CN105486668B - Fast-response Hg based on rhodamine B-thiophene derivant2+The preparation method of chromogenic-fluorogenic probe - Google Patents
Fast-response Hg based on rhodamine B-thiophene derivant2+The preparation method of chromogenic-fluorogenic probe Download PDFInfo
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Abstract
The present invention relates to a kind of fast-response Hg based on rhodamine B thiophene derivant2+The preparation method of color fluorescent probe.Condensation acylation reaction is carried out by rhodamine B and diethylenetriamine; obtain rhodamine B diethylenetriamine derivative; rhodamine B diethylenetriamine derivative and 2 thiophenecarboxaldehydes are subjected to condensation reaction again; a kind of rhodamine B thiophene derivant is obtained, the water-ethanol mixed solution based on rhodamine B thiophene derivant is somebody's turn to do and can be used as fast-response Hg2+Color fluorescent probe.The present invention can be used for Hg in quick analysis water-like2+The fast-response color fluorescent probe of content, it is to other metal ions（Na+, K+, Mg2+, Fe3+, Cu2+, Zn2+, Cr3+）Strong antijamming capability, applicable pH range is acid to neutrality, is a kind of ideal Hg2+Color fluorescent probe；The Hg2+Colored indicator is to Hg2+Response time be less than 2 minutes, lowest detection is limited to 2.0 × 10‑7mol/L；The present invention has many advantages, such as that simple synthesis technology, of low cost, easy to operate, high sensitivity, fast response time, detection limit is low, application prospect is extensive.
Description
Technical field
The present invention relates to a kind of mercury ions（Hg2+）Detection agent, and in particular to a kind of based on rhodamine B-thiophene derivant
Fast-response Hg2+The preparation method of chromogenic-fluorogenic probe.
Background technology
In global industry process, human activity causes the heavy metal ion content in environment increasingly to increase, pollution
Range is also growing.China's heavy metal pollution of water body problem is very prominent, and the pollution rate of river,lake and reservior substrate is up to 80.1%
[such as Zhou Huaidong, Peng Wenqi water environments and the Beijing aquatic ecological restoration：Chemical Industry Press, 2005].Early in the eighties
Find that have in many water bodys such as Jinsha jiang River, Xiang River, Ji canal, Communities of The Jinzhou Bay different degrees of heavy metal-polluted in first investigation
Dye, wherein the water phase heavy metal concentration in serious location is up to hundreds of ppb, Heavy Metal In Sediments concentration reaches thousands of ppm [Ho K
C, Hui K C C. Chemical contamination of the East River (Dongjiang) and its
implication on sustainable development in the Pearl River Delta. Environment
International, 2001, 26 (5, 6): 303-308].The Yellow River, Huaihe River, Song Hua River, Liaohe River in 2003 etc. ten are flowed greatly
The pollution level of the basin piece heavy metals exceeding standard section in domain is to surpass V class [ten large watershed piece Water Pollution Problem of the China Hu Bibin
And main feature environmental sciences, 2003,25: 15-17].On January 15th, 2012, Guangxi Longjiang power stations He Lalang net cage
It breeds fish and a small amount of dead fish phenomenon occurs, further investigation reveals that, 200 meters of 80 times of water quality heavy metals exceeding standards before unrestrained harbour are drawn in Longjiang river Yizhou.
The Spring Festival in lunar calendar Year of the Dragon, Longjiang section detect that heavy metal Hg content is exceeded so that littoral and downstream DRINKING WATER safety is by tight
It threatens again.The cause of this event, which is the illegal blowdown of Liang Ge producers, causes mercury leakage rate to reach about 20 tons.
Mercury is a kind of very harmful environmental contaminants, in recent years China《Heavy metal pollution integrated control is planned》With《" ten
Two or five " atmosphere pollution groupcontrol in key area is planned》The pollution of mercury and its integrated control are all included in major fields.In planning
It explicitly points out：During " 12th Five-Year Plan ", the computation model of typical coal unit emission inventories is established, carries out coal-burning power plant's Mercury In The Air
Discharge on-line monitoring pilot work；Develop pilot project early as possible, while flue gas ash removal, desulphurization and denitration, control mercury is dirty
Dye realizes jointly controlling for multi-pollutant, and carries out net assessment to the economy, technology and environmental benefit of project.Environmental protection
Portion also proposed the instruction for promoting atmosphere pollution groupcontrol, reinforces clean energy and utilizes, stringent control pollution that caused by coal burning
The multi-pollutants Collaborative Control technologies such as fired power generating unit flue gas ash removal, desulphurization and denitration and the removal of mercury are developed in discharge, increase emphasis pollution
Object prevents dynamics.
It is seriously affected caused by mercury pollution, promotes the continuous research and development of mercury ion detecting technology.It is common right
The method that mercury ion is detected has Atomic absorption/emission spectrometry, atomic fluorescence method, inductively coupled plasma method, X-ray
Fluorescent spectrometry, Inductively coupled plasma-mass spectrometry, inductively coupled plasma atomic emission spectrometry, immunoassay, electricity
Chemical method, biochemical sensor method etc..These methods are although each advantageous, but there are still prodigious disadvantages in actual use
End, such as sensitivity is low, expensive equipment and complicated for operation, these methods need special laboratory, profession operating technology
Personnel and complicated sample pretreatment process, expend and take, it is desirable that and it is too high, moreover to certain heavy metal ion and insensitive, very
The problems such as can not extremely detecting, is not suitable for the detection to water sample, soil and food equal samples in daily life, can not meet and answer
Needs when to accident.In burst mode tra nsmitter investigation and the ecological risk investigation of basin regional scale, due to
Regional extent is wide, needs the environmental sample quantity acquired big, and there is an urgent need to high throughput, real-time field screening technologies.Therefore,
It is great to seek a kind of simple, quick, sensitive heavy metal ion qualitative and quantitative detection technical meaning.
Secondly, the type of mercury ion is more, content is low, sample composition is complicated, has mobility and unstability, according to environment
The characteristics of middle mercury ion, determines that the analytical technology of mercury ion and method need sensitive, accurate, real-time, fast analysis.In order to
It cuts down the number of intermediate links, measures the content and pollution level of mercury ion in the environment, quantitative detection is carried out to pollutant in real time.Mesh
The developing direction of preceding environment measuring in the world is：Online, in real time, easy, portable, high sensitivity, detection limit is low, sensitivity is good,
The measurement that can be used for complex sample can be used for the environmental sample of separate sources for large batch of detection.
In addition, because of mercury ion long-term existence, simultaneously chronic pollution natural environment, can also be produced in the case of extremely micro
Raw adverse consequences, how scientifically the pollution level of evaluation environment mercury ion, how to prevent and remedy pollution etc. all be unable to do without to mercury ion
Content analysis, therefore carry out micro-/trace amount mercury ion analysis have very important significance.
In recent years, the chromogenic-fluorogenic of the color and change in fluorescence mechanism detection metal ion that are generated based on ion induction is visited
Needle technology is low, easy to operate, at low cost due to having the characteristics that high sensitivity, detection limit, has become detection mercury ion at present
Important means [Mao J, He Q, Liu W S. An " off-on " the fluorescence probe for of pollution
chromium(III) ion determination in aqueous solution. Anal Bioanal Chemistry,
2010, 396: 1197-1203；Dong M, Wang Y W, Peng Y. Highly selective ratiometric
fluorescent sensing for Hg2+ and Au3+ respectively in aqueous media. Organic
Letters, 2010, 12:5310-5313], people are designing each metal ion species chromogenic-fluorogenic using Molecular Recognition Principle
Greatly success is achieved in terms of probe technique and is widely used in the fields such as chemistry, biology and environmental science.Rhodamine
（Rhodamine）Due to its outstanding spectral quality, such as long wave effect weakening, higher fluorescent quantum conversion ratio and strong mole
Extinction coefficient [Haugland R P. A guide to fluorescent probes and labeling
Technologies. Invitrogen Corporation, Karlsbad, CA, 2005], therefore, it has become a kind of wide
The general chromogenic-fluorogenic probe used.In recent years, it was reacted with primaquine using the carboxyl in rhodamine structure and generates unique five yuan
Cyclic lactam structures, by combining heavy metal ion, make originally without color, the lactam structure molecule of not no fluorescent effect
Open loop is converted into the amide structure for having very strong absorbability in visible-range and sending out very hyperfluorescence, and reaching detection, certain is heavy
The report of metal ion is increasing.Due to having the characteristics that Response Mechanism is unique, detection is sensitive, interference is few, it is based on rhodamine
The chromogenic-fluorogenic probe of class molecule is widely applied in the detection of heavy metal and transition metal ions, detectable heavy
Metal ion includes Cu2+, Pb2+, Zn2+, Hg2+Deng.
The signal route of rhodamine B given below and heavy metal ion effect.It is shown below, the Luo Dan of closed loop configuration
Bright molecule molar absorption coefficient and fluorescence quantum yield are all very low, almost without fluorescence.But after connecting recognition group R,
It can have an effect with certain heavy metal species or transition metal ions under the synergistic effect of carbonyl and recognition group, so as to cause probe
Lactam bond is broken, and forms open loop structure, the fluorescence intensity of molecule is caused to significantly increase, and is realized and is known to the sensitivity of the ion
Not.
The cyclization and ring opening process of rhodamine B lactam structure
But the chromogenic-fluorogenic probe for studying more mercury ion at present mostly uses the original of organic group complexation of metal ions
Reason, thus chromogenic-fluorogenic probe is mostly the molecule containing organic heterocyclic, solubility is not satisfactory in aqueous solution.In addition, micro-/trace
The combination effect for measuring mercury ion and chromogenic-fluorogenic probe is still not ideal enough, therefore detection sensitivity and the scope of application are by perhaps
More limitations find sensitiveer, efficient detection agent and are still problem of the pendulum in face of us for mercury ion.
Invention content
It is an object of the invention to overcome the shortcomings of the prior art, propose a kind of based on rhodamine B-thiophene derivant
Fast-response Hg2+Chromogenic-fluorogenic probe preparation method.
A kind of fast-response Hg based on rhodamine B-thiophene derivant proposed by the present invention2+Chromogenic-fluorogenic probe, it is first
Condensation acylation reaction is first carried out by rhodamine B and diethylenetriamine, obtains rhodamine B diethylenetriamine derivative；The rhodamine B
With thiophenecarboxaldehyde acyl chloride reaction occurs for diethylenetriamine derivative again, obtains a kind of rhodamine B-thiophene derivant；The rhodamine
The water-ethanol mixed solution of B- thiophene derivants can be used as Hg2+Color fluorescent probe, in the rhodamine B-thiophene derivant
Hg2+Hg is added in the water-ethanol mixed solution of chromogenic-fluorogenic probe2+Afterwards, the color of mixed solution becomes pink from colourless,
Absorption peak in corresponding uv-visible absorption spectroscopy at 560 nm is with Hg2+The raising of concentration and enhance；The rhodamine B-
The fast-response Hg of thiophene derivant2+Chromogenic-fluorogenic probe is to Hg2+Response time be less than 2 minutes, lowest detection is limited to
2.0×10-7Mol/L, and can be used for micro- in water environment/trace Hg2+Half-quantitative detection.
A kind of fast-response Hg based on rhodamine B-thiophene derivant proposed by the present invention2+Chromogenic-fluorogenic probe
The synthetic route of preparation method, the rhodamine B-thiophene derivant is as follows：
It is as follows：
（1）It weighs 1 ~ 10 g rhodamine Bs and 20 ~ 200 mL alcoholic solvents is added in 250 mL reaction bulbs, being sufficiently stirred makes
Rhodamine B is completely dissolved, and 1 ~ 10 mL diethylenetriamines are added dropwise in the case where being kept stirring, under nitrogen protection in 75 ~
Reaction bulb, is cooled to room temperature, filters and rotate removing solvent, gained Light brown solid by 85 DEG C of 4 ~ 40 h of reaction after reaction
It is extracted 2 ~ 4 times with 40 ~ 400 mL dichloromethane, merges organic phase, be washed with water 3 ~ 5 times, dried 2 ~ 20 hours with anhydrous sodium sulfate,
Filtering collects filtrate, crocus solid is rotated to obtain, after column chromatography for separation（Solvent is methanol：Dichloromethane=1：5, v/v）,
Obtain rhodamine B-diethylenetriamine derivative, yield 85%-95%.
（2）Weigh rhodamine B-diethylenetriamine derivative and the anhydrous second of 10 ~ 100 mL made from 0.5 ~ 5 g steps (1)
Alcohol is added in 250 mL reaction vessels, and being sufficiently stirred makes to be completely dissolved, then 0.5 ~ 5 g 2 thiophene carboxaldehydes are dissolved in 2 ~ 20
In mL absolute ethyl alcohols, it is added dropwise in 250 mL reaction vessels using constant pressure funnel, under nitrogen protection in 60~90 DEG C
4 ~ 24 h are reacted, rotate out absolute ethyl alcohol after reaction, are extracted 2 ~ 4 times with 10 ~ 100 ml dichloromethane, organic phase is merged,
It is washed with water 2 ~ 4 times, obtains organic phase, dried 1 ~ 10 hour with anhydrous sodium sulfate, dichloromethane is rotated out, after column chromatography for separation
（Solvent is methanol：Dichloromethane=1：10, v/v）Obtain light yellow solid, as rhodamine B-thiophene derivant, yield 80%-
95%。
（3）Rhodamine B-the thiophene derivant for weighing the preparation of 0.01 ~ 0.1 g steps (3) is dissolved in 100 ~ 1000 g water and alcohol
A kind of fast-response Hg based on rhodamine B-thiophene derivant is obtained in the mixed solution of solvent composition2+Chromogenic-fluorogenic is visited
Needle.
In the present invention, the chemical structural formula of rhodamine B is as follows：
In the present invention, the chemical structural formula of diethylenetriamine is as follows：
In the present invention, the chemical structural formula of 2 thiophene carboxaldehyde is as follows：
In the present invention, alcoholic solvent described in step (1) and (3) uses any, step in ethyl alcohol, methanol or isopropanol
(3) volume ratio of water described in and alcoholic solvent is 1：10~10：1, which has good solubility,
Reach 0.01 ~ 1 mmol/L, can be used as a kind of fast-response Hg based on rhodamine B-thiophene derivant2+Chromogenic-fluorogenic is visited
Needle.
It is an advantage of the invention that：1. the present invention is a kind of fast-response Hg based on rhodamine B-thiophene derivant2+It is aobvious
The preparation method of color-fluorescence probe can be used for Hg in quick analysis water-like2+The fast-response chromogenic-fluorogenic probe of content, it
To other coexistent metallic ions in water sample（Na+, Fe3+, Pb2+, Zn2+, Mg2+, Fe2+, Cr3+）Strong antijamming capability,
Applicable pH range is wide（Acidity arrives neutrality）, it is a kind of efficient mercury ion color fluorescent probe；2. rhodamine B-thiophene should be based on
The fast-response Hg of derivative2+Chromogenic-fluorogenic probe is to Hg2+Response time be less than 2 minutes, lowest detection is limited to 2.0 ×
10-7mol/L；3. the present invention has simple synthesis technology, of low cost, easy to operate, high sensitivity, fast response time, detection
The advantages that low, application prospect is extensive is limited, can be used for the real-time and quick measurement of complex sample in water environment, it can also be used to micro-/trace
Measure the half-quantitative detection of ion concentration of mercury.
Description of the drawings
Fig. 1 is the chemical structural formula of rhodamine B-thiophene derivant（a）And its and Hg2+Combination principle schematic diagram（b）.
Fig. 2 is the nuclear-magnetism hydrogen collection of illustrative plates of rhodamine B-thiophene derivant.
Fig. 3 is the fast-response Hg based on rhodamine B-thiophene derivant2+A different huge sum of moneys are being added in chromogenic-fluorogenic probe
Belong to the color change situation after ion（From left to right：Na+, K+, Mg2+, Fe3+, Cu2+, Zn2+, Cr3+, Hg2+）.
Fig. 4 is the fast-response Hg based on rhodamine B-thiophene derivant2+Hg is being added in chromogenic-fluorogenic probe2+Afterwards not
With the uv-visible absorption spectrum figure of time（Solvent：Water-ethanol, 3:1, v/v）.
Fig. 5 is the fast-response Hg based on rhodamine B-thiophene derivant2+Various concentration is added in chromogenic-fluorogenic probe
Hg2+Uv-visible absorption spectrum figure afterwards（Solvent：Water-ethanol, 3:1, v/v）.
Fig. 6 is the fast-response Hg based on rhodamine B-thiophene derivant2+Different metal is being added in chromogenic-fluorogenic probe
Ion（Hg2+,Na+, Fe3+, Pb2+, Zn2+, Mg2+, Fe2+, Cr3+Deng）Fluorescence spectrum spectrogram afterwards.
Specific implementation mode
Said program is described further below in conjunction with specific embodiment.It should be understood that these embodiments are for illustrating
The present invention and be not limited to limit the scope of the invention.The implementation condition used in embodiment can be done according to the condition of specific producer
Further adjustment, the implementation condition being not specified is usually the condition in routine experiment.
With reference to embodiment, the present invention will be described in detail, it should be understood that citing described herein is only used to explain this
Invention, is not intended to limit the present invention.
Embodiment 1
It weighs 3 g rhodamine Bs and 60 mL ethyl alcohol is added in 250 mL there-necked flasks, being sufficiently stirred keeps rhodamine B completely molten
Solution, is added dropwise 3.00 mL diethylenetriamines dropwise, 80 DEG C of back flow reactions is added dropwise 10 hours, and reaction process lead to nitrogen, and reaction is tied
Reaction bulb is cooled to room temperature after beam, is filtered, revolving removes ethyl alcohol, and gained Light brown solid extracts 3 with 100 mL dichloromethane
It is secondary, merge organic phase, be washed with water 4 times, is dried 2 hours with anhydrous sodium sulfate, filtering collects filtrate, rotates to obtain crocus solid,
After column chromatography for separation（Solvent is methanol：Dichloromethane=1：5, v/v）, rhodamine B-diethylenetriamine derivative is obtained, is produced
Rate is 93.2%.
It weighs the above-mentioned rhodamine Bs of 2.0 g-diethylenetriamine derivative and 50 mL absolute ethyl alcohols is added to 250 mL reactions
In container, being sufficiently stirred makes to be completely dissolved, then 0.5 g 2 thiophene carboxaldehydes are dissolved in 10 mL absolute ethyl alcohols, uses constant pressure
Dropping funel is added dropwise in 250 mL reaction vessels, reacts 6 h in 80 DEG C under nitrogen protection, rotates out nothing after reaction
Water-ethanol is extracted 3 times with 30 ml dichloromethane, is merged organic phase, is washed with water 3 times, obtains organic phase, dry with anhydrous sodium sulfate
Dry 5 hours, dichloromethane is rotated out, after column chromatography for separation（Solvent is methanol：Dichloromethane=1：10, v/v）It obtains light yellow
Solid, as rhodamine B-thiophene derivant, yield 84%.
Above-mentioned rhodamine B-the thiophene derivants of 0.01 g are weighed, the mixed solution of 500 g water and ethyl alcohol is dissolved in（Water：Ethyl alcohol
= 5：1, volume ratio）In, obtain a kind of fast-response Hg based on rhodamine B-thiophene derivant2+Chromogenic-fluorogenic probe.
The chemical structural formula of the rhodamine B-thiophene derivant is as shown in Figure 1, Fig. 2 is the core of rhodamine B-thiophene derivant
Magnetic hydrogen collection of illustrative plates, Fig. 3 are the fast-response Hg based on rhodamine B-thiophene derivant2+Chromogenic-fluorogenic probe is different heavy in addition
Color change situation after metal ion（From left to right：Na+, K+, Mg2+, Fe3+, Cu2+, Zn2+, Cr3+, Hg2+）, Fig. 4 is to be based on
The fast-response Hg of rhodamine B-thiophene derivant2+Hg is being added in chromogenic-fluorogenic probe2+The ultraviolet-visible of different time afterwards
Light absorption spectrogram（Solvent：Water-ethanol, 3:1, v/v）, Fig. 5 is the fast-response Hg based on rhodamine B-thiophene derivant2+It is aobvious
Various concentration Hg is added in color-fluorescence probe2+Uv-visible absorption spectrum figure afterwards（Solvent：Water-ethanol, 3:1, v/v）, Fig. 6
It is the fast-response Hg based on rhodamine B-thiophene derivant2+Different metal ions are being added in chromogenic-fluorogenic probe（Na+, K+, Mg2+, Fe3+, Cu2+, Zn2+, Cr3+, Hg2+）Fluorescence spectrum spectrogram afterwards.
Embodiment 2：It is same as Example 1, but the volume ratio of water and ethyl alcohol becomes 4 in step (3): 1.
Embodiment 3：It is same as Example 1, but the volume ratio of water and ethyl alcohol becomes 6 in step (3): 1.
Embodiment 4：It is same as Example 1, but the volume ratio of water and ethyl alcohol becomes 3 in step (3): 1.
Embodiment 5：It is same as Example 1, but the volume ratio of water and ethyl alcohol becomes 2 in step (3): 1.
Embodiment 6：It is same as Example 1, but the volume ratio of water and ethyl alcohol becomes 1 in step (3): 1.
Embodiment 7：It is same as Example 1, but ethyl alcohol becomes methanol in step (3), other are constant.
Embodiment 8：It is same as Example 1, but ethyl alcohol becomes isopropanol in step (3), other are constant.
Rhodamine B-the thiophene derivant and Hg obtained in embodiment 2-82+There are special combinations, and with it is other often
See metal ion（Na+, K+, Mg2+, Fe3+, Cu2+, Zn2+, Cr3+）Do not have this effect then.Derive in the rhodamine B-thiophene
Hg is added in the water-ethanol mixed solution of object2+Afterwards, solution colour becomes red from colourless, in uv-visible absorption spectroscopy
There is absorption peak in correspondence at 560 nm, shows that it is a kind of efficient Hg2+Chromogenic-fluorogenic probe.It should be based on rhodamine B-thiophene
The Hg of derivative2+Chromogenic-fluorogenic probe is limited to 2.0 × 10 to the lowest detection of ion concentration of mercury-7 Mol/L, applicable pH range are
Acidity arrives neutrality.The Hg based on rhodamine B-thiophene derivant2+The probe chromogenic-fluorogenic response time is less than 2 minutes, ultraviolet-
The intensity and fluorescence intensity of visible absorption characteristic peak are with Hg2+The raising of concentration and enhance, still conform to line at low concentrations
Sexual intercourse can be used for the half-quantitative detection of micro-/trace amount mercury ion concentration.
The foregoing examples are merely illustrative of the technical concept and features of the invention, its object is to allow the person skilled in the art to be
It cans understand the content of the present invention and implement it accordingly, it is not intended to limit the scope of the present invention.It is all smart according to the present invention
The equivalent transformation or modification that refreshing essence is done, should be covered by the protection scope of the present invention.
Claims (3)
1. a kind of fast-response Hg based on rhodamine B-thiophene derivant2+The preparation method of chromogenic-fluorogenic probe, feature
It is to be as follows：
（1）It weighs 1 ~ 10 g rhodamine Bs and 20 ~ 200 mL alcoholic solvents is added in 250 mL reaction bulbs, being sufficiently stirred makes Luo Dan
Bright B is completely dissolved, and 1 ~ 10 mL diethylenetriamines is added dropwise in the case where being kept stirring, under nitrogen protection in 75 ~ 85 DEG C
4 ~ 40 h are reacted, are after reaction cooled to room temperature reaction bulb, filter and rotate removing solvent, gained Light brown solid is with 40
~ 400 mL dichloromethane extract 2 ~ 4 times, merge organic phase, are washed with water 3 ~ 5 times, are dried 2 ~ 20 hours with anhydrous sodium sulfate, mistake
Filter collects filtrate, rotates to obtain crocus solid, and after column chromatography for separation, solvent is the volume ratio 1 of methanol and dichloromethane：
5, obtain rhodamine B-diethylenetriamine derivative, yield 85%-95%；
（2）Rhodamine B-diethylenetriamine derivative and 10 ~ 100 mL absolute ethyl alcohols made from 0.5 ~ 5 g steps (1) are weighed to add
Enter into 250 mL reaction vessels, being sufficiently stirred makes to be completely dissolved, then by 0.5 ~ 5 g 2 thiophene carboxaldehydes be dissolved in 2 ~ 20 mL without
It in water-ethanol, is added dropwise in 250 mL reaction vessels using constant pressure funnel, reacts 4 in 60~90 DEG C under nitrogen protection
~ 24 h, rotate out absolute ethyl alcohol after reaction, are extracted 2 ~ 4 times with 10 ~ 100 ml dichloromethane, merge organic phase, then use water
It washes 2 ~ 4 times, obtains organic phase, dried 1 ~ 10 hour with anhydrous sodium sulfate, rotate out dichloromethane, after column chromatography for separation, expansion
Agent is the volume ratio 1 of methanol and dichloromethane：10, light yellow solid is obtained, as rhodamine B-thiophene derivant, yield 80%-
95%；
（3）Rhodamine B-the thiophene derivant for weighing the preparation of 0.01 ~ 0.1 g steps (2) is dissolved in 100 ~ 1000 g water and alcoholic solvent
A kind of fast-response Hg based on rhodamine B-thiophene derivant is obtained in the mixed solution of composition2+Chromogenic-fluorogenic probe.
2. a kind of fast-response Hg based on rhodamine B-thiophene derivant according to claim 12+Chromogenic-fluorogenic is visited
The preparation method of needle, it is characterised in that alcoholic solvent described in step (1) and (3) is any in ethyl alcohol, methanol or isopropanol, step
Suddenly the volume ratio of water and alcoholic solvent described in (3) is 1：10~10：1, which forms in water and alcoholic solvent
Mixed solution in solubility be 0.01 ~ 1 mmol/L.
3. a kind of fast-response Hg based on rhodamine B-thiophene derivant according to claim 12+Chromogenic-fluorogenic is visited
The preparation method of needle, it is characterised in that the chemical structural formula of rhodamine B-thiophene derivant is as follows：
。
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| CN108516979B (en) * | 2018-05-18 | 2020-08-25 | 华东理工大学 | Compound based on naphthalimide-rhodamine and application thereof |
| CN108395889A (en) * | 2018-05-25 | 2018-08-14 | 泰山医学院 | Mercury ion fluorescence probe and its application of benzimidazole [1,2-a] and pyridine derivatives |
| CN108997363B (en) * | 2018-07-20 | 2020-12-25 | 山西大学 | Derivative based on rhodamine B and preparation method and application thereof |
| CN109824683B (en) * | 2019-04-01 | 2022-02-11 | 南京林业大学 | Rhodamine B Hg based on 2-thiopheneacetyl chloride2+Preparation and application of fluorescent sensor |
| CN112708015B (en) * | 2020-12-28 | 2023-01-13 | 齐鲁工业大学 | Rhodamine 6G derivative-based fluorescence sensor and preparation method thereof |
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