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Dibromo monomer and preparation method thereof, water-soluble random copolymer and preparation method thereof, and fluorescent sensor
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A technology for water-soluble, dibromo compounds, applied in the field of chemical analysis and detection, can solve the problems of inconspicuous detection signals and few types, and achieve the effect of high selectivity and excellent water-solubility
Active Publication Date: 2021-07-23
WUHAN INSTITUTE OF TECHNOLOGY
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Problems solved by technology
At present, there are few types of fluorescent probes used for iron ion detection, and the detection signal is not obvious. Few can detect iron ions in aqueous media.
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Embodiment 1
[0039] The preparation method of the dibromo compound (A) containing 4,5-diazafluorene unit:
[0040]
[0041] Add 120 parts (molar parts) of 2,5-dibromoaniline and 100 parts (molar parts) of 4,5-diazofluoren-9-one into a three-neck round bottom flask, add an appropriate amount of glacial acetic acid, and stir thoroughly . In pass N 2 Under certain conditions, the temperature was raised to 120° C., and the reaction was carried out for 6 hours. After being cooled to room temperature, filtered, washed with water, washed with methanol, and purified by recrystallization to obtain compound (A), IR (KBr, cm -1 ): 3081, 3042, 3009, 1658, 1574, 1514, 1397, 1279, 1076, 1029, 872, 800, 752.
Embodiment 2
[0043] Preparation of water-soluble random conjugated polymers:
[0044]
[0045] Add 10 parts (mmol) of dibromomonomer (A) containing 4,5-diazofluorene structure, 10 parts (mmol) of 1,4-dibromo-2 , 5-bis(3-propoxy sodiumsulfonate) benzene (B), 21 parts (mmol) terephthalic diboronic acid (C), appropriate amount of Na 2 CO 3 solution (1M) and catalyst Pd (Phh 3 ) 4 , 200 parts (g) of double-distilled N,N-dimethylformamide, reacted at 155°C for 72 hours, added excess methanol after cooling, collected the precipitate by suction filtration, and dissolved the filter cake with a small amount of water / methanol, Add a large amount of acetone to separate out the solid, suction filter, and repeat the above steps three times for the gained solid to obtain a water-soluble random conjugated polymer, IR (KBr, cm -1): 2977, 1658, 1443, 1409, 1193, 1049, 904, 866, 675.
Embodiment 3
[0047] Implementation process of water-soluble random conjugated polymer fluorescent sensor for metalion recognition performance:
[0048] Prepare the fluorescent chemical sensor standard detection solution and use it as a fluorescent sensor: accurately weigh 7.291mg of the compound with a precision balance, add it to a 10ml volumetric flask, and dilute to 10ml with deionized water. Draw 1ml into another 100ml volumetric flask bell, dilute to 100ml with absolute ethanol, and prepare a concentration of 1×10 -5 mol / L standard detection solution;
[0049] Prepare different metalion solutions: Accurately weigh the following metal salts (AgNO 3 ,BaCl 2 2H 2 O,CaCl 2 ,Cd(NO 3 ) 2 4H 2 O,CoCl 2 ·6H 2 O,FeCl 2 4H 2 O,FeCl 3 ·6H 2 O,HgCl 2 , KCl, LiCl, MgCl 2 ·6H 2 O,MnCl 2 4H 2 O,NaCl,NiCl 2 ·6H 2 O,SrCl 2 ·6H 2 O,ZnCl 2 ) each 1mmol, dissolved in 10ml of deionized water, prepared to a concentration of 1 × 10 -1 mol / L metal ion solution. Dilute to 1×10 accor...
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Abstract
The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a dibromo monomer containing 4,5-diazafluorene, a preparation method thereof, a water-soluble random copolymer, a preparation method thereof, and a fluorescence sensor. The preparation method of the water-soluble random copolymer comprises the following steps: 1) under argon protection, dibromo compounds containing 4,5-diazafluorene groups, 1,4-dibromo-2,5- Two (3-propoxysodium sulfonate) benzene and terephthalic diboronic acid join in the organic solvent in molar ratio; 2) add catalyst again, heating reaction, after cooling, add excess methyl alcohol to dissolve, then filter and obtain solid phase, to The solid phase is purified to obtain the water-soluble random conjugated polymer. The water-soluble random conjugated polymer provided by the present invention has excellent water solubility; make Fe with it 3+ Fluorescent chemical sensors are highly selective. Highly selective recognition of Fe by fluorescencequenching phenomenon 3+ , not interfered by common metal ions.
Description
technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a dibromomonomer containing 4,5-diazafluorene, a preparation method thereof, a water-soluble random copolymer, a preparation method thereof, and a fluorescence sensor. Background technique [0002] Iron ions are widely distributed in nature and are one of the important transition metals in many biological systems and chemicals. However, after water or food is contaminated by iron ions, if the content is too high after drinking or eating into the human body, it will cause great damage to the heart, liver, and pancreas, and will also cause mental decline. Life is in danger. Moreover, the iron element ingested by the human body mainly comes from drinking water and food. Generally, the iron element in drinking water is easier to be absorbed by people than the iron element in food. Therefore, it is very important to realize the rapid and sensitive ...
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