CN108865113A - For detecting Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-and preparation method - Google Patents

For detecting Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-and preparation method Download PDF

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CN108865113A
CN108865113A CN201710990072.9A CN201710990072A CN108865113A CN 108865113 A CN108865113 A CN 108865113A CN 201710990072 A CN201710990072 A CN 201710990072A CN 108865113 A CN108865113 A CN 108865113A
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pyrroles
naphthaldehyde
boron fluorine
hydroxyl
bis
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CN108865113B (en
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陈玉婷
张英
张秀玲
张瑜
姚艺伟
黄莎莎
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Dezhou University
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    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N2021/6432—Quenching

Abstract

The present invention relates to the preparation technical fields of organic compound, and disclosing one kind can be used for detecting Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde -, preparation process is to utilize the double pyrroles's boron fluorine compounds of 8- (3- hydroxyl -4- nitrobenzene methyl) and NH2NH2‑H2O prepares presoma 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorine compounds；Then it is produced using 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorine compounds and 2- hydroxyl -1- naphthaldehyde and obtains the aforementioned bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde -.The bis- pyrroles's boron fluorine fluorescent molecular probes of the naphthaldehyde-are in detection Fe3+With Co2+In use, it has many advantages, such as that selectivity is good, identity and high sensitivity, and then there is important application value and wide application prospect；In its preparation process, reaction condition is mild, and yield is high, is not required in preparation process by special installation, implementation easy to spread.

Description

For detecting Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-and preparation Method
Technical field
The invention belongs to organic compound preparation technical fields, and in particular to one kind can be used for detecting Fe3+、Co2+Fluorescence Molecular probe and preparation method.
Background technique
With the development of society, problem of environmental pollution has become China or even world and sustainable economic development institute face One of main problem faced.For example, the metal ions such as lead, cadmium, mercury have wide application in current industrial production, but work as They with cationic form with industrial wastewater or soot emissions to nature after, serious dirt is caused to atmosphere and entire water system Dye, brings significant damage to the ecosystem and environment for human survival.In addition, in many life processes cation also play it is important Effect, for example, iron is one of required microelement in animal body, body hematopoiesis, in terms of with not Alternative effect, however, can all lead to that immunity of organisms is low, nervous function when intracellular iron concentration is too high or too low The various diseases such as disorder.Therefore, develop efficient, convenient and fast ion detection method to life science, chemical and environment section Etc. is all of great significance.
In many analyzing detecting methods, high sensitivity, good, the easy-operating fluorescent molecular probe of selectivity are had become as people One of the focus studied.Fluorescent molecular probe is on the basis of both molecular recognition and fluorescent technique organically combine, by glimmering Optical signal group and target recipient are formed by connecting by specific mode.Currently, demand of the people according to measurement target, by right The modification of optical signalling group and design by volume primitive are based on photo induced electron transfer, Intramolecular electron transfer, fluorescence resonance energy The signals transformation mechanism such as amount transfer, has synthesized the fluorescent molecular probe of Numerous, Various Functions.But prepared at present The fluorescence probe overwhelming majority only has recognition performance, the fluorescence based on multiple substrate recognition performance point to single ionic (or molecule) Sub- probe research is less, and in actual chemistry or biosystem, a variety of anions and canons and neutral small molecule exist simultaneously, Often not only one species be we pay close attention to and detection target (substrate).Therefore, design preparation has Multiple detection performance Fluorescent molecular probe has important theory significance and application prospect.
Double pyrroles's boron fluorine fluorophor are to fix rigidly to be conjugated made of two pyrrole rings by boron bridged bond and methine bridged bond to put down Face structure has good photostability, higher molar absorption coefficient and fluorescence quantum yield, adjustable excitation and transmitted wave Length, molecular structure is easy to the advantages that modifying, and is one of most common fluorescence signal group.People pass through to double pyrroles's boron fluorine The conjugation regulation and substitution modification of different loci around fluorogen, on its periphery, introducing is various gives electron-accepting group and identifies base Group has synthesized fluorescence probe [N.Boens, the V.Leen and that series has different recognition performances and possible optical transitions mechanism W.Dehaen,Chem.Soc.Rev.,2012,41,1130-1172].But it is that double pyrroles's boron fluorine fluorogens are constructed, can simultaneously it is right Fe3+、Co2+Fluorescent molecular probe with detection performance is not reported also.
Summary of the invention
Technical purpose of the invention is to provide a kind of couple of Fe3+、Co2+With the bis- pyrroles's boron of naphthaldehyde-for stablizing recognition performance Fluorine fluorescent molecular probe.
It is a kind of with the double pyrroles's boron fluorinations of 8- (3- hydroxyl -4- nitrobenzene methyl) another technical object of the present invention is to provide Conjunction object and 2- hydroxyl -1- naphthaldehyde are as reaction raw materials, the method for preparing the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde -.
To realize the above-mentioned technical purpose, the present invention adopts the following technical scheme that：
One kind is for detecting Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-, structural formula is：
One kind is for detecting Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-preparation method comprising such as Lower step：
1) preparation of 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorine compounds
In the reaction vessel, by the double pyrroles's boron fluorine compounds of α mmol 8- (3- hydroxyl -4- nitrobenzene methyl) using in right amount Methanol is dissolved, and β mL NH is sequentially added2NH2-H2O (80%), γ mg Pd/C, under nitrogen protection, heating, stirring condition Sufficiently reaction through cooling, filters, is evaporated acquisition solid matter, and solid matter is carried out silica gel chromatograph separation, with methylene chloride/ Methanol (49:1) make solvent, obtain 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorinated compounds, it is crystalline in aubergine； Wherein α:β:γ is 5:7:100；
2) preparation of the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-
By the double pyrroles's boron fluorine compounds of δ mmol 8- (3- hydroxyl -4- aminobenzene methyl) and ε mmol 2- hydroxyl -1- naphthaldehyde It is put into reaction vessel, is dissolved with appropriate dehydrated alcohol, ζ mL glacial acetic acid is added, wherein δ:ε:ζ is 2:2:1；It is protected in nitrogen Under shield, reaction mixture is warming up to 75 degree, reacts 3~8 hours, obtains red suspension, the cooling, mistake by the red suspension Filter, dehydrated alcohol washing, vacuum drying, obtain the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-, take on a red color powdered, structure Formula is：
The synthetic route chart of the preparation method of the above-mentioned bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-is：
The present invention has the advantages that：
(1) in the preparation process of the bis- pyrroles's boron fluorine fluorescent molecular probes of this naphthaldehyde -, with 8- (3- hydroxyl -4- aminobenzoic Base) double pyrroles's boron fluorine compounds and 2- hydroxyl -1- naphthaldehyde be raw material, ethyl alcohol is solvent, and reaction temperature is 75 degree, reaction condition temperature With, yield is high, and it is easily operated, it is practical, it is not required in preparation process by special installation, it is easy to implement；
(2) in the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-prepared by the present invention, double pyrroles's boron fluorine fluorescence signal groups By C=N group and hydroxyl naphthalene aldehyde bridging, the transmitting of fluorescent molecular probe signal had not only been increased, but also has enhanced fluorescent molecule spy For the complex performance of detection ion；
(3) pass through ultraviolet absorption spectroscopy and fluorescence emission spectrometry analysis detection this naphthaldehyde-bis- pyrroles boron fluorine fluorescence point Sub- probe finds it to Fe the selectivity of different metal ions3+With Co2+It is special that different dual signal responses is shown respectively Property；As detection Fe3+With Co2+Fluorescent molecular probe use, have many advantages, such as that selectivity is good, identity and high sensitivity, And then there is important application value and wide application prospect.
Detailed description of the invention
The nucleus magnetic hydrogen spectrum figure of compound obtained by Fig. 1 embodiment 1-3.
The mass spectrogram of compound obtained by Fig. 2 embodiment 1-3.
The UV absorption light after different metal ions is added in Fig. 3 naphthaldehyde-bis- pyrroles boron fluorine fluorescent molecular probe in DMF Spectrum.
The fluorescence emission after different metal ions is added in Fig. 4 naphthaldehyde-bis- pyrroles boron fluorine fluorescent molecular probe in DMF Spectrum.
Specific embodiment
It is disclosed by the invention to be used to detect Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-, structural formula is：
Above-mentioned is used to detect Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probe preparation process of naphthaldehyde-be, it is sharp first With the double pyrroles's boron fluorine compounds of 8- (3- hydroxyl -4- nitrobenzene methyl) and NH2NH2-H2O prepares presoma 8- (3- hydroxyl -4- ammonia Base benzyl) double pyrroles's boron fluorine compounds；Then 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorine compounds and 2- are utilized Hydroxyl -1- naphthaldehyde prepares the bis- pyrroles's boron fluorine fluorescent molecular probes of aforementioned naphthaldehyde-as reaction raw materials；The conjunction of whole preparation process It is at route map：
Embodiment 1
1) the double pyrroles's boron fluorine compounds preparations of 8- (3- hydroxyl -4- aminobenzene methyl)
In the 50mL three neck round bottom flask equipped with return pipe, nitrogen protection device, it is put into 8- (the 3- hydroxyl-of 0.5mmol 4- nitrobenzene methyl) double pyrroles's boron fluorine compounds, are dissolved with 25mL methanol, sequentially add the NH of 0.7mL2NH2-H2O (80%), The Pd/C of 10mg；Be warming up to reflux under nitrogen atmosphere, magnetic agitation stops after reacting 6 hours, through cooling, filter, be evaporated it is molten Agent obtains the solid matter in dark red, is separated to the solid matter with silica gel chromatograph, with methylene chloride/methanol (49:1) make exhibition Agent is opened, obtains two azole compounds 131mg of 8- (3- hydroxyl -4- aminobenzene methyl) boron fluorine, yield 74% is crystalline in aubergine；
2) preparation of compound A
Under the conditions of nitrogen protection, by 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorine compounds of 0.2mmol and 2- hydroxyl -1- the naphthaldehyde of 0.2mmol be put into equipped with return pipe, nitrogen protection device 50mL three neck round bottom flask in, use 15mL Dehydrated alcohol is dissolved, and the glacial acetic acid of 0.1mL is added；Then reaction mixture is brought rapidly up under magnetic stirring to 75 Degree reacts 3 hours, and the obtained suspended reaction solution of red is cooled to room temperature, and is successively filtered, dehydrated alcohol washing, vacuum It is dry, compound A 58mg is obtained, yield 57% takes on a red color powdered.
Embodiment 2
1) the double pyrroles's boron fluorine compounds preparations of 8- (3- hydroxyl -4- aminobenzene methyl), it is identical as 1 preparation method of embodiment；
2) preparation of compound B
Under the conditions of nitrogen protection, by 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorine compounds of 0.2mmol and 2- hydroxyl -1- the naphthaldehyde of 0.2mmol be put into equipped with return pipe, nitrogen protection device 50mL three neck round bottom flask in, use 15mL Dehydrated alcohol is dissolved, and 0.1mL glacial acetic acid is added；Then reaction mixture is brought rapidly up under magnetic stirring to 75 Degree reacts 6 hours, and the obtained suspended reaction solution of red is cooled to room temperature, and is successively filtered, dehydrated alcohol washing, vacuum It is dry, compound B 59mg is obtained, yield 58% takes on a red color powdered.
Embodiment 3
1) the double pyrroles's boron fluorine compounds preparations of 8- (3- hydroxyl -4- aminobenzene methyl), it is identical as 1 preparation method of embodiment；
2) preparation of compound C
Under the conditions of nitrogen protection, by 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorine compounds of 0.2mmol and 2- hydroxyl -1- the naphthaldehyde of 0.2mmol be put into equipped with return pipe, nitrogen protection device 50mL three neck round bottom flask in, use 15mL Dehydrated alcohol is dissolved, and the glacial acetic acid of 0.1mL is added；Then reaction mixture is brought rapidly up under magnetic stirring to 75 Degree reacts 8 hours, and the obtained suspended reaction solution of red is cooled to room temperature, and is successively filtered, dehydrated alcohol washing, vacuum It is dry, compound C 58mg is obtained, yield 57% takes on a red color powdered.
Compound A, compound B and the compound C obtained respectively to embodiment 1-3 carries out analysis measurement, the nuclear-magnetism of three Hydrogen spectrogram is consistent, and data are as follows：?1H NMR(CDCl3, 400MHz) in, it include 1-N=CH proton signal peak:δ15.77 (d,1H)；1 phenyl ring-OH proton signal peak：10.73 (s, 1H), 1 naphthalene nucleus-OH proton signal peak：9.52 (d, 1H), 11 Aromatic rings proton signal peak：8.37(d,1H),8.07(s,1H),7.75(d,1H),7.61(d,1H),7.38(t,1H),7.21 (t,1H),7.13(d,1H),6.99(d,1H),6.75(d,1H),6.13(s,2H)；6 CH3Proton signal peak：2.44(s, 3H),1.51(s,3H).Three's mass spectrogram is consistent, and it is 509.06 that compound, which surveys quasi-molecular ions (m/e),.It can confirm compound A, change Close object B and compound C molecular structure be：
That is the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-.
Embodiment 4
Detection of the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-to different metal ions selectivity.
In the bis- pyrroles's boron fluorine fluorescent molecular probe DMF solutions of naphthaldehyde-that concentration is 10 μM, it is separately added into 10 times of moles Different metal ions, by ultra-violet absorption spectrum variation find, be added Na+、K+、Mg2+、Ba2+、Ca2+、Mn2+、Cd2+、Ni2+、 Hg2+、Cu2+、Zn2+After equal metal ions, maximum absorption band is not changed significantly at the position 502nm；Fe is added3+Afterwards, naphthalene Absorption peak slightly red shift of the bis- pyrroles's boron fluorine fluorescent molecular probes of aldehyde-at 502nm is simultaneously slightly reduced along with absorbance, simultaneously There are two strong absworption peaks at 310nm and 360nm in it；Co is added2+Afterwards, the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-exist It is absorbed between 300nm-500nm without relatively strong；These statistics indicate that, the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-are to Fe3+、Co2+ There is ion different UV absorption spectroscopys to respond, and have certain detection potential to them.
Embodiment 5
The detection that the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-respond different metal ions fluorescence spectroscopy.
In the DMF solution of the bis- pyrroles's boron fluorine fluorescent molecules of naphthaldehyde-, be separately added into the different metals of 10 times of moles from Son can be found by the variation of fluorescence emission spectrum, and Na is added+、K+、Mg2+、Ba2+、Ca2+、Mn2+、Cd2+、Ni2+、Hg2+、Cu2+、 Zn2+After equal metal ions, the bis- pyrroles's boron fluorine fluorescent molecules of naphthaldehyde-the position 515nm maximum fluorescence emission spectrum almost without Variation；And Fe is added3+Afterwards, lead to the slightly red shift of fluorescence emission peak of the fluorescent molecular probe at 515nm, and intensity obviously increases By force；As addition Co2+Afterwards, the maximum fluorescence emission of fluorescent molecular probe probe is almost quenched completely；It is indicated above that this naphthaldehyde- Double pyrroles's boron fluorine fluorescent molecular probes are to Fe3+、Co2+Ion is respectively provided with significant and different fluorescent emission spectroscopy response, to this Two metal ion species have specific fluorescence analysis detection performance.

Claims (2)

1. one kind is for detecting Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-, structural formula is：
2. one kind is for detecting Fe3+、Co2+The bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-preparation method comprising following step Suddenly：
1) preparation of 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorine compounds
In the reaction vessel, α mmol 8- (3- hydroxyl -4- nitrobenzene methyl) double pyrroles's boron fluorine compounds are utilized into proper amount of methanol It is dissolved, sequentially adds β mL NH2NH2-H2O (80%), γ mg Pd/C, under nitrogen protection, heating, stirring condition sufficiently Reaction through cooling, filters, is evaporated acquisition solid matter, solid matter is carried out silica gel chromatograph separation, with methylene chloride/methanol (49:1) make solvent, obtain 8- (3- hydroxyl -4- aminobenzene methyl) double pyrroles's boron fluorinated compounds, it is crystalline in aubergine；Wherein α:β:γ is 5:7:100；
2) preparation of the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-
The double pyrroles's boron fluorine compounds of δ mmol 8- (3- hydroxyl -4- aminobenzene methyl) and ε mmol 2- hydroxyl -1- naphthaldehyde are put into It in reaction vessel, is dissolved with appropriate dehydrated alcohol, ζ mL glacial acetic acid is added, wherein δ:ε:ζ is 2:2:1；In nitrogen protection Under, reaction mixture is warming up to 75 degree, reacts 3~8 hours, obtains red suspension, the red suspension is cooling, filter, Dehydrated alcohol washing, vacuum drying, obtain the bis- pyrroles's boron fluorine fluorescent molecular probes of naphthaldehyde-.
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Citations (3)

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Publication number Priority date Publication date Assignee Title
CN102627662A (en) * 2012-03-21 2012-08-08 四川大学 Synthesis and cell imaging application of long-wavelength boron fluoride-dipyrrole fluorescent dyes
CN104560010A (en) * 2013-10-18 2015-04-29 茵泰科技(大连)有限公司 Fluorescent probe and application thereof to detection of Fe<2+>
CN107474824A (en) * 2016-06-07 2017-12-15 天津医科大学 Aluminium ion fluorescence probe

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
CN102627662A (en) * 2012-03-21 2012-08-08 四川大学 Synthesis and cell imaging application of long-wavelength boron fluoride-dipyrrole fluorescent dyes
CN104560010A (en) * 2013-10-18 2015-04-29 茵泰科技(大连)有限公司 Fluorescent probe and application thereof to detection of Fe<2+>
CN107474824A (en) * 2016-06-07 2017-12-15 天津医科大学 Aluminium ion fluorescence probe

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HAIPING WANG ET AL.: "A highly selective colorimetric sensor to Fe3+ and Co2+ in aqueous solutions", 《RES CHEM INTERMED》 *

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