Pyrrole hydrazone hydrazine difluoroboron hyperfluorescence dye and preparation method thereof

A technology of pyrrole hydrazone and fluorescent dyes, which is applied in the fields of organic synthesis and fluorescent dye preparation, and can solve the problems of limited molecular types of strong fluorescent dyes with molar extinction coefficient

Active Publication Date: 2018-09-14
ANHUI NORMAL UNIV
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  • Description
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Problems solved by technology

However, at present, the types of strong fluorescent dye molecules that are really suitable for industrial applications, which have many advantages such as large molar extinction coefficient, fluorescence quantum efficiency, good photostability, and can be modified and derivatized to control the absorption and emission bands, are still very limited.

Method used

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  • Pyrrole hydrazone hydrazine difluoroboron hyperfluorescence dye and preparation method thereof
  • Pyrrole hydrazone hydrazine difluoroboron hyperfluorescence dye and preparation method thereof
  • Pyrrole hydrazone hydrazine difluoroboron hyperfluorescence dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0047] Synthesis of pyrrole hydrazone difluoroboron strong fluorescent dye 1a:

[0048]

[0049] Dissolve 2-pyrrolealdehyde (190mg, 2mmol) and 2-hydrazinobenzothiazole (348mg, 2.1mmol) in 2-dichloroethane (60ml), add p-toluenesulfonic acid (87mg, 0.05mmol) . The reaction mixture was heated to reflux for 6 h, followed by TLC spot plate. When the 2-pyrrole aldehyde derivative disappears on the silica gel plate, that is, when the reaction is complete, add 2-10 mL of N,N-diisopropylethylamine into the reaction system. After the reaction mixture was stirred for 10 min, boron trifluoride ether (3-20 ml) was added, and the reaction system was stirred and refluxed for 2 h. After cooling to room temperature, the reaction mixture was transferred to a separatory funnel, and dichloromethane and water were added. The organic phase was separated, the corresponding aqueous phase was extracted several times with dichloromethane, and the organic layers were combined. Wash with water, dr...

Embodiment example 2

[0055] Synthesis of pyrrole hydrazone difluoroboron strong fluorescent dye 1b:

[0056]

[0057] The synthesis operation of 1b is the same as that of 1a in Example 1, the only difference is that pyrrolealdehyde is changed to the same equivalent of 2,4-dimethylpyrrolealdehyde (246mg, 2mmol), and the yield of preparation 1b is 23% (168 mg). 1 H NMR (300MHz, CDCl 3 ):δ=7.70-7.62(m,3H),7.50(t,J=7.5Hz,1H),7.34(t,J=7.5Hz,1H),6.18(s,1H),2.50(s,3H) ,2.32(s,3H). 13 C NMR (75MHz, CDCl 3 ): δ=149.7, 138.9, 137.5, 130.8, 128.3, 128.1, 124.9, 123.1, 118.2, 115.1, 14.1, 11.0. 19 F NMR (470MHz, CDCl 3 ):δ=-144.4(d, J=27.3Hz, 1F), -144.5(d, J=26.8Hz, 1F), -146.9(d, J=18.3Hz, 1F), -147.0(d, J= 18.8Hz,1F).HRMS(APCI)Calcd.For C 14 h 12 B 2 f 3 N 4 S[M-F] + :347.0921, found 347.0948.

[0058] And the spectral properties of 1b in different solvents were detected, and the test results are shown in Table 2:

[0059] Table 2

[0060]

[0061] In Table 2: λabsmax is the maximum ab...

Embodiment example 3

[0063] Synthesis of pyrrole hydrazone difluoroboron strong fluorescent dye 1c:

[0064]

[0065] The synthesis operation of 1c is the same as that of 1a in Example 1, the only difference is that pyrrolealdehyde is changed to the same equivalent of 2,4-dimethyl-3-ethylpyrrolealdehyde (304mg, 2mmol) to prepare 1c The yield was 28% (220 mg). 1 HNMR (300MHz, CDCl 3 ):δ=7.69-7.60(m,3H),7.48(t,J=7.5Hz,1H),7.32(t,J=7.5Hz,1H),2.46-2.41(m,5H),2.24(s, 3H), 1.08(t, J=7.5Hz, 3H). 13 C NMR (75MHz, CDCl 3 ): δ=148.3, 137.5, 135.6, 131.3, 130.1, 128.3, 128.0, 124.7, 123.0, 122.3, 115.0, 17.2, 14.7, 12.1, 9.2. 19 F NMR (470MHz, CDCl 3 ):δ=-144.2(d, J=26.8Hz, 1F), -144.3(d, J=26.3Hz, 1F), -146.9(d, J=17.4Hz, 1F), -147.0(d, J= 18.8Hz,1F).HRMS(APCI)Calcd.For C 16 h 16 B 2 f 3 N 4 S[M-F] + :375.1234, found 375.1235.

[0066] And the spectral properties of 1c in different solvents were detected, and the test results are shown in Table 3:

[0067] table 3

[0068]

[0069] Tabl...

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Abstract

The invention discloses a pyrrole hydrazone hydrazine difluoroboron hyperfluorescence dye and a preparation method thereof. The structure of the pyrrole hydrazone hydrazine difluoroboron hyperfluorescence dye is expressed as a general formula (1) which is as shown in the description, wherein R1, R2 and R3 are H or C1-C6 straight-chain or branched-chain alkyl; R5 is H, Cl, a thiophene group, a furan group, a benzene ring group, OR9, NR9R10 or SR9; R4, R6, R7 and R8 are H, C1-C6 straight-chain or branched-chain alkyl and C1-C6 straight-chain or branched-chain naphthene groups independently and separately; R9 and R10 are H, naphthyl, thienyl, C1-C6 straight-chain or branched-chain alkyl or C1-C6 straight-chain or branched-chain naphthene groups independently and separately. The pyrrole hydrazone hydrazine difluoroboron hyperfluorescence dye has the advantages of large molecular plane, high molar light absorption coefficient, high fluorescence quantum yield and highlight stability; meanwhile, the preparation method adopts a one-pot preparation process; and the method is simple. (The formula is shown in the description.).

Description

technical field [0001] The invention relates to the field of organic synthesis and preparation of fluorescent dyes, in particular to a pyrrole hydrazone difluoroboron strong fluorescent dye and a preparation method thereof. Background technique [0002] High-efficiency fluorescent dyes with excellent photoelectric properties such as high photochemical stability, high molar absorption coefficient, and tunable properties have been widely used in many fields such as bioimaging, sensing therapy, and organic light-emitting diodes. However, there are currently very limited types of strong fluorescent dye molecules that are truly suitable for industrial applications, with many advantages such as large molar extinction coefficient, fluorescence quantum efficiency, good photostability, and the ability to modify and derivatize the absorption and emission bands. Therefore, it is of great significance to design and develop new fluorescent dye frameworks with practical value and a series...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09B26/02C09K11/06
CPCC07F5/022C09B26/02C09K11/06C09K2211/107
Inventor 郝二宏于长江张年荣焦莉娟
Owner ANHUI NORMAL UNIV
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