CN107033174A - 氟硼荧光染料粘度计及其制备方法和应用 - Google Patents
氟硼荧光染料粘度计及其制备方法和应用 Download PDFInfo
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- 238000006243 chemical reaction Methods 0.000 claims description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
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- 229910052763 palladium Inorganic materials 0.000 claims description 10
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical group C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 2
- IPRJXAGUEGOFGG-UHFFFAOYSA-N N-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1 IPRJXAGUEGOFGG-UHFFFAOYSA-N 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 14
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- 125000000217 alkyl group Chemical group 0.000 abstract 2
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- 125000005843 halogen group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 238000001228 spectrum Methods 0.000 description 10
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- 239000000047 product Substances 0.000 description 6
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006862 quantum yield reaction Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
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- 238000000034 method Methods 0.000 description 4
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- 125000000168 pyrrolyl group Chemical group 0.000 description 3
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- 239000006228 supernatant Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 2
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- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 239000012300 argon atmosphere Substances 0.000 description 1
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- 230000021615 conjugation Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
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- 229960001866 silicon dioxide Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
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- 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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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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Abstract
本发明公开了一种氟硼荧光染料粘度计及其制备方法和应用,其中,所述氟硼荧光染料粘度计的结构如式(Ⅰ)所示,式(Ⅰ)中,R1为H或C1‑C3的烷基;R2为H或C1‑C10的烷基;R3为H或C1‑C3的烷基;X为卤素。该氟硼荧光染料粘度计在不同粘度的溶剂的荧光信号会产生规律性变化,故该氟硼荧光染料粘度计能够作为粘度计使用;另外,该氟硼荧光染料粘度计为水溶性化合物,其可在生物细胞内进行染色分析。即该氟硼荧光染料粘度计在作为粘度探针以及荧光标记等领域具有良好的应用前景,同时其制备方法步骤简单,产率高且原料易得;
Description
技术领域
本发明涉及荧光染料领域,具体地,涉及氟硼荧光染料粘度计及其制备方法和应用。
背景技术
氟硼二吡咯荧光染料(BODIPY)是近二十几年才发展起来的一类光物理化学性能优异的荧光染料分子,具有窄的吸收峰和发射峰、较高的摩尔吸光系数、较高的荧光量子产率、较好的光稳定性以及化学稳定性。普通的荧光染料若对其meso-位置的基团进行限制也会对粘度变化有一定的响应,荧光会发生变化,荧光寿命有时也会改变。
因此,制备出一种更有优异特性的荧光染料粘度计也是具有十分重要的意义。π-分子线在分子电子学和纳米技术等新兴领域有着独特的优势,含有丁二炔的分子线更加能引起人们的兴趣。在这些分子线中,二聚的分子线其实是一种很好的粘度计,可以对其进行修饰,从而得到各种想要的荧光粘度计,以适应不同情况粘度的测量。
发明内容
本发明的目的是提供一种氟硼荧光染料粘度计及其制备方法和应用,该氟硼荧光染料粘度计在不同粘度的溶剂内测得荧光信号不一样,且荧光信号会随着粘度变化呈现规律性的变化;故该氟硼荧光染料粘度计能够作为粘度探针以及在荧光标记领域具有良好的应用前景。同时该制备方法步骤简单,且原料易得。
为了实现上述目的,本发明提供了一种氟硼荧光染料粘度计,其中,所述氟硼荧光染料粘度计的结构如式(Ⅰ)所示,
式(Ⅰ)中,R1为H或C1-C3的烷基;R2为H或C1-C10的烷基;R3为H或C1-C3的烷基;X为卤素。
本发明还提供了一种上述氟硼荧光染料粘度计的制备方法,其中,所述制备方法包括如下步骤:
1)在溶剂存在条件下,将如式(a)所示的化合物与弱碱进行第一接触反应,制得如式(b)所示的化合物;
2)在钯催化剂和铜催化剂的存在下,将如式(b)所示的化合物与4-碘吡啶进行第二接触反应,制得如式(c)所示的化合物;
3)在黑暗条件下,将如式(c)所示的化合物与卤代烃进行第三接触反应,制得如式(Ⅰ)所示的化合物;
R1为H或C1-C3的烷基;R2为H或C1-C10的烷基;R3为H或C1-C3的烷基;X为卤素。
本发明还提供了一种上述氟硼荧光染料粘度计在荧光标记领域中以及作为粘度探针的应用。
通过上述技术方案,本发明通过提供的制备方法制得的氟硼荧光染料粘度计,该氟硼荧光染料粘度计在不同粘度的溶剂的荧光信号会产生规律性变化,故该氟硼荧光染料粘度计能够作为粘度计使用;另外,该氟硼荧光染料粘度计为水溶性化合物,其可在生物细胞内进行染色分析。即该氟硼荧光染料粘度计在作为粘度探针以及荧光标记等领域具有良好的应用前景,同时其制备方法步骤简单,产率高且原料易得。
本发明的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本发明的进一步理解,并且构成说明书的一部分,与下面的具体实施方式一起用于解释本发明,但并不构成对本发明的限制。在附图中:
图1是检测例2中的荧光发射光谱图;
图2是检测例3中的荧光发射光谱图。
具体实施方式
以下对本发明的具体实施方式进行详细说明。应当理解的是,此处所描述的具体实施方式仅用于说明和解释本发明,并不用于限制本发明。
本发明中提供了一种氟硼荧光染料粘度计,其中,所述氟硼荧光染料粘度计的结构如式(Ⅰ)所示,
式(Ⅰ)中,R1为H或C1-C3的烷基;R2为H或C1-C10的烷基;R3为H或C1-C3的烷基;X为卤素。
本发明中,所述R1、R2和R3均可以在宽的范围内选择,但是为了进一步提高所述氟硼荧光染料粘度计的水溶性及其产率,优选地,所述R1为甲基;所述R2为正庚基;所述R3为甲基,所述卤素为碘。
本发明还提供了一种上述氟硼荧光染料粘度计制备方法,其特征在于,所述制备方法包括如下步骤:
1)在溶剂存在条件下,将如式(a)所示的化合物与弱碱进行第一接触反应,制得如式(b)所示的化合物;
2)在钯催化剂和铜催化剂的存在下,将如式(b)所示的化合物与4-碘吡啶进行第二接触反应,制得如式(c)所示的化合物;
3)在黑暗条件下,将如式(c)所示的化合物与卤代烃进行第三接触反应,制得如式(Ⅰ)所示的化合物;
其中,R1为H或C1-C3的烷基;R2为H或C1-C10的烷基;R3为H或C1-C3的烷基;X为卤素。
在上述制备方法中,所述R1、R2和R3均可以在宽的范围内选择,但是为了进一步提高所述氟硼荧光染料粘度计的水溶性及其产率,优选地,所述R1为甲基;所述R2为正庚基;所述R3为甲基,所述卤素为碘。
另外,步骤1)和2)是在溶剂存在下发生反应的,且溶剂种类可以在宽的范围内选择,但是为了促进反应的进行及提高产物的产率,优选地,所述溶剂由溶剂A和溶剂B组成;其中,溶剂A为四氢呋喃,溶剂B为甲醇或乙醇,且溶剂A与溶剂B的体积比为1:1-1.5。
为了促进步骤1)的反应进行,进一步优选地,第二接触反应于四氢呋喃中进行。
为了促进步骤2)的反应进行,进一步优选地,第三接触反应于N,N-二甲基甲酰胺中进行。
为了促进步骤3)的反应进行,第三接触反应于N,N-二甲基甲酰胺中进行。
在发明提供的制备方法中,各原料的用量可以根据实际需要进行调节,在发明的一种优选的实施方式中,为了使产品的转化率较高,进一步降低制备成本,优选地,相对于1mol所述式(a)所示的化合物,所述弱碱的用量为4-15mol,所述4-碘吡啶的用量为2-12mol,所述卤代烃的用量为40-200mol,所述钯催化剂的用量为0.03-0.2mol,所述铜催化剂的用量为0.03-0.2mol。
更为优选地实施方式中,相对于1mol如所述式(a)所示的化合物,所述弱碱的用量为4-8mol,所述4-碘吡啶的用量为2-8mol,所述卤代烃的用量为60-120mol。
所述弱碱可在宽的范围内选择,但是为了进一步提高产品的转化率,降低制备成本,优选地,所述弱碱为碳酸钾、碳酸钠、碳酸氢钠或碳酸氢钾
同时,所述卤代烃的种类可以在宽的范围内选择,但是为了提高反应产率,优选地,所述卤代烃为碘甲烷、溴甲烷或溴丁烷。
另外,本发明中,钯催化剂和铜催化剂的种类可以在宽的范围内选择,但是为了提高反应速率和产品的转换率,优选地,所述钯催化剂为二氯二三苯基磷钯,所述铜催化剂为氯化亚铜。
此外,在本发明中另一种优选地实施方式中使得经过第二接触反应制得的氟硼荧光染料粘度计优异的产率,第二接触反应体系中还包括路易斯碱,且相对于1mol所述式(a)所示的化合物,所述路易斯碱的用量为20-80mol;更优选地,所述路易斯碱的用量为40-60mol。
其中,路易斯碱的具体种类可以在宽的范围内选择,但是为了进一步地提高产率以及从成本上考虑,优选地,所述路易斯碱为三乙胺。
第一接触反应、第二接触反应和第三接触反应的反应条件可以不作进一步限定,当然,在本发明的一种优选的实施方式中,为了使原料的转化率更高,优选地,所述第一接触反应的反应时间为0.5-3h,反应温度为15-40℃;所述第二接触反应的反应时间为0.5-3h,反应温度为20-60℃;所述第三接触反应的反应时间为6-15h,反应温度为25-40℃。
本发明还提供了上述氟硼荧光染料粘度计以及根据上述的方法制备的氟硼荧光染料粘度计在荧光标记以及作为粘度探针等领域中的应用。
以下将通过实施例对本发明进行详细描述,但本发明并不仅限于下述实施例。
以下实施例中,核磁测定采用瑞士Bruker公司的AV-300型核磁共振仪进行;质谱的测定采用美国仪器集团的HPLC/ESI-MS型质谱仪进行;紫外光谱的测定采用日本岛津公司的UV-2450型紫外/可见分光光度计进行,荧光光谱的测定日本日立公司的F-4500FL荧光分光光度计进行,相对荧光量子产率的测定采用荧光光谱的测定日本日立公司的F-4500FL荧光分光光度计进行,单晶衍射的测定采用德国Bruker AXS公司的SMAR APEXⅡX-单晶衍射仪进行,其中λmax表示最大吸收波长、εabs表示摩尔消光系数,λem max表示最大荧光发射波长,ΦF表示相对荧光量子产率和Stokes-shift表示Stokes位移;相对荧光量子产率(ΦF)的测定是以其中相对荧光量子产率ΦF的测定以荧光黄(Φ=0.90,在氢氧化钠溶液中)为标准染料,根据公式ΦF=ΦS*(IX/IS)*(AS/AX)*(nX/nS)2计算所得,其中ΦS为标准物荧光黄的荧光量子产率,I为谱图积分面积,A为吸光度,n为溶剂的折光率,下角标S为标准物,X为待测物。
以下实施例中使用的原料:碳酸钾、甲醇、四氢呋喃、己烷、三乙胺、二氯甲烷、N,N-二甲基甲酰胺是国药集团化学试剂有限公司的产品,碘化亚铜、二氯二三苯基磷化钯、4-碘吡啶、碘甲烷是安耐吉化学公司的产品。
制备例1
将如式(3b-1)所示结构的原料(108mg,0.2mmol),CuCl(160mg,1.6mmol)加入到小试管内,然后加入1ml干燥的N,N-二甲基甲酰胺,放在60℃下反应2小时。将反应液倒入水中,用二氯甲烷萃取,用无水硫酸钠干燥后,减压蒸馏,而后再用硅胶柱层析制得如式(a’)所示结构的化合物(摩尔产率为37%),有7%的原料未反应完。
对上述如式(a’)所示结构的化合物进行核磁氢谱和核磁碳谱检测:
1H NMR(500MHz,CDCl3)δ:2.98(t,J=7.8Hz,4H),2.65(s,6H),2.61(s,6H),2.54(s,6H),2.52(s,6H),1.66-1.58(m,4H),1.52-1.49(m,4H),1.37-1.27(m,12H),0.90(t,J=6.8Hz,6H),0.26(s,18H);13C NMR(75MHz,CDCl3)δ:158.0,157.6,148.2,142.7,142.5,131.5,130.9,116.8,114.7,102.1,97.1,80.7,75.6,31.8,31.7,30.2,29.0,28.8,22.6,15.1,14.1,14.0,13.7,13.5;HRMS(APCI)Calcd.for C54H73B2F4N4Si2[M+H]+:931.5491,found:931.5451。
制备例2
如式(b’)所示结构的原料的制备:将如式(a’)所示结构的原料(93mg,0.1mmol)溶解在6ml的甲醇和6ml的四氢呋喃里,然后加入碳酸钾(83mg,0.6mmol),在20℃条件下搅拌1小时。反应完全后将反应液倒入稀盐酸水溶液中,用二氯甲烷萃取,用无水硫酸钠干燥后,减压蒸馏,而后再用硅胶柱层析制得如式(b’)所示结构的化合物(产率为92%)。
对上述如式(b’)所示结构的化合物进行核磁氢谱和核磁碳谱检测:1H NMR(500MHz,CDCl3)δ:3.40(s,2H),2.99(t,J=8.0Hz,4H),2.66(s,6H),2.63(s,6H),2.55(s,6H),2.53(s,6H),1.67-1.59(m,4H),1.53-1.51(m,4H),1.37-1.30(m,12H),0.90(t,J=6.5Hz,6H);13C NMR(125MHz,CDCl3)δ:158.0,157.8,148.4,143.1,142.9,131.4,131.0,115.5,114.8,84.4,80.6,76.0,75.5,31.8,31.7,30.3,29.0,28.9,22.6,15.3,15.1,14.1,13.7,13.5。
制备例3
如式(c’)所示结构的原料的制备:将如式(b’)所示结构的原料(79mg,0.1mmol),4-碘吡啶(123mg,0.6mmol),Pd(PPh3)2Cl2(7mg,0.01mmol)和CuI(2mg,0.01mmol)加入到Schlenk瓶内,抽真空通氩气三次,在通氩气氛围下将5ml四氢呋喃和0.5ml三乙胺加入瓶内,在40℃氩气氛围下反应1小时,反应完全后将反应液经过一个短硅胶柱,除去不溶的催化剂,减压蒸馏,而后再用硅胶柱层析制得如式(c’)所示结构的的化合物(产率为81%)。
对上述如式(c’)所示结构的的化合物进行核磁氢谱和核磁碳谱检测:1H NMR(500MHz,CDCl3)δ:8.61(d,J=5.0Hz,4H),7.38(d,J=5.0Hz,4H),3.02(t,J=8.3Hz,4H),2.69(s,6H),2.68(s,6H),2.59(s,6H),2.57(s,6H),1.85-1.75(m,4H),1.64-1.63(m,4H),1.38-1.29(m,12H),0.91(t,J=7.5Hz,6H);13C NMR(125MHz,CDCl3)δ:158.6,157.3,149.8,148.6,143.4,142.3,131.6,131.5,131.3,125.1,115.2,94.1,86.7,80.9,75.5,31.9,31.7,30.3,29.1,29.0,22.6,15.3,15.2,14.1,13.8,13.7。
实施例1
如式(I’)所示的氟硼荧光染料粘度计的制备:将如式(c’)所示结构的化合物(19mg,0.02mmol)加入到小试管内,然后加入1ml N,N-二甲基甲酰胺,再加入碘甲烷(125μL,2mmol),放在30℃黑暗条件下反应10小时。反应完成后在反应液上面铺一层乙醚将产物重结晶沉淀出来,然后进行离心,倒掉上清液即可得到如式(I’)所示的氟硼荧光染料粘度计(产率为91%)。
对上述如式(I’)所示的氟硼荧光染料粘度计进行核磁氢谱、核磁碳谱检测:1HNMR(500MHz,DMSO-d6)δ:8.97(d,J=7.0Hz,4H),8.23(d,J=7.0Hz,4H),4.29(s,6H),3.09(t,J=5.0Hz,4H),2.66-2.65(m,12H),2.60-2.58(m,12H),1.65-1.63(m,4H),1.55-1.53(m,4H),1.40-1.38(m,4H),1.32-1.30(m,8H),0.89(t,J=6.5Hz,6H);13C NMR(125MHz,DMSO-d6)δ:159.2,157.4,150.7,145.7,144.4,138.8,132.0,131.7,131.5,128.6,115.1,113.5,96.2,93.8,81.1,76.0,48.0,31.6,31.4,30.0,28.9,28.7,22.5,15.6,15.4,14.3,14.0,13.8。
实施例2
按照实施例1的方法:将如式(c’)所示结构的化合物(19mg,0.02mmol)加入到小试管内,然后加入1ml N,N-二甲基甲酰胺,再加入碘甲烷(125μL,2mmol),放在35℃黑暗条件下反应12小时。反应完成后在反应液上面铺一层乙醚将产物重结晶沉淀出来,然后进行离心,倒掉上清液即可得到如式(I’)所示的氟硼荧光染料粘度计(产率为91%)。
实施例3
按照实施例1的方法:将如式(c’)所示结构的化合物(19mg,0.02mmol)加入到小试管内,然后加入1ml N,N-二甲基甲酰胺,再加入碘甲烷(125μL,2mmol),放在40℃黑暗条件下反应15小时。反应完成后在反应液上面铺一层乙醚将产物重结晶沉淀出来,然后进行离心,倒掉上清液即可得到如式(I’)所示的氟硼荧光染料粘度计(产率为91%)。
测试例1
将上述制备例1-3制得的原料(a’)、(b’)、(c’)和实施例1中制得的氟硼荧光染料粘度计(I’)分别检测其在不同溶剂中的光谱性质,测试结果如表1所示:
表1
表1中:Stokes-shift=λem max-λmax(nm)。
检测例2
将实施例1中制备的如式(I’)所示结构的粘度计在乙醇和丙三醇不同体积比溶剂中的荧光发射光谱图,结构见图1所示;其中图1中所标数字为乙醇、丙三醇不同比例下所对应的溶液的粘度数值。
图1中,随着粘度的增加,氟硼荧光染料粘度计中两个氟硼二吡咯单元绕中间的丁二炔旋转速度变慢,其共平面性在减弱,相互扭曲的构象在增加。所得荧光光谱中长波峰的强度在降低,短波峰的强度在增加。
检测例3
将实施例1中制备的如式(I’)所示结构的氟硼荧光染料粘度计在丙三醇与乙醇的体积比为9:1的混合溶剂中,测试不同温度的荧光发射光谱图,结果见图2所示,图2中所标数值为测时溶剂的温度数值。
图2中,随着温度的升高,混合溶剂的粘度数值在降低,此时测试的荧光光谱也发生改变,进一步说明本发明提供的氟硼荧光染料粘度计在测量粘度变化方面具有良好的应用价值。
通过上述图1和图2可知,本发明制得的氟硼荧光染料粘度计在乙醇里的最大荧光发射波长在624nm,说明其两边的氟硼二吡咯单元在低粘度介质中处于共平面位置,共轭比较好,荧光发射波长比较长;当增加介质的粘度时,粘度计中两个氟硼二吡咯单元绕中间的丁二炔旋转的速度变慢,染料分子的平面性受到破坏,共轭效果降低,导致荧光发射波长蓝移。同时该氟硼荧光染料粘度计还具有水溶性,其可在生物细胞内进行染色分析。说明其在荧光标记以及作为粘度探针等领域具有良好的应用前景,同时该制备方法步骤简单,产率高且原料易得。
同样,对上述实施例2-3所制得的如式(I’)所示的氟硼荧光染料粘度计进行核磁氢谱、核磁碳谱检测,其结果与实施例1的检测结果基本一致;并对实施里2-3制得的如式(I’)所示的氟硼荧光染料粘度计进行检测例1-3的检测,其检测结果也与实施例1的检测结果基本一致。
所示实施例仅用于描述本发明的概要,并不限制本发明,技术员可在所属领域自主选择实施。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于上述实施方式中的具体细节,在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,这些简单变型均属于本发明的保护范围。
另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合,为了避免不必要的重复,本发明对各种可能的组合方式不再另行说明。
此外,本发明的各种不同的实施方式之间也可以进行任意组合,只要其不违背本发明的思想,其同样应当视为本发明所公开的内容。
Claims (10)
1.一种氟硼荧光染料粘度计,其特征在于,所述氟硼荧光染料粘度计的结构如式(Ⅰ)所示,
式(Ⅰ)中,R1为H或C1-C3的烷基;R2为H或C1-C10的烷基;R3为H或C1-C3的烷基;X为卤素。
2.根据权利要求1所述的氟硼荧光染料粘度计,其中,所述R1为甲基;所述R2为正庚基;所述R3为甲基,所述卤素为碘。
3.一种如权利要求1或2所述的氟硼荧光染料粘度计的制备方法,其特征在于,所述制备方法包括如下步骤:
1)在溶剂存在条件下,将如式(a)所示的化合物与弱碱进行第一接触反应,制得如式(b)所示的化合物;
2)在钯催化剂和铜催化剂的存在下,将如式(b)所示的化合物与4-碘吡啶进行第二接触反应,制得如式(c)所示的化合物;
3)在黑暗条件下,将如式(c)所示的化合物与卤代烃进行第三接触反应,制得如式(Ⅰ)所示的化合物;
其中,R1为H或C1-C3的烷基;R2为H或C1-C10的烷基;R3为H或C1-C3的烷基;X为卤素。
4.根据权利要求3所述的制备方法,其中,所述R1为甲基,所述R2为正庚基,所述R3为甲基。
5.根据权利要求3所述的制备方法,其中,所述溶剂由溶剂A和溶剂B组成;所述溶剂A为四氢呋喃,所述溶剂B为甲醇或乙醇,且所述溶剂A与溶剂B的体积比为1:1-1.5;
优选地,所述第二接触反应于四氢呋喃中进行;
优选地,所述第三接触反应于N,N-二甲基甲酰胺中进行。
6.根据权利要求3-5中任意一项所述的制备方法,其中,相对于1mol所述式(a)所示的化合物,所述弱碱的用量为4-15mol,所述4-碘吡啶的用量为2-12mol,所述卤代烃的用量为40-200mol,所述钯催化剂的用量为0.03-0.2mol,所述铜催化剂的用量为0.03-0.2mol;
优选地,相对于1mol如所述式(a)所示的化合物,所述弱碱的用量为4-8mol,所述4-碘吡啶的用量为2-8mol,所述卤代烃的用量为60-120mol。
7.根据权利要求6所述的制备方法,其中,所述弱碱为碳酸钾、碳酸钠、碳酸氢钠或碳酸氢钾,所述卤代烃为碘甲烷、溴甲烷或溴丁烷;
优选地,所述钯催化剂为二氯二三苯基磷钯,所述铜催化剂为氯化亚铜。
8.根据权利要求7所述的制备方法,其中,所述第二接触反应的体系中还包括路易斯碱;相对于1mol所述式(a)所示的化合物,所述路易斯碱的用量为20-80mol;
优选地,所述路易斯碱的用量为40-60mol;
更为优选地,所述路易斯碱为三乙胺。
9.根据权利要求8所述的制备方法,其中,所述第一接触反应的反应时间为0.5-3h,反应温度为15-40℃;
优选地,所述第二接触反应的反应时间为0.5-3h,反应温度为20-60℃;
更为优选地,所述第三接触反应的反应时间为6-15h,反应温度为25-40℃。
10.一种如权利要求1或2所述的如式(Ⅰ)所示的氟硼荧光染料粘度计在荧光标记领域中以及作为粘度探针的应用。
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