CN106749365A - A kind of H2S detection reagents and its synthetic method and application - Google Patents
A kind of H2S detection reagents and its synthetic method and application Download PDFInfo
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- 238000001514 detection method Methods 0.000 title claims abstract description 24
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 15
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 11
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 11
- 238000012360 testing method Methods 0.000 claims abstract description 10
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 70
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 238000002390 rotary evaporation Methods 0.000 claims description 8
- 239000000523 sample Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 238000012417 linear regression Methods 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 6
- 239000007832 Na2SO4 Substances 0.000 claims description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical class OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003053 piperidines Chemical class 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 239000012488 sample solution Substances 0.000 claims description 2
- 238000007171 acid catalysis Methods 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 claims 1
- 230000001186 cumulative effect Effects 0.000 claims 1
- 239000002027 dichloromethane extract Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 1
- 150000003233 pyrroles Chemical class 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 abstract 3
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical class COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 abstract 1
- VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 33
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 16
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- YAVVGPBYBUYPSR-UHFFFAOYSA-N benzene;oxygen Chemical compound [O].C1=CC=CC=C1 YAVVGPBYBUYPSR-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- MFFMQGGZCLEMCI-UHFFFAOYSA-N 2,4-dimethyl-1h-pyrrole Chemical class CC1=CNC(C)=C1 MFFMQGGZCLEMCI-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000191368 Chlorobi Species 0.000 description 1
- 241000190834 Chromatiaceae Species 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- OSVXSBDYLRYLIG-UHFFFAOYSA-N chlorine dioxide Inorganic materials O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- TVWHTOUAJSGEKT-UHFFFAOYSA-N chlorine trioxide Chemical compound [O]Cl(=O)=O TVWHTOUAJSGEKT-UHFFFAOYSA-N 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- -1 dichloromethane 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound 0.000 description 1
- ITXWZEJLEWKPAF-UHFFFAOYSA-N dichloromethane 1H-pyrrole Chemical class ClCCl.N1C=CC=C1 ITXWZEJLEWKPAF-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical class C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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Abstract
The invention provides a kind of H2S detection reagents and its synthetic method and application, the detection reagent are (E) 4 (4 (2 (5,5 difluoro 10 (4 methoxyphenyl) 1,7,9 trimethyl 5H 4,5, two pyrrolo- [1,2 c：2', 1'f] base of [1,3,2] diaza boron ring triolefin 3) vinyl) phenoxy group) 7 nitro benzo [c] [1,2,5] oxadiazoles (BDP N1).Tube- nursery method：(5,5 difluoro 10 (4 methoxyphenyl) 3,7,9 trimethyl 5H 4,5, two pyrrolo-es [1,2 c is obtained by raw material of 4 methoxybenzaldehydes：2', 1'f] 2] base of diaza boron ring triolefin 1) methyl；(E) 4 (2 (5,5 difluoro 10 (4 methoxyphenyl) 1,7,9 trimethyl 5H 4,5, two pyrrolo-es [1,2 c are obtained by condensation reaction with 4 hydroxy benzaldehydes again：2'f] base of [1,3,2] diaza boron ring triolefin 3) vinyl) phenol；BDP N1 are obtained by substitution reaction with the diazole of 4 chlorine, 7 nitro benzo, 2 oxa- 1,3 again.The invention provides detection H2The method of S, the method sensitivity is high, and selectivity is good, and detection process is easy, testing result is accurate.
Description
Technical field
The present invention relates to sulfurated hydrogen detection technology, and in particular to (E) -4- (4- (2- (5,5- bis- fluoro- 10- (4- methoxybenzenes
Base) -1,7,9- trimethyls -5H-4,5,-two pyrrolo- [1,2-c：2', 1'-f] [1,3,2] diaza boron ring triolefin -3- bases) second
Alkenyl) phenoxy group) -7- nitros benzo [c] [1,2,5] oxadiazoles (BDP-N1) and its synthetic method, and BDP-N1 is used as examination
Application of the agent in hydrogen sulfide is detected.
Background technology
Sour gas with addled egg smell when hydrogen sulfide is a kind of colourless, inflammable, soluble in water, low concentration, to eye
There is stimulation with respiratory tract.Hydrogen sulfide is widely present in the crude oil in nature, natural gas, volcanic gas and hot spring, in life
Played an important role in thing geochemical cycle, be also the significant energy source of the microorganisms such as purple and green sulfur bacteria.For many years
Come, hydrogen sulfide is considered as always poisonous, environmentally harmful gas.But in recent years, increasing research find it
Also it is widely present in mammal body including humans, and plays important biological action.H2S have been considered to after
The third gaseous signal molecule after nitric oxide (NO) and carbon monoxide (CO), with different physiological roles, including modulation
Blood pressure, alleviates ischemic damage and reperfusion damage, plays antiinflammatory action, regulation Cellular Oxidation stress pressure, reduce metabolic rate etc..Sulphur
The change for changing hydrogen level is related to various diseases, such as Down syndrome and Alzheimer's and angiocardiopathy.
Up to the present, there are many methods for detecting internal and external concentration of hydrogen sulfide, such as：Methylene blue laws,
Gas-chromatography and small-molecule fluorescent probe.Wherein, small-molecule fluorescent probe detection due to its have high sensitivity, high selectivity,
Noninvasive, easy to operate and real time imagery feature have been considered to be most promising detection technique.
In the present invention, design has synthesized (E) -4- (4- (2- (5,5- bis- fluoro- 10- (4- methoxyphenyls) -1,7,9- tri-
Methyl -5H-4,5,-two pyrrolo- [1,2-c：2', 1'-f] [1,3,2] diaza boron ring triolefin -3- bases) vinyl) benzene oxygen
Base) -7- nitros benzo [c] [1,2,5] oxadiazoles (BDP-N1), by H2The change of fluorescence intensity before and after the thioclastic reaction of S, it is real
Existing H2The detection of S.
The content of the invention
It is an object of the invention to provide a kind of H2S detection reagents and its synthetic method, and the detection reagent is used to determine
Amount detection H2S, and easy to operate during detection, selective high, sensitivity is high.
A kind of H that the present invention is provided2S detection reagents, are (E) -4- (4- (2- (5,5- bis- fluoro- 10- (4- methoxybenzenes
Base) -1,7,9- trimethyls -5H-4,5,-two pyrrolo- [1,2-c:2', 1'-f] [1,3,2] diaza boron ring triolefin -3- bases) second
Alkenyl) phenoxy group) -7- nitros benzo [c] [1,2,5] oxadiazoles (BDP-N1), English name：(E)-4-(4-(2-(5,5-
difluoro-10-(4-methoxyphenyl)-1,7,9-trimethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',
1'-f][1,3,2]diazaborinin-3-yl)vinyl)phenoxy)-7-nitrobenzo[c][1,2,5]
Oxadiazole, structural formula is：
The synthetic method of BDP-N1, step is：
1) in N2Under protection, 4-methoxybenzaldehyde (1eq.), 2,4- dimethyl pyrroles are added toward dichloromethane
A few drop trifluoroacetic acids are instilled under (2eq.), stirring condition, 6-8h is stirred at room temperature；It is subsequently adding the 2,3- being dissolved in dichloromethane
Two chloro- 5,6- dicyanos-Isosorbide-5-Nitrae-benzoquinones (1eq.) solution, are stirred for 4-5h；Excess of triethylamine is added, after 15-20min, at 0 DEG C
Under, excessive boron trifluoride ether solution is added dropwise, then heat to room temperature and be stirred for 6-8h reaction completions.Reaction solution is poured into water
In, extracted with dichloromethane, merge organic phase, add Na2SO4Water removal, then removes dichloromethane rotary evaporation, Ran Houzhu
Chromatographic isolation (petroleum ether：Dichloromethane=4:1) orange red solid is obtained.
2) in N2Under protection, previous step product (1eq.), 4- hydroxy benzaldehydes (1eq.) are catalyzed in piperidines and glacial acetic acid
Under in reflux in toluene 4-6h, be cooled to rotary evaporation after room temperature and remove toluene, by reactant mixture pillar layer separation (wash-out
Agent is petroleum ether：Ethyl acetate=7:5) brown-red solid is obtained.
3) in ethanol in proper amount, previous step product (1.eq.), chloro- 7- nitros benzo -2- oxa- -1 of 4-, 3- diazole are added
(1eq.) triethylamine (1.5eq.) is stirred 12-14 hours at room temperature, is then poured into water reaction solution and is extracted with dichloromethane,
Organic phase is washed with sodium chloride solution, anhydrous Na is then used2SO4Then water removal, suction filtration removes dichloromethane rotary evaporation, remains
(eluant, eluent is petroleum ether to remaining solid pillar layer separation：Ethyl acetate：Dichloromethane=4：1：1).
A kind of quick detection H that the present invention is provided2The method of S, is (E) -4- (4- (2- (5,5- bis- fluoro- 10- (4- methoxies
Base phenyl) -1,7,9- trimethyls -5H-4,5,-two pyrrolo- [1,2-c:2', 1'-f] [1,3,2] diaza boron ring triolefin -3-
Base) vinyl) phenoxy group) -7- nitros benzo [c] [1,2,5] oxadiazoles (BDP-N1), it is quantitative in the PBS solution that pH is 7.4
Ground detection H2The content of S；Concretely comprise the following steps：
(1) it is the PBS cushioning liquid of 10mM, to prepare pH=7.4, concentration, prepares the DMSO solution of the BDP-N1 of 2mM；
(2), by the DMSO solution of the PBS cushioning liquid of 1600 μ L pH 7.4,400 μ L DMSO solutions and 5 μ L BDP-N1
It is added in fluorescence cuvette, is detected on Fluorescence spectrophotometer, with the addition for treating test sample, the fluorescence intensity of 587nm is gradually
Enhancing；
(3), by the DMSO solution of the PBS cushioning liquid of 1600 μ L pH 7.4,400 μ L DMSO solutions and 5 μ L BDP-N1
It is added in other six fluorescence cuvettes, the H that volume is 0,10,20,30,40,50 μ L is added respectively2S solution, in fluorescence point
It is 17,531,1161,1589,2155,2559 that the corresponding fluorescence intensity F of 587nm are determined on light photometer, with H2S concentration is horizontal stroke
Coordinate, is drawn as ordinate with fluorescence intensity F and schemed, and obtains H2The working curve of S concentration；Equation of linear regression is：F=
The unit of 51.64c-46.20, c for μM；
(4), by the PBS cushioning liquid of 1600 μ L pH 7.4 and the DMSO solution of 400 μ L DMSO solutions and 5 μ LBDP-N1
It is added in clean fluorescence cuvette, V μ L testing sample solutions is drawn with microsyringe, is added in this fluorescence cuvette,
Detected on Fluorescence spectrophotometer, the fluorescence intensity that will be measured substitutes into the equation of linear regression of step (3), obtains concentration c, treats
Test sample product CTreat test sample=2000 μ L × c × 10-6/ V μ L, can try to achieve H2The concentration of S.
The detection method is to H2S shows sensitivity and selectivity high, and detection process is easy, testing result is accurate.
Compared with prior art, the invention has the advantages that and effect：1st, tube- nursery is simple, detection architecture low cost
It is honest and clean；2nd, detection method of the invention, to H2S shows sensitivity and selectivity high；3rd, detection means is simple, it is only necessary to by
Fluorescence spectrophotometer is to be capable of achieving.
Brief description of the drawings：
The nucleus magnetic hydrogen spectrum figure of BDP-N1 prepared by Fig. 1 embodiments 1
The nuclear-magnetism carbon spectrogram of BDP-N1 prepared by Fig. 2 embodiments 1
The mass spectrogram of BDP-N1 prepared by Fig. 3 embodiments 1
The reagent of Fig. 4 embodiments 2 and H2The fluorescent emission figure of S effects
The fluorescence block diagram of the reagent of Fig. 5 embodiments 3 and various analytes
Fig. 6 embodiments 4 determine H2The working curve of S
The fluorescent emission figure of the determination sample of Fig. 7 embodiments 5
Specific embodiment：
Embodiment 1 (E) -4- (4- (2- (5,5- bis- fluoro- 10- (4- methoxyphenyls) -1,7,9- trimethyl -5H-4,5, -
Two pyrrolo- [1,2-c：2', 1'-f] [1,3,2] diaza boron ring triolefin -3- bases) vinyl) phenoxy group) -7- nitro benzos
The synthesis of [c] [1,2,5] oxadiazoles (BDP-N1) and sign.
1) in N2Under protection, 4-methoxybenzaldehyde (3mmol, 0.408g), 2,4- dimethyl are added toward dichloromethane
Pyrroles (6mmol, 0.855g), instills a few drop trifluoroacetic acids under stirring condition, 6h is stirred at room temperature；It is subsequently adding and is dissolved in dichloromethane
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (3mmol, 0.68g) solution in alkane, is stirred for 4h；9mL triethylamines are added,
After 15min, at 0 DEG C, 9mL boron trifluoride ether solutions are added dropwise, then heat to room temperature and be stirred for 6-8h reaction completions.Anti-
Answer liquid to be poured into water, extracted with dichloromethane, merge organic phase, add Na2SO4Water removal, then rotates dichloromethane evaporation and removes
Go, then pillar layer separation (petroleum ether：Dichloromethane=4:1) orange red solid (fluoro- 10- (the 4- methoxybenzenes of 5,5- bis- are obtained
Base) -3,7,9- trimethyls -5H--4,5,-two pyrrolo- [1,2-c：2', 1'-f] 2] diaza boron ring triolefin -1- bases) methyl
0.356g, yield:33%.
2) in N2Under protection, by previous step product (0.5mmol, 0.177g), 4- hydroxy benzaldehydes (0.5mmol,
0.074g) in reflux in toluene 4h under 0.3mL piperidines and the catalysis of 0.3mL glacial acetic acids, rotary evaporation is removed after being cooled to room temperature
Toluene, by reactant mixture pillar layer separation, (eluant, eluent is petroleum ether：Dichloromethane=7:5) obtain brown-red solid (E)-
4- (2- (fluoro- 10- (4- the methoxyphenyls) -1,7,9- trimethyls of 5,5- bis- -5H-4,5,-two pyrrolo- [1,2-c：2'f][1,
3,2] diaza boron ring triolefin -3- bases) vinyl) phenol 0.05g, yield：10.2%,.
3) in ethanol in proper amount, previous step compound (0.1mmol, 0.045g), the chloro- 7- nitros benzo -2- oxygen of 4- are added
Miscellaneous -1,3- diazole (0.1mmol, 0.02g), and triethylamine (0.15mmol, 105 μ L) stirs 12-14 hours at room temperature, then
Reaction solution is poured into water and is extracted with dichloromethane, organic phase is washed with sodium chloride solution, then use anhydrous Na2SO4Water removal,
Suction filtration, then removes dichloromethane rotary evaporation, and (eluant, eluent is petroleum ether to remaining solid pillar layer separation：Ethyl acetate：
Dichloromethane=4：1：1) target compound (E) -4- (4- (2- (5,5- bis- fluoro- 10- (4- methoxyphenyls) -1,7,9- are obtained
Trimethyl -5H-4,5,-two pyrrolo- [1,2-c：2', 1'-f] [1,3,2] diaza boron ring triolefin -3- bases) vinyl) benzene oxygen
Base) -7- nitros benzo [c] [1,2,5] oxadiazoles (BDP-N1) 0.0305g, yield：36%.1H NMR(600MHz,
acetone-d6.):δ 8.72 (d, J=6Hz, 2H), 7.89 (d, J=6Hz, 2H), 7.76 (s, 1H), 7.73 (s, 1H), 7.62
(s, 1H), 7.59 (s, 1H), 7.56 (d, J=6Hz, 2H), 7.40 (d, J=12Hz, 2H), 7.23 (d, J=12Hz, 2H),
(s, the 3H) of 6.98 (d, J=6Hz, 1H), 6.23 (s, 1H), 3.95 (s, 3H), 2.60 (s, 3H), 1.57 (s, 3H), 1.54 (figures
1)13C NMR(150MHz,acetone-d6):δ160.63,153.61,151.49,145.69,144.65,135.62,
134.00,129.45,126.60,121.55,119.91,117.56,114.68,109.47,54.86,13.91. (Fig. 2) ESI-
MS m/z:[M+H]+calcd for 623.20；Found 623.20. (Fig. 3)
Embodiment 2
It is the PBS cushioning liquid of 10mM to prepare pH=7.4, concentration, and the solution of 2mM BDP-N1 is prepared with DMSO；
The PBS-DMSO (4 of 2mL:1, pH 7.4) DMSO solution of solution and 5 μ L BDP-N1 is added in fluorescence cuvette, takes H2S's is molten
Liquid, is gradually added in this cuvette with microsyringe, is detected on Fluorescence spectrophotometer in sample-adding, with HS-Plus
Enter, fluorescence intensity gradually strengthens at 587nm.Fluorescent emission figure is shown in Fig. 4.
Embodiment 3
It is the PBS cushioning liquid of 10mM to prepare pH=7.4, concentration, and the BDP-N1 solution of 2mM is prepared with DMSO；22
In individual fluorescence cuvette, the PBS-DMSO (4 of each addition 2mL:1, pH 7.4) DMSO solution of the reagent of solution and 5 μ L, then divide
50 μ L H are not added2S, and 500 μ L various analytes：F-,Cl-,Br-,I-,CN-,NO3 -,NO2 -SO3 2-,SCN-,AcO-,
CO3 2-,SO4 2-,ClO2 -,ClO3 -,ClO4 -,HS-,CO3 2-,PO4 3-,HCO3 -Cys, Hcy and GSH are examined on Fluorescence spectrophotometer
Survey, the block diagram of the corresponding 587nm relative intensity of fluorescence of the different analytes of drafting, (see Fig. 5).HS-So that the fluorescence of reagent is strong
Degree changes to 2559 by 17, and other analytes do not cause the change of reagent fluorescence intensity substantially.
The experiment proved that, other analytes not interference system to H2The measure of S.
Embodiment 4
It is the PBS cushioning liquid of 10mM to prepare pH=7.4, concentration, and the BDP-N1 solution of 2mM is prepared with DMSO, with steaming
Distilled water prepares the NaHS solution of 20mM；2mL PBS-DMSO (4:1, pH 7.4) DMSO solution of the reagent of solution and 5 μ L adds
To in fluorescence cuvette, the HS that volume is 0,10,20,30,40,50 μ L is added respectively-Solution, on Fluorescence spectrophotometer
It is 17,531,1161,1589,2155,2559 to determine the corresponding fluorescence intensity F of 587nm, with H2S concentration is abscissa, with fluorescence
Intensity F is that ordinate draws figure, obtains H2The working curve (see Fig. 6) of S concentration；Equation of linear regression is：F=51.64c-
46.20, c unit for μM；
Embodiment 5
PBS (10mM) cushioning liquid of pH=7.4 is prepared, the NaHS aqueous solution of 20mM is prepared, and prepare 2mM's with DMSO
BDP-N1 solution；The PBS-DMSO (4 of 2mL:1, pH 7.4) DMSO solution of the BDP-N1 of solution and 5 μ L is added to clean glimmering
In light cuvette, the μ L of solution 40 of NaHS are taken, be added in this cuvette with microsyringe, while being determined on XRF
The corresponding fluorescence intensity F of 587nm is 2014.5, by the equation of linear regression of embodiment 4, tries to achieve c=3.8954 × 10- 5Mol/L, deviation is 0.26%.See Fig. 7.
Claims (3)
1. a kind of H2S detection reagents, are characterised by, its be (E) -4- (4- (2- (5,5- bis- fluoro- 10- (4- methoxyphenyls) -1,
7,9- trimethyls -5H-4,5,-two pyrrolo- [1,2-c：2', 1'-f] [1,3,2] diaza boron ring triolefin -3- bases) vinyl)
Phenoxy group) -7- nitros benzo [c] [1,2,5] oxadiazoles (BDP-N1), structural formula is：
2. a kind of H as claimed in claim 12The synthetic method of S detection reagents, it is characterised in that step is：
1) in N2Under protection, the 4-methoxybenzaldehyde of 1 molar equivalent, 2, the 4- diformazans of 2 molar equivalents are added toward dichloromethane
A few drop trifluoroacetic acids are instilled under base pyrroles, stirring condition, 6-8h is stirred at room temperature；Be subsequently adding 1 molar equivalent is dissolved in dichloro
DDQ solution in methane, is stirred for 4-5h；Excess of triethylamine is added, after 15-20min, at 0 DEG C, excessive boron trifluoride is added dropwise
Diethyl ether solution, then heats to room temperature and is stirred for 6-8h reaction completions.Reaction solution is poured into water, is extracted with dichloromethane, closed
And organic phase, add anhydrous Na2SO4Water removal, then removes dichloromethane rotary evaporation, and then pillar layer separation obtains orange
Color solid (fluoro- 10- (4- the methoxyphenyls) -3,7,9- trimethyls of 5,5- bis- -5H--4,5,-two pyrrolo- [1,2-c：2', 1'-
F] 2] diaza boron ring triolefin -1- bases) methyl；
2) in N2Under protection, by the previous step product of 1 molar equivalent, the 4- hydroxy benzaldehydes of 1 molar equivalent, in piperidines and ice second
In reflux in toluene 4-6h under acid catalysis, rotary evaporation removes toluene after being cooled to room temperature, by reactant mixture column chromatography point
From obtaining brown-red solid (E) -4- (2- (fluoro- 10- (4- the methoxyphenyls) -1,7,9- trimethyls of 5,5- bis- -5H-4,5,-two
Pyrrolo- [1,2-c：2'f] [1,3,2] diaza boron ring triolefin -3- bases) vinyl) phenol；
3) in ethanol in proper amount, the compound obtained in the previous step of 1 molar equivalent, the chloro- 7- nitrobenzene of 4- of 1 molar equivalent are added
And -2- oxa- -1,3- diazole, the triethylamine of 1.5 molar equivalents, stir 12-14 hours at room temperature, reaction solution is then poured into water
In and with dichloromethane extract, organic phase is washed with sodium chloride solution, then use anhydrous Na2SO4Water removal, suction filtration, then by dichloro
Methane rotary evaporation is removed, and remaining solid pillar layer separation obtains target compound (E) -4- (4- (2- (5,5- bis- fluoro- 10-
(4- methoxyphenyls) -1,7,9- trimethyls -5H-4,5,-two pyrrolo- [1,2-c：2', 1'-f] [1,3,2] diaza boron ring
Triolefin -3- bases) vinyl) phenoxy group) -7- nitros benzo [c] [1,2,5] oxadiazoles.
3. it is a kind of to detect H2The method of S, it is characterised in that step is：
(1) it is the PBS cushioning liquid of 10mM, to prepare pH=7.4, concentration, prepares the DMSO solution of the BDP-N1 of 2mM；
(2), the DMSO solution of the PBS cushioning liquid of 1600 μ L pH 7.4,400 μ L DMSO solutions and 5 μ L BDP-N1 is added to
In clean fluorescence cuvette, detected on Fluorescence spectrophotometer, with the addition for treating test sample, the fluorescence intensity of 587nm by
It is cumulative strong；
(3), the DMSO solution of the PBS cushioning liquid of 1600 μ L pH 7.4,400 μ L DMSO solutions and 5 μ L BDP-N1 is added to
In other six fluorescence cuvettes, the HS that volume is 0,10,20,30,40,50 μ L is added respectively-Solution, in fluorescence spectrophotometer light
It is 17,531,1161,1589,2155,2559 that the corresponding fluorescence intensity F of 587nm are determined on degree instrument, with H2S concentration is abscissa,
Drawn as ordinate with fluorescence intensity F and schemed, obtain H2The working curve of S concentration；Equation of linear regression is：F=51.64c-
46.20, c unit for μM；
(4), the DMSO solution of the PBS cushioning liquid of 1600 μ L pH 7.4,400 μ L DMSO solutions and 5 μ L BDP-N1 is added to
In clean fluorescence cuvette, V μ L testing sample solutions are drawn with microsyringe, be added to this clean fluorescence cuvette
In, being detected on Fluorescence spectrophotometer, the fluorescence intensity that will be measured substitutes into the equation of linear regression of step (3), obtains concentration
C, testing sample CTreat test sample=2000 μ L × c × 10-6/ V μ L, can try to achieve H2The concentration of S.
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| CN108760697A (en) * | 2018-05-23 | 2018-11-06 | 山西大学 | A kind of two azole derivatives BDP-N of fluorine boron3And its preparation method and use |
| CN109053778A (en) * | 2018-06-14 | 2018-12-21 | 忻州师范学院 | The reagent and its synthetic method of specific detection cyanogen root and application |
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| CN108760697A (en) * | 2018-05-23 | 2018-11-06 | 山西大学 | A kind of two azole derivatives BDP-N of fluorine boron3And its preparation method and use |
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| CN108760697B (en) * | 2018-05-23 | 2020-11-10 | 山西大学 | BODIPY derivative BDP-N3And synthesis method and application thereof |
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