CN102320991A - New molecule of PH fluorescent probe - Google Patents
New molecule of PH fluorescent probe Download PDFInfo
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- CN102320991A CN102320991A CN201110235335A CN201110235335A CN102320991A CN 102320991 A CN102320991 A CN 102320991A CN 201110235335 A CN201110235335 A CN 201110235335A CN 201110235335 A CN201110235335 A CN 201110235335A CN 102320991 A CN102320991 A CN 102320991A
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- fluorescent probe
- dinaphthylamine
- new molecule
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Abstract
The invention, belonging to the field of chemistry, relates to a new compound, a new molecule of a PH fluorescent probe, characterized in that: a light pink acicular crystal synthesized by 1,8-dinaphthylamine and salicylaldehyde is used, the chemical name of the crystal is N,N'-bis(salicylaldehyde semicarbazone)-1,8-dinaphthylamine. Compared with the prior art, the new molecule has narrow PH response range, high sensitivity, and no background interference, and is suitable for the PH detection in strong acid environment. According to the invention, the application range is wide, especially the application in the life field is broadened, or has important value in precise determination of PH of cell sap in the fields of sports medicine and sports biochemistry.
Description
Technical field
The invention belongs to chemical field, relate to a kind of new compound, specifically is a kind of PH fluorescent probe recruit.
Background technology
The method of existing mensuration pH value, the most frequently used is the electrochemical method of PH glass electrode.Because glass electrode has certain limitation; As receive the electricity interference; Receive the interference of metals ion, factors such as the destruction of pair cell and acid error existence, exist pH value less than 1 or occur during greater than 9 mensuration than mistake be not suitable for defective such as life field pH value mensuration.
Measure the existing report of fluorescent probe of pH value, be applied to industry, environment and medical field.Compare with electrochemical method, though can eliminate background interference preferably, sensitivity is improved a lot; But be applied in the life field, since its sensing range broad still, many reached at 6-8 PH unit; The physiology PH that can only be applied to pH value 6-8 usually detects, for a lot of strong acidic environments, like the detection of hydrochloric acid in gastric juice, ribozyme, lysosome etc.; Exist and disturbed by metals ion, sensitivity can not meet the demands, the defective that can not be suitable for.
Summary of the invention
The contriver be engaged in for many years chemistry and with the teaching in chemical relevant field, scientific research activity in; Find existing P H pH-value determination pH technology, especially the PH fluorescent probe exists certain defective, through continuous exploratory development; Also do not see at present relevant PH fluorescent probe recruit's of the present invention report; Purpose is to provide a kind of PH fluorescent probe recruit, can realize that the PH responding range is narrower, and sensitivity is higher; Enlarge and detect Application Areas, more accurately be suitable for the PH fluorescent probe of the strong acid environment that detects the life field.
The technical scheme that the present invention takes is to propose a kind of PH fluorescent probe recruit, and its chemical name is: N, N '-two (salicylidene is amino)-1,8-dinaphthylamine; Its structural formula is:
；
Its form is the lightpink needle-like crystal, about 180 ℃ of fusing points; Nuclear-magnetism H spectrum: 1H NMR (DMSO-d6) (1 ppm): 9.724 (s, 2H ， – CH=N); 6.521 – 7.491 (m Ar – H); 5.669 (s, 2H ,-OH).
PH fluorescent probe recruit of the present invention adopts 1, and 8-dinaphthylamine and salicylic aldehyde compound method are prepared from.During preparation,, the lightpink post precipitation occurs and continue to stir above-mentioned two kinds of raw material mixing solutionss reflux in water-bath; Cooling; With the solid product recrystallization that generates, the lightpink needle-like crystal product that obtains at last is the alleged PH fluorescent probe recruit of the present invention.
Synthetic route is following:
This PH fluorescent probe recruit of the present invention compares with existing P H fluorescent probe, because can be in narrower PH scope (1.99-3.49; Have only 1.5 PH units); Response Table reveals very high sensitivity, does not receive the interference of backgrounds such as metals ion, is applicable to remarkable advantages such as strong acid environment; Will the broadened application field; Particularly will play the application of more widening, accurately measure at the pH value of body fluid such as field pair cell liquid such as sports medical science and sports biochemistry, athletic physiology and have certain important value, will bring into play significant role in fields such as life in the life field.
Description of drawings
Fig. 1 representes a kind of PH fluorescent probe of the present invention recruit's nuclear magnetic spectrogram;
Fig. 2 representes a kind of PH fluorescent probe of the present invention recruit's infrared spectrogram;
Fig. 3 representes that the present invention is used to measure the fluorescence spectrum figure of the solution of different PH.
Embodiment
In conjunction with accompanying drawing and embodiment, further specify a kind of PH fluorescent probe of the present invention recruit's preparation method and measuring method.
During preparation, salicylic aldehyde (2-8mmol) ethanolic soln is added to saturated 1, in 8-dinaphthylamine (1-5mmol) ethanolic soln; With this mixing solutions reflux in 40-80 ℃ water-bath, begin to occur the deposition of lightpink behind the 5-30min, continue stirring reaction 10-50min; Reduce to room temperature, obtain the solid product of lightpink, use ethyl alcohol recrystallization; Obtain the needle-like crystal-N of lightpink, N '-two (salicylidene is amino)-1,8-dinaphthylamine; Be that preparation cost is invented a kind of PH fluorescent probe recruit, its nuclear magnetic spectrogram is seen Fig. 1, and its infrared spectrogram is seen Fig. 2.
Fluorescence experiments: PH fluorescent probe recruit's of the present invention aqueous ethanolic solution (solvent: ethanol/water=1/9); Fluorescence spectrum intensity with the solution of the different pH values of fluorescent spectrophotometer measuring; Excitation wavelength: 330nm sees Fig. 3, and converses the environment PH of surveying by the relation of fluorescence intensity and pH value.Show that PH responding range of the present invention can have only 1.5 PH units 1.99-3.49, sensitive tolerance range is very high.
Claims (1)
1. PH fluorescent probe recruit, its chemical name is N, N '-two (salicylidene is amino)-1, the 8-dinaphthylamine, structural formula is
, its form is the lightpink needle-like crystal, about 180 ℃ of fusing points, nuclear-magnetism H spectrum: 1H NMR (DMSO-d6) (1 ppm): 9.724 (s, 2H ， – CH=N); 6.521 – 7.491 (m Ar – H); 5.669 (s, 2H ,-OH).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN 201110235335 CN102320991B (en) | 2011-08-17 | 2011-08-17 | New molecule of PH fluorescent probe |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110235335 CN102320991B (en) | 2011-08-17 | 2011-08-17 | New molecule of PH fluorescent probe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102320991A true CN102320991A (en) | 2012-01-18 |
| CN102320991B CN102320991B (en) | 2013-07-17 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 201110235335 Expired - Fee Related CN102320991B (en) | 2011-08-17 | 2011-08-17 | New molecule of PH fluorescent probe |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592987A (en) * | 2014-12-30 | 2015-05-06 | 深圳先进技术研究院 | Restoring-type near infrared fluorescence probe with pH response and preparation method and application thereof |
| CN107478632A (en) * | 2017-09-22 | 2017-12-15 | 南昌航空大学 | A kind of method of fluoroscopic examination pH value by pH test paper |
| CN113912612A (en) * | 2021-08-24 | 2022-01-11 | 南京林业大学 | Alkaline pH fluorescent probe pyridazino [4,5-b ] quinoxaline-1, 4-diamine Schiff base and preparation method and application thereof |
-
2011
- 2011-08-17 CN CN 201110235335 patent/CN102320991B/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| DAVER M. BOGHAEI ET AL.: "Non-symmetrical tetradentate vanadyl Schiff base complexes derived from 1,2-phenylene diamine and 1,3-naphthalene diamine as catalysts for the oxidation of cyclohexene", 《TETRAHEDRON》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592987A (en) * | 2014-12-30 | 2015-05-06 | 深圳先进技术研究院 | Restoring-type near infrared fluorescence probe with pH response and preparation method and application thereof |
| CN107478632A (en) * | 2017-09-22 | 2017-12-15 | 南昌航空大学 | A kind of method of fluoroscopic examination pH value by pH test paper |
| CN107478632B (en) * | 2017-09-22 | 2019-12-24 | 南昌航空大学 | Method for detecting pH value through fluorescence of pH test paper |
| CN113912612A (en) * | 2021-08-24 | 2022-01-11 | 南京林业大学 | Alkaline pH fluorescent probe pyridazino [4,5-b ] quinoxaline-1, 4-diamine Schiff base and preparation method and application thereof |
| CN113912612B (en) * | 2021-08-24 | 2022-08-05 | 南京林业大学 | Alkaline pH fluorescent probe pyridazino [4,5-b ] quinoxaline-1, 4-diamine Schiff base and preparation method and application thereof |
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| Publication number | Publication date |
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| CN102320991B (en) | 2013-07-17 |
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