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Multi-ion difference detection fluorescent probe taking carbazole Schiff base as recognition receptor

A carbazole, to-be-detected technology, applied in the field of multi-ion differential fluorescent probes, can solve problems such as few probes, and achieve the effects of good anti-interference ability, mild reaction conditions and simple operation

Active Publication Date: 2020-09-08
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, there are still few probes for the differential detection of multimetal ions
Multiple-ion detection systems are of great value and can simultaneously detect more than one ion of interest in the presence of interfering ions. The development of selective fluorescent probes for the simultaneous detection of multiple metal ions has drawn attention from biology and the environment. There is great interest in the field, but challenges remain in obtaining simple, reliable, green, economically cost-effective, highly selective multi-ion differential recognition of metal ions

Method used

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  • Multi-ion difference detection fluorescent probe taking carbazole Schiff base as recognition receptor
  • Multi-ion difference detection fluorescent probe taking carbazole Schiff base as recognition receptor
  • Multi-ion difference detection fluorescent probe taking carbazole Schiff base as recognition receptor

Examples

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Embodiment 1

[0033] Example 1 Synthesis of 3-formyl-9-benzylcarbazole-(S)-methyl ester dithiocarbonylhydrazone (L1)

[0034] Add 10.0mmol 3-formyl-9-benzylcarbazole, 12.0mmol methyl hydrazinodithiocarbamate and 1.2mmol) p-toluenesulfonic acid in a dry glass mortar, grind at room temperature, TLC monitoring ( Developing agent V (DCM / PE)=2:1) ​​until the reaction is complete. The mixture was washed with water until neutral, filtered and dried to obtain a crude product. The crude product was recrystallized from absolute ethanol to obtain the pure product, that is, 3-formyl-9-benzylcarbazole-(S)-methyl ester dithiocarbonylhydrazone (L1), light yellow solid, yield 92.3% , m.p.: 162.6-164.1℃.

[0035] FT-IR (KBr) ν: 3286 (ν = C-H ), 2979, 2911 (ν C-H ),1688(ν C＝N ), 1586, 1523, 1461 (ν C＝C ),1312(δ C-H ),1213(ν C-N ).

[0036] 1 H NMR (400MHz, DMSO) δ: 13.30(s, 1H, -NH), 8.48(s, 1H, HC=N), 8.42-7.16(m, 12H, Ar-H), 5.71(s, 2H, N -CH 2 ),2.54(s,3H,S-CH 3 ).

[0037] 13 C NMR(101MHz,...

Embodiment 2

[0038] Example 2 Synthesis of 3-formyl-9-n-propylcarbazole-(S)-benzyl ester dithiocarbonylhydrazone (L2) Add 10.0mmol 3-formyl-9- n-Propylcarbazole, 12.0mmol benzyl hydrazinodithiocarbamate and 2.1g (12.0mmol) p-toluenesulfonic acid were ground at room temperature and monitored by TLC (developing agent V(DCM / PE)=2:1 ) until the reaction is complete. The mixture was washed with water until neutral, filtered and dried to obtain a crude product. The crude product was recrystallized from absolute ethanol to obtain the pure product, that is, 3-formyl-9-n-propylcarbazole-(S)-benzyl dithiocarbonylhydrazone (L2), light yellow solid, yield 92.5 %, m.p.:181.9-184.6℃.

[0039] FT-IR(KBr)ν:3116(ν ＝C-H ), 2956, 2865 (ν C-H ), 1591 (ν C＝N ),1512(ν C＝C ),1318(δ C-H ),1227(ν C-N ).

[0040] 1 H NMR (400MHz, CDCl 3 )δ: 8.35(s, 1H, HC=N), 8.13-7.34(m, 12H, Ar-H), 4.61(s, 2H, S-CH 2 ),4.30-4.26(m,2H,N-CH 2 ),1.94-1.91(m,2H,-CH 2 ),0.95-0.98(m,3H,-CH 3 ).

[0041] 13 C NMR (100MH...

Embodiment 3

[0042] Example 3 Synthesis of 3-formyl-9-n-butylcarbazole-(S)-benzyl ester dithiocarbonylhydrazone (L3) Add 10.0mmol 3-formyl-9- n-Butylcarbazole, 12.0mmol benzyl hydrazinodithiocarbamate and 2.1g (12.0mmol) p-toluenesulfonic acid were ground at room temperature and monitored by TLC (developing agent V(DCM / PE)=2:1 ) until the reaction is complete. The mixture was washed with water until neutral, filtered and dried to obtain a crude product. The crude product was recrystallized from absolute ethanol to obtain the pure product, that is, 3-formyl-9-n-butylcarbazole-(S)-benzyl dithiocarbonylhydrazone (L3) was obtained as light yellow flaky crystals, producing The rate is 93.6%, m.p.155.5-158.3℃.

[0043] FT-IR(KBr)ν:3107(ν N-H ), 2958, 2858 (ν C-H ),1608(ν C＝N ), 1527, 1453 (ν C＝C ),1371(δ C-H ),1241(ν C-N ).

[0044] 1 H NMR (400MHz, CDCl 3 )δ: 8.35(s, 1H, HC=N), 8.13-7.30(m, 12H, Ar-H), 4.60(s, 2H, S-CH 2 ),4.32-4.29(m,2H,N-CH 2 ),1.87-1.83(m,2H,-CH 2 ),1.41-1.46(m...

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Abstract

The invention provides a synthesis method of a multi-ion difference detection fluorescent probe taking carbazole Schiff base as a recognition receptor. The synthesis method comprises the following steps: adding A mol of 3-formyl-9-alkylcarbazole, B mol of hydrazinodithioformate and C mol of p-toluenesulfonic acid into a dry glass mortar, grinding at room temperature, carrying out TLC monitoring until the reaction is complete, washing the mixture with water until the mixture is neutral, filtering and drying to obtain a crude product, and recrystallizing the crude product with absolute ethyl alcohol to obtain a pure product, namely the carbazolyl-containing Schiff base fluorescent probe. The method is simple to operate, efficient, economical, environment-friendly and low in cost. The probe can achieve the following technical effects that Fe<3+> and Cu<2+> ions can be recognized with high selectivity, multi-ion differential response to Fe<3+> and Cu<2+> ions can be realized, rapid detection of Cu<2+> and Fe<3+> ions can be realized, and the anti-interference capability is good.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a multi-ion differential fluorescent probe using carbazole Schiff base as a recognition receptor. Background technique [0002] The demand for metal ion recognition in health and environmental applications has been very high in recent years. The specific detection of metal ions is of great significance in chemistry, biology and environmental technology. Iron is a key trace element in living organisms, mainly Fe 2+ (ferrous) and Fe 3+ Existing in the form of iron (iron), they enter the body through the body mainly through red meat, cereals, fish, beans, leafy vegetables, etc., and play an important role in it. In the bio-inorganic field, i.e. it transports various gas molecules (oxygen, carbon dioxide), transfers electrons and constructs enzymes (catalase, lipoxygenase), iron deficiency can lead to serious health problems, mainly anemia. Also, during preg...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06G01N21/6428C09K2211/1029G01N2021/6432G01N2021/6443
Inventor 尹大伟刘玉婷党阳
Owner SHAANXI UNIV OF SCI & TECH