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Boron fluoride dipyrrole fluorescent dye containing hydrophilic groups and preparation method thereof
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A technology of fluoroborate dipyrromethene and dyes, which is applied in the field of dyes to achieve the effects of high yield, sharp peak shape and high strength
Inactive Publication Date: 2014-06-18
TIANJIN UNIV
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However, the lack of water solubility limits its application in the biological field. So far, only a small part of fluorobodipyrrole dyes with good water solubility have been reported [Org.Lett.2008, 10, 4065-4067; J.Org .Chem.2008,73,1963-1970]
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Embodiment 1
[0032] Synthesis of 4,4-difluoro-1,3,5,7-tetramethyl-8-(3,4,5-tris(dodecyloxyether))fluoroboron dipyrrole fluorescent dye: 3,4 2.0 mmol of 5-tris(dodecyloxyether) benzaldehyde and 4.0 mmol of 2,4-dimethylpyrrole were mixed in 15 ml of anhydrous dichloromethane under nitrogen atmosphere, and then 0.016 ml of trifluoroacetic acid was added. After reacting for 4 hours, add 10 ml of anhydrous tetrahydrofuran dissolved in 0.454 g of dichlorodicyanobenzoquinone, and react for 1 hour. Finally, 4.0 ml of triethylamine was added, and the reaction was continued for 15 minutes, and then 31.6 mmol of boron trifluoride ether solution was added, and the reaction was continued for 4 hours. The reaction was quenched, the layers were separated, the solvent was removed from the organic layer, and the product was obtained by column chromatography. 1 H NMR: (400MHz, CDCl 3 ):6.47(s,2H),5.99(s,2H),3.96(qd,J=19.54,6.49Hz,6H,),2.55(s,6H),1.87-1.70(m,6H),1.53(s ,6H),1.49-1.39(m,6H),1.26(s,48H),0.8...
Embodiment 2
[0035] Under nitrogen atmosphere, 0.2 g of 4,4-bis-(3-dimethylamino-1-propyne)-1,3,5,7-tetramethyl-8-(3,4,5-tri (Lauryloxyether)) fluoroborate dipyrrole fluorescent dye and 0.1ml of methyl iodide were dissolved in 20ml of anhydrous ether, and refluxed for several hours until no solid precipitated. After the reaction, spin out the solvent, add a small amount of dichloromethane to dissolve the solid, and recrystallize in ether. A dark solid was obtained by suction filtration, and 0.2 g of product was obtained after vacuum drying. 1H NMR(400MHz, CDCl3):6.50(s,2H),6.01(s,2H),4.02(d,J=6.36Hz,2H),3.91(t,J=6.53Hz,4H),3.22(s, 4H),2.78(s,6H),2.30(s,12H),1.77(dd,J=14.22,7.01Hz,6H),1.52(s,6H),1.48-1.39(m,6H),1.25(s ,48H),0.88(dd,J=6.76,3.88Hz,9H).
[0036]
Embodiment 3
[0038] Under nitrogen atmosphere, 0.14 g of 4,4-bis-(3-dimethylamino-1-propyne)-1,3,5,7-tetramethyl-8-(4-methyl)fluoroboron The dipyrrole fluorescent dye and 0.1ml of iodomethane were refluxed in anhydrous ether for several hours until no solid precipitated out. Spin out the solvent, add a small amount of dichloromethane to dissolve, and recrystallize with ether. Suction filtration yielded a dark solid, which yielded 0.14 g of product after vacuum drying for ten hours. 1H NMR (400MHz, DMSO): 2.40(s,3H), 2.65(s,6H), 3.07(s,18H), 4.30(s,4H), 6.26(s,2H), 7.18(AB,sys,2H ,J=4Hz),7.37(AB,sys,2H,J=6.4Hz).
[0039]
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Abstract
The invention relates to a boron fluoride dipyrrole fluorescent dye containing hydrophilic groups and a preparation method thereof. The preparation method comprises the steps of introducing hydrophilic groups to a fluorine atom at 4 bit and fluorine atoms at 2 and 6 bits of BODIPY (boron dipyrromethene dyes) respectively to obtain relatively good water solubility of a whole molecule, wherein the hydrophilic groups are 3-dimethyl amino-1-propyne; enabling 2,4-dimethyl pyrrole to react with aldehyde or acyl chloride containing different substituent groups under catalysis of trifluoroacetic acid according to a molar ratio of 2:1, and then oxidizing by using DDQ (dichloro dicyano quinone) to obtain a basic BODIPY parent structure. The new synthetic method of a quaternary ammonium salt water-soluble BODIPY dye, disclosed by the invention, is simple in reaction condition and relatively high in yield. The BODIPY dye with 3-dimethyl amino-1-propyne groups has a relatively good aggregation property; the obvious aggregation process can be observed in the solution of water and dimethyl sulfoxide; moreover, the fluorescence spectrum of an aggregate has a sharp peak shape, and the strength of the aggregate is extremely high.
Description
technical field [0001] The invention relates to the technical field of dyes, in particular to a class of fluorobodipyrrole fluorescent dyes containing hydrophilic groups and a preparation method thereof. Background technique [0002] Fluoroboron dipyrromethene fluorescent dye (BODIPY) was first synthesized and reported in 1968 [Liebigs.Ann.Chem.1968,718,208-223]. This type of fluorescent dye has been widely studied by the scientific community because of its unique physical and chemical properties, such as: higher fluorescence quantum yield, narrower fluorescence spectrum half-width and good stability [Chem.Rev. 2007, 107, 4891-4932]. Niu[Org.Lett.2009,11,2049-2052] et al. reacted fluoroboron dipyrrole molecules with Grignard reagents, replaced fluorine atoms with dimethylaminopropynyl groups that can form quaternary ammonium salts, and then combined with 1 , 3-propane sultone reaction, obtained a new type of water-soluble sulfonate dyes. In addition, the research group us...
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