Zinc bis[2-(tosylamino)benzylidene-1n-alkyliminates] having luminescent activity

FIELD: chemistry.

SUBSTANCE: invention relates to zinc bis[2-(tosylamino)benzylidene-N-alkyliminates] of general formula , where Ts = tosyl, R=C7-C18 alkyl.

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

3 cl, 2 ex

 

The invention relates to new compounds in a series of bis[2-(tosylamide)benzyliden-N-alkylamines]zinc, namely, bis[2-(tosylamide)benzyliden-N-alkylamines]zinc General formula

where Ts=tosyl, R=C7-C18alkyl. The compounds I are luminescent properties in the blue region of the spectrum and can be used as phosphors to obtain organic light-emitting diodes and white visible light.

Known bis[(2-tosylaminophenyl)]-1,3-diamino-2-propanol zinc formula

exhibiting luminescent properties (band fluorescence λ=430 nm, quantum yield φ=0,14) /M.R.Bermejo, M.Vazquez, J.Sanmartin et. al. New J. Chem. 2002. V.26. P.1365-1370/.

The closest in performance and the achieved result is bis[2-(tosylamide)benzyliden-N-alkylamine]zinc General formula

where Ts=tosyl, R=C1-C6alkyl, and other Compounds III exhibit fluorescent properties. However, these properties are not sufficiently high (patent RU №2295527, C07F 3/06, 2007).

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 are new compounds in a series of bis[2-(tosylamide)benzyliden-N-alkylamino]zinc exhibiting fluorescent properties, and is also the connection with a higher quantum yield.

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

The invention satisfies the criterion of inventive step, since it is unknown the effect of changing the length of the alkyl radical in the compounds of series of bis[2-(tosylamide)benzyliden-N-alkylamino]zinc on the change in the value of the quantum yield.

The method of obtaining the compounds I is electrochemical synthesis based on the anodic dissolution of zinc in oxidation state zero in an alcohol solution of h. The cathode used platinum, conductive additive [Et4N]ClO4(tetraethylammonium perchlorate).

The cathode (Pt): 2LH+2e→2L-+H2

The anode (Zn0): Zn-2e→Zn2+

Solution: 2L-+Zn2+→ZnL2(I).

Below are examples of making connections.

Example 1. Bis[2-(tosylamide)benzyliden-N-heptylamine]zinc (R=C7H15)

In an electrochemical cell with a platinum cathode and a zinc anode was placed a solution of 0.75 g of 2-(N-tosylamide)benzylparaben in 20 ml of methanol, add as conductive additives 0.01 g [Et4N]ClO4. The electrosynthesis is carried out at current 40 mA and a voltage of 20 V for one hour at room temperature. The precipitation of the complex is filtered off and recrystallized from a mixture of chloroform: methanol (1:2). Get white crystals with TPL264-265 is C. Yield 0.7 g (87%). Found, %: C 64.88, H 7.15, N 7.32, Zn 8.35. For C42H54N4O4S2Zn calculated, %: C 64.98, H 7.01, N 7.21, Zn 8.42.

1H NMR spectrum, CDCl3, δ, ppm 0.79 (6N, t, J=7.1 Hz, CH2CH3), 1.02-1.27 (M, m, CH2), 1.45 (2H, m, CH2), 2.26 (6N, s, CH3), 3.34-3.88 (2H, m, CH2), 4.37-4.39 (2H, m, CH2), 6.80 (2H, J=7.1 Hz, CArH), 7.05 (4H, d, J=8.2 Hz, CArH), 7.14-7.24 (4H, m, CArH), 7.49 (2H, d, J=8.4 Hz, CArH) 8.04 (4H, d, J=8.3 Hz, CArH), 8.22 (2H, s, CH=N).

Example 2. Bis[2-(tosylamide)benzyliden-N-octadecylamino]zinc (R=C18H37)

Analogously to example 1 get out of 0.53 g of 2-(N-tosylamide)benzal octadecylamine white crystals with TPL230-231°C. the Yield of 0.48 (89%). Found, %: C 68.92; H 8.73, N 5.17, Zn 5.97. For C64H98N4O4S2Zn calculated, %: C 68.82, H 8.54, N 5.02, Zn 5.85.

1H NMR spectrum, CDCl3, δ, ppm: 0.88 (6N, t, J=of 6.71 Hz, CH2CH3), 1.02-1.26 (N, m, CH2), 3.32-3.36 (2H, m, CH2), 4.35-4.37 (2H, m, CH2), 6.8 (2H, t, J=7.4 HZ, CArH), 7.05 (4H, d, J=8.1 Hz, CArH), 7.17-7.23 (4H, m, CArH), 7.49 (2H, d, J=8.5 Hz, CArH), 8.04 (4H, d, J=8.3 Hz, CArH), 8.2 (2H, s, CH=N).

The obtained compounds were investigated by standard methods, spectral-absorption and spectral-luminescent properties in a solution of acetonitrile at T=293 K.

Compounds Ia, where R1=R2=C18H37and Ib, where R1=R2=C7H15have the following meanings:

- absorption characteristics: the maximum of the absorption band λ (Ia)=274 and 353 nm, λ (Ib)=270 and 350 nm; molar extinction coefficients at the maximum of the absorption band ε (Ib)=20800 and 11500 l·mol-1·cm-1;

- characteristics of fluorescence: the band maximum fluorescence λ (Ia)=428 nm, λ (Ib)=428 nm (blue region); the band maximum fluorescence excitation λ (Ia)=350 nm, λ (Ib)=347 nm; quantum yield of fluorescence φ (Ia)=0,37, φ (Ib)=0,23.

1. Bis[2-(tosylamide)benzyliden-N-alkylamine]zinc General formula
,
where Ts=tosyl, R=C7-C18alkyl.

2. Bis[2-(tosylamide)benzyliden-K-alkilinity]zinc according to claim 1, where R=C7H15.

3. Bis[2-(tosylamide)benzyliden-N-alkylamine]zinc according to claim 1, where R=C18H37.



 

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