Phenothiazinyl quinazoline fluorescence ion probe and application thereof

A phenothiazinyl quinazoline, fluorescent ion technology, applied in the field of fluorescent ion probes, can solve problems such as hindering probe sensitivity, and achieve the effects of high sensitivity and high selectivity

Inactive Publication Date: 2012-09-12
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This greatly hinders the improvement of probe sensitivity, and it is urgent to develop new varieties

Method used

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  • Phenothiazinyl quinazoline fluorescence ion probe and application thereof
  • Phenothiazinyl quinazoline fluorescence ion probe and application thereof
  • Phenothiazinyl quinazoline fluorescence ion probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1, the preparation of compound ECQP:

[0023] Weigh 2.85 g (14.6 mmol) 9-ethylcarbazole in a three-necked flask, N 2 Add 16 mL DMF and 20 mL 1,2-dichloroethane under protection, and add 16 mL (175 mmol, ρ=1.675) POCl dropwise from the constant pressure funnel under stirring 3 , the dropwise addition was completed, the temperature was raised to 80 °C for 8 h, cooled, the reaction solution was poured into water, neutralized with dilute ammonia water to weak acidity, extracted with dichloromethane, purified by silica gel chromatography, and recrystallized from ethanol to obtain 9-ethyl- 2.82 g of 3-formyl-9H-carbazole is a pale yellow solid. Yield: 86.6%. m.p.: 84-85 o c. 1 H NMR (CDCl 3 , 400MHz) δ (ppm): 1.43-1.47 (t, 3H), 4.34-4.40 (m, 2H), 7.31-7.34 (t, 1H), 7.43-7.46 (d, 2H), 8.52-7.56 (t, 1H), 7.98-8.08 (d, 1H), 8.13-8.15 (d, 1H), 8.58 (s, 1H), 10.08 (s, 1H). GC MS (m / z): 223 (M + ).

[0024] Weigh 1.56 g (7 mmol) 9-ethyl-3-formyl-9H-carbazole, 0.95...

Embodiment 2

[0028] Embodiment 2, ECQP ultraviolet absorption spectroscopic titration experiment:

[0029] Compound ECQP was formulated as 2 × 10 -5 mol / L dichloromethane solution, pipette 2.5 mL of the prepared compound ECQP solution in a fluorescence cuvette, and drop 5 μL 1×10 -3 mol / L of Cu 2+ solution in acetonitrile until equilibrium is reached (ie, the absorption spectrum no longer changes appreciably). Without adding Cu 2+ , there were three absorption peaks in the absorption spectrum of ECQP, among which the absorption peak at 245 nm belonged to the characteristic absorption of quinazoline, while the absorption around 300 nm and 344 nm belonged to the characteristic absorption of carbazole and phenothiazine, respectively. When adding 0~1 eq Cu 2+ A new absorption peak appeared at 410 nm, and with Cu 2+ The addition of increased gradually, indicating that the addition of Cu 2+ Formed a complex with ECQP (as shown in the accompanying drawing figure 1 shown). When continui...

Embodiment 3

[0030] Embodiment 3, ECQP fluorescence spectrum titration experiment:

[0031] Compound ECQP was formulated as 2 × 10 -5 mol / L dichloromethane solution, pipette 2.5 mL of the prepared compound ECQP solution in a fluorescence cuvette, and drop 5 μL 1×10 -3 mol / L of Cu 2+ solution in acetonitrile until equilibrium is reached (i.e., the spectrum no longer changes appreciably). Without adding Cu 2+ , ECQP does not emit light in dichloromethane solution, with Cu 2+ (0~3 eq) of acetonitrile solution, an emission peak appeared at 504 nm, and with Cu 2+ The addition gradually increased. It can be observed that adding 0~1 eq Cu 2+ When , the emission peak intensity increases slowly, while adding 1~3 eq Cu 2+ When , the intensity increases rapidly, and reaches the maximum at 3 eq (as shown in the accompanying drawing image 3 shown).

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Abstract

The invention relates to a phenothiazinyl quinazoline fluorescence ion probe and application thereof. A fluorescence chemical sensor is based on a phenothiazinyl-substituted quinazoline derivative, and the structural general formula of the derivative is shown as a formula (1), wherein R1 is a hydrogen atom, alkyl which contains 1 to 10 carbon atoms, ether, azyl, aliphatic amide, imide, an ester group, an aryl substituent group or a hybrid aryl substituent group. Compared with other macromolecule fluorescence probe molecules, the fluorescence ion probe has the characteristics of simplicity in dissolution and synthesis and the like, and good response and identification effects on Cu<2+>, and also has a good identification effect on Hg<2+> in the presence of Cu<2+>, and generates different fluorescence responses to Hg<2+> and Cu<2+> under different conditions, multifunctionality on ion detection, and can also be designed into ion light introducing or fluorescence inhibit (INH) logic gate.

Description

technical field [0001] The invention belongs to the technical field of fluorescent ion probes, and in particular relates to a class of phenothiazinylquinazoline fluorescent ion probes and their application in metal ion detection. The research on fluorescent ion switches and logic gates is also of great importance. role. Background technique [0002] Metal ions participate in many processes of life activities, and can complex with many biomolecules to participate in the metabolic process of life, which plays a very important role in maintaining normal life activities. e.g. Cu 2+ , lack of Cu in the human body 2+ Hematopoietic function will be affected and anemia will also be caused. In the human body, many biochemical reactions are catalyzed by enzymes. There are at least 11 kinds of oxidases in the human body, all of which contain Cu 2+ . In recent years, the research results of scientists have shown that the copper element in the human body plays a very important role ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D417/14G01N21/64
Inventor 梅群波王玲霞黄维童碧海翁洁娜张彬蒋渊知
Owner NANJING UNIV OF POSTS & TELECOMM
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