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4,5-disubstituted-1,8-naphthoyl imide compounds and use thereof

A technology of naphthalene imide and compound, which is applied in the field of highly selective photosensitive identification and ratio detection, and achieves the effects of easy availability of raw materials, high derivatization and simple synthesis

Inactive Publication Date: 2006-12-06
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there are no reports of ratiometric fluorescent probes for copper ions

Method used

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  • 4,5-disubstituted-1,8-naphthoyl imide compounds and use thereof
  • 4,5-disubstituted-1,8-naphthoyl imide compounds and use thereof
  • 4,5-disubstituted-1,8-naphthoyl imide compounds and use thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027]Add 0.1g (0.31mmol) 4-bromo-5-nitro-1,8-naphthalene anhydride in a 25ml flask, add 10ml ethanol and heat to reflux, cool to 50°C after a while, slowly add 0.0227g butane Amine (0.31mmol) in 5ml ethanol solution, the originally cloudy solution suddenly became clear, and the color also deepened, turning red. Heating continued to reflux, and the TLC plate followed the reaction after 40 min. After distillation of ethanol under reduced pressure, silica gel column separation, CHCl 3 elute. Recrystallized from ethanol to finally obtain the product as white needle-like crystals, weighing 47 mg, with a yield of 40.2%. The melting point is 175.8-176.2°C. 1 H-NMR (CDCl 3 , 400MHz) 60.99(t, J=7.2Hz, 3H), 1.45(m, J=7.2Hz, 2H), 1.71(m, J=7.2Hz, 2H), 4.18(t, J=7.2Hz, 2H) , 7.93(d, J=8.0Hz, 1H), 8.21(d, J=8.0Hz, 1H), 8.51(d, J=8.0Hz, 1H), 8.71(d, J=8.0Hz, 1H). 13 C-NMR (CDCl 3 , 100MHz), 613.95, 20.49, 30.21, 40.92, 122.69, 123.72, 124.26, 125.99, 131.37, 132.49, 136....

Embodiment 2

[0029]

[0030] In a 25ml flask, add 100mg (0.266mmol) N-butyl 4-bromo-5-nitro-1,8-naphthalimide, add 10ml ethylene glycol monomethyl ether to dissolve, add N-phenyl - Ethylenediamine 0.15ml (1.05mmol), heating. After 4min the reaction was over. Poured into water, extracted with dichloromethane, and purified by chromatographic column to obtain a yellow solid with a yield of 87%. The melting point is 186.2-187.5°C. 1 H-NMR (CDCl 3 , 400MHz): 60.946-0.983(t, J=7.6Hz, 3H), 1.401-1.458(m, J=7.6Hz, 2H), 1.654-1.711(m, J=7.6Hz, 2H), 3.640(br, 4H), 4.111-4.149(t, J=7.6Hz, 2H), 6.714-6.834(br, 4H), 7.221-7.262(t, J=8Hz, 3H), 7.752-7.771(d, J=7.6Hz, 1H), 7.826 (s, N-H), 8,264-8.284 (d, J=8Hz, 1H), 8.425-8.446 (d, J=8Hz, 1H).

Embodiment 3

[0032]

[0033] Dissolve more than 120mg of the product in 10ml of ethylene glycol monomethyl ether, then add 1ml of N-phenylethylenediamine, and reflux until the reaction is complete. It was poured into water, extracted with dichloromethane, and purified by chromatographic column to obtain a yellow solid weighing 136 mg with a yield of 74%. The melting point is 203.5-204.1°C. 1 H-NMR (CDCl 3 , 400MHz) δ0.936-0.972(t, J=7.2Hz, 3H), 1.395-1.450(m, J=7.2Hz, 2H), 1.669-1.704(m, J=7.2Hz, 2H), 3.351-3.425 (dd, J=5.2Hz, 4H) 4.104-4.140(t, J=7.2Hz, 2H), 6.195(s, N-H), 6.538-6.559(d, J=8.4Hz, 1H), 6.672-6.692(d , J=8.4Hz, 4H), 6.766-6.803(t, J=7.6Hz, 2H), 7.191-7.230(d, J=7.6Hz, 4H), 8.265-8.286(d, J=8.4Hz, 2H) . 13 C-NMR (CDCl 3 , 400MHz): δ14.060, 20.671, 30.608, 40.028, 43.474, 44.036, 107.252, 113.590, 119.010, 129.797, 132.26, 133.615, 147.893, 152.205, 164.661. HRMS(EI)calcd for C 32 h 35 N 5 o 2 [M] 521.2791, found 521.2779.

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Abstract

The invention provides 4,5-disubstituted-1,8-naphthoyl imines fluorescent compound with same or different 4,5-position aromatic amine( heterocyclic aromatic amine) substituent as acceptor and naphthoyl imine as chromophore matrix. In organic solvent, 4,5-position is replaced separately by aromatic amine or heterocyclic aromatic amine to produce symmetrical or asymmetric compound with 4-bromo-5-nitro-1,8-anhydride naphthalene as raw materials. The fluorescent compound is used as rate fluorescent probe which can detect the copper ion in buffer solution and has high sensitivity and high selectivity.

Description

technical field [0001] The present invention relates to a class of 4,5-aryl (or heterocyclic) amino disubstituted-1,8 naphthimide compounds and their synthesis and use as ratiometric fluorescent probes for highly selective photosensitive recognition and recognition of copper ions in buffer solutions. Ratio detection. Background technique [0002] Due to the importance of copper ions in chemistry, environment, medicine and life sciences, the research on fluorescent probes for copper ions has attracted extensive attention in recent years. (Y Zheng, et al, J.Am.Chem.Soc.2003, 125, 2680-2686) But so far, almost all reported copper ion fluorescent probes use the enhancement or weakening of fluorescence as optical signals. Response to copper ions is achieved. And because copper ions are well-known strong fluorescence quenchers, only a few fluorescent probes can increase fluorescence when recognizing copper ions. (S.Kaur, S.Kumar, Chem.Commun.2002, 2840-2841; S.Banthia, A.Samant...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/06C07D401/04C07D405/04C07D409/04G01N21/64
Inventor 钱旭红崔京南徐兆超肖义
Owner DALIAN UNIV OF TECH
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