A carbazole schiff base as a fluorescent probe for multi-ion differential detection of receptors

A carbazole, to-be-detected technology, applied in the field of multi-ion differential fluorescent probes, can solve the problem of few probes, achieve good anti-interference ability, high yield, and simple operation

Active Publication Date: 2022-01-25
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • A carbazole schiff base as a fluorescent probe for multi-ion differential detection of receptors
  • A carbazole schiff base as a fluorescent probe for multi-ion differential detection of receptors
  • A carbazole schiff base as a fluorescent probe for multi-ion differential detection of receptors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of 3-formyl-9-benzylcarbazole-(S)-methyl ester dithiocarbonylhydrazone (L1)

[0035] 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℃.

[0036] 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) .

[0037] 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 ).

[0038] 13 C NMR(101MHz,DMSO)δ:197.02(s,2H)...

Embodiment 2

[0039] 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℃.

[0040] 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 ).

[0041] 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 ).

[0042] 13 C NMR (100MHz, CDCl...

Embodiment 3

[0043] 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℃.

[0044] 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 ).

[0045] 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,2H,-C...

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Abstract

The invention provides a method for synthesizing a fluorescent probe for multi-ion differential detection using carbazole Schiff base as a recognition acceptor. Add A mol 3-formyl-9-alkylcarbazole, B mol hydrazinodithioformate and C mol p-toluenesulfonic acid in a dry glass mortar, grind at room temperature, TLC monitoring to The response is complete. The mixture was washed with water until neutral, filtered and dried to obtain a crude product. The crude product was recrystallized from anhydrous ethanol to obtain the pure product, that is, a fluorescent probe containing a carbazole-based Schiff base was obtained. The invention has the advantages of simple operation, high efficiency, economy, greenness, environmental protection and low cost. This type of probe can achieve the following technical effects: Highly selective recognition of Fe 3+ and Cu 2+ Ion; can be on Fe 3+ and Cu 2+ ions to achieve multi-ion differential response; can achieve Cu 2+ and Fe 3+ Rapid detection of ions; and good anti-interference ability.

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