Asymmetric naphthalene ring fused boron dipyrromethene fluorescent dye and preparation method thereof

A technology of naphthalene ring fused fluoroboron dipyrrole and fluoroboron dipyrrole, which is applied in the field of asymmetric naphthalene ring fused fluoroboron dipyrrole fluorescent dyes and its preparation, which can solve the problems of cumbersome synthesis methods and achieve simple preparation methods , excellent spectral properties, the effect of high molar extinction coefficient

Active Publication Date: 2017-07-14
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is: in order to solve the comparatively loaded down with trivial details of reported fused BODIPY synthesis method at present, the obtained product is based on the problem of symmetrical structure, proposes a kind of asymmetric naphthalene ring fused fluoroborate dipyrrole fluorescent dye and its preparation method, The synthesis method is simple, the separation is convenient, and the yield is high; and it has excellent spectral properties such as high molar extinction coefficient and strong fluorescence emission, which makes it high in photostability and can be further modified into molecular probes

Method used

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  • Asymmetric naphthalene ring fused boron dipyrromethene fluorescent dye and preparation method thereof
  • Asymmetric naphthalene ring fused boron dipyrromethene fluorescent dye and preparation method thereof
  • Asymmetric naphthalene ring fused boron dipyrromethene fluorescent dye and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a 50ml Schlenk reaction flask, add monoiodo BODIPY (50mg, 0.11mmol), 2-formylphenylboronic acid (25mg, 0.165mmol), tetrakistriphenylphosphine palladium (13mg, 0.011mmol), 20ml tetrahydrofuran, TBAB (35mg, 0.11mmol), 3mL 2M Na 2 CO 3 aqueous solution. Nitrogen was blown for 20 minutes, and the reaction was stirred at 80°C for 6 hours. Separation with a chromatographic column (DCM:PE=35:65) gave 17.7 mg of a purple-black solid product with a yield of 39%. The product whose structural formula is shown in (I-1) is an asymmetric naphthalene ring-fused fluorobodipyrrole fluorescent dye. 1 H NMR (400MHz, CDCl 3 )δ=8.22(d,1H),7.88(d,1H),7.80(d,1H),7.69(d,1H),7.57–7.56(m,3H),7.48(t,1H),7.41–7.37 (m,3H),6.16(s,1H),2.69(s,3H),2.01(s,3H),1.45(s,3H)ppm.MALDI-TOF-MS:calcd for[C 26 h 21 BF 2 N 2 ] + :410.18; found: 410.57[M] + ,391.52[M-F] + .

[0024] The synthetic reaction equation is as follows:

[0025]

[0026]

Embodiment 2

[0028] In a 50ml Schlenk reaction flask, add monoiodo BODIPY (50mg, 0.11mmol), 5-fluoro-2-formylphenylboronic acid (28mg, 0.165mmol), tetrakistriphenylphosphine palladium (13mg, 0.011mmol), 20ml THF, TBAB (35mg, 0.11mmol), 3mL 2M Na 2 CO 3 aqueous solution. Nitrogen was blown for 20 minutes, and the reaction was stirred at 80°C for 6 hours. Separation with a chromatographic column (DCM:PE=35:65) can obtain 21 mg of a purple-black solid product with a yield of 45%. The product of the structural formula (I-2) is an asymmetric naphthalene ring-fused fluorobodipyrrole fluorescent dye.

[0029] 1 H NMR (400MHz, CDCl 3 )δ=7.88-7.77(m,3H),7.67(d,1H),7.59–7.56(m,3H),7.41-7.38(m,2H),7.16-7.11(m,1H),6.18(s, 1H), 2.70(s,3H), 1.97(s,3H), 1.46(s,3H)ppm.

[0030] MALDI-TOF-MS: calcd for [C 26 h 20 BF 3 N 2 ] + :428.17; found: 428.47[M] + ,409.58[M-F] + .

[0031] The synthetic reaction equation is as follows:

[0032]

Embodiment 3

[0034] In a 50ml Schlenk reaction flask, add monoiodo BODIPY (50mg, 0.11mmol), 3-fluoro-2-formylphenylboronic acid (28mg, 0.165mmol), tetrakistriphenylphosphine palladium (13mg, 0.011mmol), 20ml THF, TBAB (35mg, 0.11mmol), 3mL 2M Na 2 CO 3 aqueous solution. Nitrogen was blown for 20 minutes, and the reaction was stirred at 80°C for 6 hours. Separation with a chromatographic column (DCM:PE=35:65) gave 10 mg of a purple-black solid product with a yield of 21%. The product of the structural formula (I-3) is an asymmetric naphthalene ring-fused fluorobodipyrrole fluorescent dye.

[0035] 1 H NMR (400MHz, CDCl 3)δ=8.03-8.01(m,3H),7.95(d,1H),7.72–7.67(m,1H),7.58(t,3H),7.42-7.37(m,2H),7.08(t,1H) ,6.19(s,1H),2.71(s,3H),1.99(s,3H),1.46(s,3H)ppm.

[0036] MALDI-TOF-MS: calcd for [C 26 h 20 BF 3 N 2 ] + :428.17; found: 428.34[M] + ,409.25[M-F] + .

[0037] The synthetic reaction equation is as follows:

[0038]

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Abstract

The invention belongs to the technical fields of fine chemical industry and organic synthesis, and concretely relates to an asymmetric naphthalene ring fused boron dipyrromethene fluorescent dye and a preparation method thereof. The asymmetric naphthalene ring fused boron dipyrromethene fluorescent dye has a structure represented by formula (I) shown in the description; and in the formula (I), Ar is selected from a phenyl group, a substituted phenyl group, a thienyl group, a substituted thienyl group, a furyl group and a substituted furyl group, and R is selected from a methyl group, a methoxy group and a fluoro group. The asymmetric naphthalene ring fused boron dipyrromethene fluorescent dye has the advantages of simple synthesis method, convenience in separation, and high yield, also has excellent spectral properties, such as high molar extinction coefficient and strong fluorescence emission, in order to realize high light stability, and can be further modified to form a molecular probe.

Description

technical field [0001] The invention relates to the technical fields of fine chemical industry and organic synthesis, in particular to an asymmetric naphthalene ring-fused fluoroborate dipyrrole fluorescent dye and a preparation method thereof. Background technique [0002] Fluoroboron dipyrrole (BODIPY) dyes are a class of fluorescent compounds with excellent photophysical and chemical properties, which were developed in the past two decades and have been widely valued. Its core structure and numbering system are shown in the following formula (A), and the two pyrrole rings are fixed in a rigid plane through a boron bridge bond and a methine bridge bond. This type of dye has good photothermal stability, large molar extinction coefficient (usually greater than 80000cm -1 m -1 ), strong modifiability, narrow spectral half-peak width, high fluorescence quantum yield, and insensitivity to environmental pH, etc., are widely used in biological labeling, organelle fluorescence i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00
CPCC07F5/022C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055
Inventor 周志宽周建平袁爱华
Owner JIANGSU UNIV OF SCI & TECH
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