Zinc bis-[2-(tosylamino)benzylidene-n-alkyl(aryl, hetaryl)aminates], their using as luminophores

FIELD: organic chemistry.

SUBSTANCE: invention relates to novel compounds, namely zinc bis-[2-(tosylamino)benzylidene-N-alkyl(aryl, hetaryl)aminates] of the general formula (I): wherein Ts means tosyl; R means (C1-C6)-alkyl with exception isopropyl, (C1-C6)-alkyl-substituted phenyl, (C1-C6)-alkoxy-substituted phenyl with exception para- and ortho-methoxyphenyl, pyridyl, (C1-C6)-alkylpyridyl, or R + R form in common disulfidodialkyl group -(CH2)n-S-S-(CH2)n- wherein n = 1-3, but preferably to zinc bis-[2-(tosylamino)benzylidene-N-alkylidenemercaptoaminates] of the general formula (Ia): Compounds can be used for synthesis of light-radiating organic diode of white and visible light. Fluorescence can be observed in blue region of spectrum with fluorescence bands maximum at 428-496 nm. Quantum yields are 0.2-0.25.

EFFECT: valuable physical properties of compounds.

5 cl, 8 ex

 

The invention relates to new compounds, namely, bis[2-(tosylamide)benzyliden-N-alkyl(aryl,hetaryl)Aminata]zinc General formula

where Ts=tosyl, R=C1-C6alkyl, with the exception of isopropyl, C1-C6alkyl substituted phenyl, C1-C6alkoxy-substituted phenyl, with the exception of p - and o-methoxyphenyl, pyridyl, C1-C6alkylpyridine or R+R together form desulfotomaculum group - (CH2)n-S-S-(CH2)n-, where n=1-3. In the latter case, the compounds of General formula I accept the value - bis[2-(tosylamide)benzyliden-N-alkylaminocarbonyl]zinc General formula

The compounds I are luminescent properties.

The invention relates also to the use of bis[2-(tosylamide)benzyliden-N-alkyl(aryl,hetaryl)Aminatou]zinc the above General formula I, including compounds with R=isopropyl, phenyl, p - and o-methoxyphenyl, as phosphors emitting in the blue region of the spectrum that can be used to produce organic light-emitting diodes and white visible light.

The closest in performance and the achieved result is bis[(2-tosylaminophenyl)]-1,3-diamino-2-propanol zinc formula

showing fluorescent is voyta (band fluorescence λ =430 nm, quantum yield ϕ=0,14) /M.R.Bermejo, M.Vazquez, J.Sanmartin et. al. New J.Chem. 2002. V26. P.1365-1370/.

Object of the invention is the extension of a series of phosphors emitting in the blue region of the spectrum.

The technical result of the invention is: new connections in a series of bis[2-(tosylamide)benzyliden-N-alkyl(aryl,hetaryl)Aminatou]zinc exhibiting luminescent properties not described for this series, and new phosphors that emit in the blue region of the spectrum.

The technical result is achieved by compounds of General formula I and their use, including compound I with R=isopropyl, phenyl, p - and o-methoxyphenyl.

The invention satisfies the criterion of inventive step, since no known connections of a number of bis[2-(tosylamide)benzyliden-N-alkyl(aryl,hetaryl)Aminatou]zinc exhibiting luminescent properties. Among the compounds I are known compounds with R=isopropyl, phenyl, p - and o-methoxyphenyl (Adherence, Vahlensieck, Vaagan and other Coordination compounds of azomethines with o-totalminutes // Coord. Chemistry. 1977. V.3. No. 4. S-507). Fluorescent activity of the compounds is not described.

The method of obtaining the compounds of the first lies in the interaction azomethines 2-(tosylamide)benzaldehyde and substituted primary amines (III) dihydrate zinc acetate when heated.

The radical R in the compounds III is animal the above values of R=C 1-C6alkyl, C1-C6alkyl substituted phenyl, C1-C6alkoxy-substituted phenyl, pyridyl, C1-C6alkylpyridine or 2-(tosylamide)benzyliden-N-alkylsulphonyl

where n=1-3.

Below are examples of making connections.

Example 1. Bis[2-(tosylamide)benzyliden-N-phenylamino]zinc (R=C6H5).

To 2 mmole of 2-(tosylamide)benzylideneaniline (III, R=C6H5) in 20 ml of ethanol is added 1 mmol dihydrate zinc acetate in 10 ml of ethanol under heating for one hour. After neutralization formed in the reaction of acetic acid with ethanolic KOH, filtration of precipitated sludge, leaching and recrystallization from ethanol, to obtain yellow crystals of the target product with MP.>260°C. Found, %: C 62.96, H 4.38, N 7.45, S 8.45, Zn 8.75. For C40H34N4O4S2Zn, calculated, % 62.86; H 4.48, N 7.33, 8.39 S, Zn 8.55.

1H NMR, CDCl3that δ, ppm: 2.29 (6N, s, CH3), 6.82-7.38 (22N, mAr-H), 7.75 (4H, d,3J=8.04 Hz, CAr-H), 8.30 (2H, s, CH=N).

Compounds I in examples 2-7 are obtained analogously to example 1 using the corresponding azomethines III.

Example 2. Bis[2-(tosylamide)benzyliden-N-p-methoxybenzylamine]zinc (R=4-och3With6H4).

Yellow crystals, MP.>260°C. Found, %: C at 61.29, H 4.54, N 6.92, S 7.98, Zn 7.73. For 42H38N4O6S2Zn, calculated, % 61.20, H 4.65, N 6.80, S 7.78, Zn 7.93.

1H NMR, CDCl3that δ, ppm: 2.29 (6N, s, CH3), 3.78 (6N, s, och3) 6.77-7.37 (20N, mAr-H), 7.76 (4H, d,3J=8.17 Hz, CAr-H), 8.28 (2H, s, CH=N).

Example 3. Bis[2-(tosylamide)benzyliden-N-o-methoxybenzylamine]zinc (R=2-och3With6H4).

Yellow crystals, MP.>284-285°C. Found, %: C 61.32, H 4.72, N 6.75, S 7.82, Zn 7.81. For C42H38N4O6S2Zn, calculated, % 61.20, H 4.65, N 6.80, S 7.78, Zn 7.93.

1H NMR, CDCl3that δ, ppm: 2.25 (6N, s, CH3), 3.41 (6N, s, och3) 6.77-7.45 (20N, mAr-H), 7.95 (4H, d,3J=8.29 Hz, CAr-H), 8.37 (2H, s, CH=N).

Example 4. Bis[2-(tosylamide)benzyliden-N-p-ethoxyphenylurea]zinc (R=4-OS2H5With6H4).

Yellow crystals, MP.>260°C. Found, %: C 60.95, H 5.24, N 7.96, S 7.63, Zn 7.95. For C42H42N4O6S2Zn, calculated, % 60.90, H 5.11, N 6.76, S 7.74, Zn 7.89.

1H NMR, CDCl3that δ, ppm: 1.40 (6N, t3J=6.98 Hz, och2-CH3), 2.29 (6N, s, CH3), 3.98 (4H, kV,3J=6.97 Hz,Core2-CH3), 6.75-7.36 (20N, mAr-H), 7.76 (4H, d,3J=8.17 Hz, CAr-H), 8.27 (2H, s, CH=N).

Example 5. Bis[2-(tosylamide)benzyliden-N-ISO-propylamino]zinc (R=i-Pr).

Yellow crystals. MP.=222-223°C. Found, %: C, 59.12; H, 4.85; N, 8.17; S, 9.38; Zn, 9.32. For C34H34N4 4S2Zn. Calculated, %: C, 59.00; H, 4.95; N, 8.10; S, 9.29; Zn, 9.44.

1H NMR, CDCl3that δ, ppm: 1.45 (S, SN, t3J=6.14 Hz), 2.21 (6N, S. CH3), 4.14 (2H, quintet,3J=6.61 Hz, CH), 6.79-7.34 (M, mAr-H), 7.88 (4H, d,3J=8.24 Hz, CAr-H), 8.34 (2H, S, CH=N).

Example 6. Bis[2-(tosylamide)benzyliden-N-tert-butylamino]zinc(R=tert-C4H9).

Yellow crystals. MP.>260°C. Found, %: C, 59.73; H, 5.72; N, 7.86; S, 8.74; Zn, 9.23. For C36H42N4O4S2Zn. Calculated, %: C, 59.69; H, 5.35; N, 7.74; S, 8.85; Zn, 9.03.

1H NMR, CDCl3that δ, ppm: 1.58 (D, D.,3J=8.94 Hz,-CH3), 2.14 (6N, S., 2CH3), 6.68-7.32 (N, m, CAr-H), 7.65 (2H, d,3J=8.13 Hz, CAr-H), 8.44 (2H, S, CH=N).

Example 7. Bis[2-(tosylamide)benzyliden-N-2-pyridylamino]zinc(R=2-pyridyl).

Yellow crystals. T square>260°C. Found, %: C, 59.69; H, 4.11; N, 10.87; S, 8.49; Zn, 8.35. For C38H32N6O4S2Zn. Calculated, %: C, 59.57; H, 4.21; N, 10.97; S, 8.37; Zn, 8.53.

1H NMR, CDCl3that δ, ppm: 2.29 (6N, s, CH3), 6.87-7.86 (22 H, CAr-H), 8.33 (2H, d,3J=4.83 Hz, CAr-H), 9.21 (2H, S, CH=N).

Example 8. Bis[2-(tosylamide)benzyliden-N-ethylidenenorbornene] zinc, [R+R together form a (CH2)2-S-S-(CH2)2].

To a solution of 1 mmole of bis[2-(tosylamide)benzyliden-N-ethylidene sulfide] in 30 ml of ethanol is added a solution of 1 mmole dihydrate zinc acetate in 10 ml ethanolate heated for one hour. After neutralization of acetic acid with ethanolic KOH, filtration of precipitated sludge, leaching and recrystallization, to obtain white crystals with TPL 220-221°C. Yield 80%. Found, %: C 52.38, H 4.36, N 7.48, S 17.96, Zn 8.89. For C32H32N4O4S4Zn calculated, %: C 52.63, N 4. 42, N 7.62, S 17.56, Zn e.

1H NMR (CDCl3), δ (M. D.): 2.28 (6N, s, CH3), 2.67 (2H, t,3J=13.0 Hz, CH2), 3.19 (2H, t,3J=12.45 Hz, CH2), 3.67 (2H, d,3J=12.16 Hz, CH2), 6.82-7.38 (M, m, 8.02 (4H, d,3J=7.76 Hz, CHar), 8.18 (2H, s, CH=N).

The obtained compounds were investigated by standard methods, spectral-absorption and spectral-luminescent properties in a solution of acetonitrile at 293°K. the Maxima of long-wave absorption bands are in the area 350-390 nm. Absorption capacity is sufficiently high molar extinction coefficients in the maxima of the absorption bands are ε=10000-20000 lol-1see the Fluorescence of the complexes is observed in the blue region of the spectrum with maxima of the fluorescence bands at 428-496 nm. The efficiency of the fluorescence of some of them is also high, their quantum yields reach values of 0.2 to 0.25. For example, compounds Ia, where R=i-Pr, Ib, where R=tert-C4H9and Ic, where R+R together form a (CH2)2-S-S-(CH2)2have the following meanings:

*x the properties absorption: maximum absorption band λ (Ia)=270 and 351 nm, λ(Ib)=273 and 355 nm, λ(Ic)=274, 280 and 355 nm; molar extinction coefficient at the maximum absorption band ε(Ia)=18640 10590 and loli-1cm ε(Ib)=18650 and 10650 lol-1cm ε(Ic)=19050, 18500 and 10830 l mol-1cm;

*characteristics of fluorescence: the band maximum fluorescence λ(Ia)=428 nm, λ(Ib)=431 nm, λ(Ic)=433 nm; band maximum fluorescence excitation λ(Ia)=273 and 350 nm, λ(Ib)=274 and 355 nm, λ(Ic)=275 and 355 nm; quantum yield of fluorescence ϕ(Ia)=0,24, ϕ(Ib)=0,25, ϕ(Ic)=0,23.

1. Bis[2-(tosylamide)benzyliden-N-alkyl(aryl, hetaryl)Aminata]zinc General formula

where Ts is tosyl, R - C1-C6alkyl, with the exception of isopropyl, C1-C6alkyl substituted phenyl, C1-C6alkoxy-substituted phenyl, with the exception of p - and o-methoxyphenyl, pyridyl, C1-C6alkylpyridine or R+R together form desulfotomaculum group -(CH2)n-S-S-(CH2)n-, where n=1-3.

2. Bis[2-(tosylamide)benzyliden-N-alkyl(aryl,hetaryl)Aminat]zinc according to claim 1, where R is tert-butyl.

3. Bis[2-(tosylamide)benzyliden-N-alkyl(aryl,hetaryl)Aminat]zinc according to claim 1, where R+R together form desulfotomaculum group -(CH2)n-S-S-(CH2)n-, where n=1-3, bis[2-(tosylamide)benzyliden-N-alkylaminocarbonyl]zinc General formula

4. Bis [2-(tosylamide)benzyliden-N-allylmercaptan]zinc according to claim 3, where n=2 - bis[2-(tosylamide)benzyliden-N-ethylidenenorbornene]zinc.

5. Use as phosphors bis[2-(tosylamide)benzyliden-N-alkyl(aryl,hetaryl)Aminatou]zinc General formula

where Ts is tosyl, R1-C6alkyl, phenyl, C1-C6alkyl substituted phenyl, C1-C6alkoxy-substituted phenyl, pyridyl,1-C6alkylpyridine or R+R together form desulfotomaculum group -(CH2)n-S-S-(CH2)n-, where n=1-3.



 

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