il-2-(2-totalminutes)benzimidazole (IVe, X=NSO2C6H4CH3-p; R=C2H5; Ts=SO2C6H4CH3-R.).

Connection IVe obtained analogously to example 10 from 5-amino-1-ethyl-2-(2-totalminutes)benzimidazole (Vb).

Recrystallized from DMF crystals pale yellow color with TPL227-228°C. Yield 90%. Found, %: C 65.02, H 5.11, N, 10.64. For C36H33N5O4S2calculated, %:C 65.14, H 5.01, N, 10.55.

IR spectrum (in the solid phase): 3065, 2932, 2869, 1668, 1623, 1593, 1575, 1493, 1471, 1439, 1418, 1382, 1338, 1330, 1305, 1274, 1219, 1163, 1153, 1117, 1089, 1059, 1038, 1019, 966, 934, 919, 896, 886, 841, 807, 796, 763, 736, 703, 680, 659, 642, 631, 615, 581, 558 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 1.22 (3H, t, J=7.3 Hz, CH2CH3), 2.13 (3H, s,-CH3), 2.18 (3H, s,-CH3), 3.87 (2H, K, J=7.3 Hz, CH2CH3), 6.87-6.88 (2H, m, CAr-H), 7.05-7.07 (1H, m, CAr-H), 7.13 (2H, d, J=8.2 Hz, CAr-H), 7.23-7.27 (3H, m, CAr-H), 7.32-7.35 (1H, m, CAr-H), 7.40 (1H, DD, J=8.5 Hz, J=2.0 Hz, CAr-H), 7.43-7.46 (1H, m, CAr-H), 7.49-7.53 (2H, m, CAr-H), 7.59-7.60 (1H, m, CAr-H), 7.66-7.68 (2H, m, CAr-H), 7.70 (2H, d, J=8.3 Hz, CAr-H), 7.72-7.73 (1H, m, CAr-H), 8.94 (1H, s, CH=N), 10.61 (1H, ush.s, NH), 13.11 (1H, s, NH).

Example 12. 5-(2-Tosylaminophenyl)-1-propyl-2-(2-totalminutes)benzimidazole (IVf, X=NSO2C6H4CH3-R; R=C3H7; Ts=SO2C6H4CH3-R.).

Connection IVf obtained analogously to example 10 from 5-amino-1-ethyl-2-(2-tosylimines is)benzimidazole (Vc).

Recrystallized from ethanol, the crystals are yellow with TPL221-222°C. Yield Of 87%. Found, %: C 65.49, H 5.31, N, 10.42. For C37H35N5O4S2calculated, %: C 65.56, H 5.20, N, 10.33.

IR spectrum (in the solid phase): 3840, 2929, 2881, 2362, 2341, 1596, 1576, 1495, 1472, 1434, 1413, 1389, 1366, 1332, 1305, 1276, 1248, 1210, 1184, 1164, 1151, 1117, 1089, 1063, 1039, 1018, 962, 920, 903, 875, 837, 811, 763, 724, 704, 678, 661, 651, 639, 628, 612, 580 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 0.87 (3H, t, J=7.7 Hz, CH2CH2CH3), 1.75 (2H, K, J=7.7 Hz, CH2CH2CH3), 2.35 (3H, s,-CH3), 2.39 (3H, s,-CH3), 4.08 (2H, K, J=5.2 Hz, CH2CH2CH3), 7.15-7.17 (2H, m, CAr-H), 7.28 (1H, t, J=8.1 Hz, CAr-H), 7.42-7.46 (5H, m, CAr-H), 7.52-7.54 (1H, m, CAr-H), 7.58 (1H, DD, J=8.6 Hz, J=1.6 Hz, CAr-H), 7.61-7.64 (1H, m, CAr-H), 7.71 (1H, d, J=1.3 Hz, CAr-H), 7.73 (1H, s, CAr-H), 7.81 (1H, DD, J=8.3 Hz, J=0.6 Hz, CAr-H), 7.86-7.90 (5H, m, CAr-H), 9.11 (1H, s, CH=N), 10.72 (1H, ush.s, NH), 13.21 (1H, s, NH).

Example 13. Zinc complex of 5-(2-hydroxybenzylideneamino)-1-methyl-2-(2-totalminutes)benzimidazole (Ia, X=O; R=CH3; Ts=SO2C6H4CH3-R.).

To a solution of 1 mmole 5-(2-hydroxybenzylideneamino)-1-methyl-2-(2-totalminutes)benzimidazole (IVa) in 25 ml of tetrahydrofuran is poured a solution of 1 mmole dihydrate zinc acetate in 10 ml of ethanol is boiled for 2 hours, cooled, the precipitate filtered off, washed with ethanol and dried the. Recrystallized from DMF, pale yellow crystals with TPL>300°C. Yield 72%. Found, %: C 59.97, H 4.03, N 10.08, Zn 11.75. For C56H44N8O6S2Zn2calculated, %: C 60.06, H 3.96, N 10.01, Zn 11.68

IR spectrum (in the solid phase): 3062, 2929, 2360, 1628, 1608, 1594, 1564, 1514, 1497, 1482, 1472, 1457, 1426, 1396, 1331, 1295, 1280, 1263, 1241, 1218, 1185, 1138, 1108, 1086, 1061, 1037, 960, 947, 908, 884, 872, 836, 810, 771, 753, 737, 720, 696, 663, 645, 634, 617, 604, 589, 571 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 2.41 (6N, C, 2C-CH3), 3.60 (6N, s, 2N-CH3), 6.57 (2H, t, J=8.2 Hz, CAr-H), 6.95-7.07 (6N, m, CAr-H), 7.33-7.44 (10H, m, CAr-H), 7.51-7.63 (6N, m, CAr-H), 7.62-7.75 (4H, m, CAr-H), 8.16 (2H, d, J=8.2 Hz, CAr-H), 9.22 (2H, s, 2CH=N).

Compounds I in examples 14-18 obtained analogously to example 13.

Example 14. Zinc complex of 5-(2-hydroxybenzylideneamino)-1-ethyl-2-(2-totalminutes)benzimidazole (Ib, X=O; R=C2H5; Ts=SO2C6H4CH3-R.).

The yellow crystals from aqueous DMF with TPL>300°C. Yield 64%. Found, %: C 60.65, H 4.29, N 9.82, Zn 11.31. For C58H48N8O6S2Zn2calculated, %:C 60.68, H 4.22, N 9.76, Zn 11.39

IR spectrum (in the solid phase): 3005, 2971, 2938, 2921, 2360, 2343, 1738, 1668, 1608, 1594, 1573, 1533, 1479, 1463, 1443, 1428, 1380, 1348, 1328, 1300, 1282, 1243, 1217, 1206, 1143, 1087, 1063, 1043, 1020, 947, 907, 844, 813, 755, 730, 714, 665, 645, 634, 618, 606, 569 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 1.29 (6N, t, J=7.2 Hz, 2CH2CH3), 2.40 (6N, C, 2C-CH3 ), 4.45-4.47 (4H, m, 2CH2CH3), 6.57 (2H, t, J=6.8 Hz, CAr-H), 6.97-7.03 (6N, m, CAr-H), 7.34-7.45 (10H, m, CAr-H), 7.51 (2H, s, CAr-H), 7.56-7.81 (8H, m, CAr-H), 8.15 (2H, d, J=8.2 Hz, CAr-N), at 8.62 (2H, s, 2CH=N).

Example 15. Zinc complex of 5-(2-hydroxybenzylideneamino)-1-propyl-2-(2-totalminutes)benzimidazole (Ic, X=O; R=C3H7; Ts=SO2C6H4CH3-R.).

Recrystallized from DMF, bright yellow crystals with TPL>300°C. Yield 77%. Found, %: C 61.19, H 4.58, N 9.59, Zn 11.24. For C60H52N8O6S2Zn2calculated, %: C At 61.28, H 4.46, N 9.53, Zn 11.12.

IR spectrum (in the solid phase): 2964, 2970, 2842, 1676, 1666, 1604, 1591, 1567, 1525, 1509, 1476, 1460, 1439, 1406, 1391, 1351, 1322, 1308, 1295, 1283, 1241, 1189, 1148, 1137, 1087, 1069, 1049, 1034, 1004, 975, 947, 922, 905, 860, 842, 820, 809, 786, 768, 750, 719, 697, 656, 639, 605, 584, 568 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 0.68 (6N, t, J=7.4 Hz, 2CH2CH2CH3), 1.57 (4H, K, J=7.5 Hz, 2CH2CH2CH3), 2.46 (6N, C, 2C-CH3), 4.55 (4H, t, J=5.7 Hz, 2CH2CH2CH3), 6.64 (2H, t, J=7.4 Hz, CAr-H), 7.01-7.16 (6N, m, CAr-H), 7.40-7.52 (10H, m, CAr-H), 7.61-7.75 (8H, m, CAr-H), 8.18 (4H, d, J=8.4 Hz, CAr-H), 8.68 (2H, s, 2CH=N).

Example 16. Zinc complex of 5-(2-tosylaminophenyl)-1-methyl-2-(2-totalminutes)benzimidazole (Id, X=NSO2C6H4CH3-p; R=CH3; Ts=SO2C6H4CH3-R.).

Recrystallized from the same DMF, pale-yellow crystals with TPL>300°C. Yield 78%. Found, %: C 58.88, H 4.12, N 9.93, Zn 9.25. For C70H58N10O8S4Zn2calculated, %: C 59.95, H 4.10, N 9.82, Zn 9.17.

IR spectrum (in the solid phase): 3065, 3023, 2961, 2360, 2343, 1738, 1667, 1616, 1597, 1556, 1508. 1479, 1442, 1407, 1383, 1333, 1297, 1262, 1238, 1204, 1183, 1158, 1139, 1086, 1058, 1038, 1019, 949, 918, 897, 862, 834, 813, 801, 770, 755, 740, 714, 698, 661, 632, 617, 577, 567, 554 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 2.41 (6N, C, 2C-CH3), 2.42 (6N, C, 2C-CH3), 4.02 (6N, s, 2N-CH3), 6.85-6.87 (2H, m, CAr-H), 7.04-7.07 (2H, m, CAr-H), 7.31-7.34 (2H, m, CAr-H), 7.37-7.42 (10H, m, CAr-H), 7.48-7.49 (6N, m, CAr-H), 7.69 (2H, DD, J=7.8 Hz, J=1.7 Hz, CAr-H), 7.91 (2H, d, J=1.8 Hz, CAr-H), 8.01-8.03 (6N, m, CAr-H), 8.09 (2H, DD, J=9.0 Hz, J=0.6 Hz, CAr-H), 8.18-8.19 (4H, m, CAr-H), 8.43 (2H, s, 2CH=N).

Example 17. Zinc complex of 5-(2-tosylaminophenyl)-1-ethyl-2-(2-totalminutes)benzimidazole (Ie, X=NSO2C6H4CH3-R; R=C2H5; Ts=SO2C6H4CH3-R.).

Recrystallized from aqueous DMF, pale yellow crystals with TPL>300°C. Yield 94%. Found, %: C 59.49, H 4.37, N 9.78, Zn 10.04. For C72H62N10O8S4Zn2calculated, %: 59.46, H 4.30, N 9.63, Zn 8.89

IR spectrum (in the solid phase): 3064, 3019, 2971, 2923, 2359, 1738, 1667, 1624, 1614, 1597, 1556, 1478, 1450, 1441, 1427,1408, 1383, 1352, 1330, 1297, 1266, 1262, 1238, 1204, 1158, 1139, 1085, 1059, 1044, 1019, 948, 915, 896, 865, 847, 834, 812, 802, 787, 769, 756, 731, 715. 697, 662, 631,617, 600, 578, 567 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 1.43 (6N, t, J=7.3 Hz, 2CH2CH3), 2.40 (6N, C, 2C-CH3), 2.41 (6N, C, 2C-CH3), 4.50 (4H, K, J=7.6 Hz, 2CH2CH3), 6.86-6.89 (2H, m, CAr-H), 7.04-7.07 (2H, m, CAr-H), 7.30-7.33 (2H, m, CAr-H), 7.37-7.44 (8H, m, CAr-H), 7.46 (8H, d, J=8.5 Hz, CAr-H), 7.56 (2H, DD, J=8.6 Hz, J=1.9 Hz, CAr-H), 7.62 (2H, DD, J=7.8 Hz, J=1.7 Hz, CAr-H), 8.01-8.05 (8H, m, CAr-H), 8.14 (4H, d, J=8.2 Hz, CAr-H), 8.47 (2H, s, 2CH=N).

Example 18. Zinc complex of 5-(2-tosylaminophenyl)-1-propyl-2-(2-totalminutes)benzimidazole (If, X=NSO2C6H4CH3-R; R=C3H7; Ts=SO2C6H4CH3-R.).

Recrystallized from aqueous DMF, pale yellow crystals with TPL>300°C. Yield 79%. Found, %: C 59.87, H 4.59, N 9.58, Zn 8.96. For C74H66N10O8S4Zn2calculated, %: 59.96, H 4.49, N 9.45, Zn 8.82.

IR spectrum (in the solid phase): 3060, 2923, 2875, 2361, 2343, 1618, 1597, 1552, 1506, 1475, 1444, 1428, 1402, 1351, 1310, 1301, 1284, 1259, 1241, 1198, 1176, 1145, 1085, 1055, 1020, 1008, 973, 938, 915, 904, 888, 871, 850, 834, 812, 770, 756, 741, 719, 702, 668, 652, 634, 618, 592, 575, 567 cm-1.

1H NMR spectrum, DMF-d7, δ, M. D.: 0.74 (6N, t, J=7.6 Hz, 2CH2CH2CH3), 1.55 (4H, K, J=7.6 Hz, 2CH2CH2CH3), 2.27 (6N, C, 2C-CH3), 2.29 (6N, C, 2C-CH3), 4.34 (4H, K, J=7.8 Hz, 2CH2CH2CH3), 6.78 (2H, t, J=7.4 Hz, CAr-H), 6.90 (2H, t, J=7.6 Hz, CAr-H), 7.17 (2 is, t, J=7.9 Hz, CAr-H), 7.24-7.27 (6N, m, CAr-H), 7.29 (4H, d, J=7.9 Hz, CAr-H), 7.30 (2H, d, J=8.8 Hz, CAr-H), 7.35 (2H, DD, J=7.9 Hz, J=1.7 Hz, CAr-H), 7.41 (2H, d, J=7.8 Hz, CAr-H), 7.49 (2H, DD, J=7.7 Hz, J=1.6 Hz, CAr-H), 7.53 (2H, DD, J=8.6 Hz, J=1.9 Hz, CAr-H), 7.90 (6N, C, CAr-H), 7.97-7.99 (6N, m, CAr-H), 8.38 (2H, s, CH=N).

The obtained compounds were investigated by standard methods, spectral-absorption and spectral-luminescent properties in solution of dimethyl sulfoxide or acetonitrile, at T=293 K. the Maxima of long-wave absorption bands are in the area 330-389 nm in dimethyl sulfoxide and in the field 227-393 nm in acetonitrile.

The fluorescence of the complexes is observed in the blue region of the spectrum with maxima of the fluorescence bands at 474-493 nm. The efficiency of the fluorescence of some of them is also high, their quantum yields reach values of 0.07 and 0.35. For example, compounds Ia, where X=O; R=CH3; Ts=SO2C6H4CH3-R, Ib, where X=O; R=C2H5; Ts=SO2H4CH3-p, Ic, where X=O; R=C3H7; Ts=SO2C6H4CH3-R, Id, where X=NSO2C6H4CH3-R; R=CH3; Ts=SO2C6H4CH3-p, Ie, where X=NSO2C6H4CH3-R; R=C2H5; Ts=SO2C6H4CH3for example, If, where X=NSO2C6H4CH3-R; R=C3H7; Ts=SO2C 6H4CH3-R, have the following meanings:

absorption characteristics: maximum absorption bands in DMSO λ (Ia)=343 nm, λ (Ib)=338 nm, λ (Ic)=330 and 389 nm, λ (Id)=340 nm, λ (Ie)=336 nm, λ (If)=337 and 370 nm; in acetonitrile λ (Ic)=227, 276, 328 and 393 nm, λ (If)=280, 335 and 340 nm;

characteristics of fluorescence: the band maximum fluorescence λ (Ia)=493 nm, λ (Ib)=491 nm, λ (Ic)=493 nm, λ (Id)=478 nm, λ (Ie)=476 nm, λ (If)=474 nm; band maximum fluorescence excitation λ (Ia)=350 nm, λ (Ib)=360 nm, λ (Ic)=390 nm, λ (Id)=330 nm, λ (Ie)=360 nm, λ (If)=340 nm; quantum yield fluorescence φ (Ia)=0,07, φ (Ib)=0,18, φ (Ic)=0,35, φ (Id)=0,11 φ (Ie)=0,14, φ (If)=0,15.

Zinc complexes of 5-[2-hydroxy(tosylamide)benzylideneamino]-2-(2-totalminutes)-1-alkylbenzenes General formula

where R = alkyl1-C6; X=O,
;



 

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