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Organosilicon group-modified fluorine-boron dipyrrole fluorochrome and preparation method and application thereof

A fluoroborondipyrrole and a fluoroborondipyrrole technology are applied in the field of organosilicon group-modified fluoroborondipyrrole fluorescent dyes and the preparation thereof, which can solve the problems of no report on the organosilicon group-modified system, and achieve easy industrialization. Production, high molar extinction coefficient, low equipment requirements

Inactive Publication Date: 2017-03-01
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, all studies are based on carbon chemical modification systems, and there is no report on organosilicon group modification systems.

Method used

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  • Organosilicon group-modified fluorine-boron dipyrrole fluorochrome and preparation method and application thereof
  • Organosilicon group-modified fluorine-boron dipyrrole fluorochrome and preparation method and application thereof
  • Organosilicon group-modified fluorine-boron dipyrrole fluorochrome and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a (10ml) schlenk reaction tube, add monoiodoBODIPY (100mg, 0.230mmol), triphenylsilane (299mg, 1.15mmol), ditri-tert-butylphosphine palladium (5.88mg, 0.012mmol) under nitrogen Under protection, 2 ml of toluene and triethylamine (0.037 ml, 0.345 mmol) were added to adjust the alkaline environment, and stirred at room temperature for 1 day. Separation with a chromatographic column (EA:HEX=1:19) can give the product as a bright yellow solid, the single crystal diffraction pattern is shown in (I-A), and the structural formula is as shown in (I-1) Organosilicon group modified fluorine Borodipyrrole Fluorescent Dye 1.

[0023]

[0024] 1H NMR (400MHz, CDCl3) δ7.93(s, 1H), 7.88(s, 1H), 7.49(dd, J=7.9, 1.4Hz, 6H), 7.44-7.40(m, 3H), 7.35(dd, J=11.2, 4.4Hz, 6H), 6.93(s, 3H), 6.70(d, J=4.1Hz, 1H), 6.49(d, J=3.0Hz, 1H), 2.34(s, 3H), 2.12( s, 6H).

[0025] HR-MS: Calcd. For C 36 h 31 BF 2 N 2 NaSi[M+Na] + 591.2216. Found 591.2212

[0026] The synthetic reaction equat...

Embodiment 2

[0029] In one (10ml) schlenk reaction tube, add 2,6-diiodoBODIPY (100mg, 0.178mmol), triphenylsilane (463mg, 1.78mmol), ditri-tert-butylphosphine palladium (9.20mg, 0.0178mmol ), under nitrogen protection, 2 ml of toluene and diisopropylethylamine (0.058 ml, 0.534 mmol) were added to adjust to an alkaline environment, and stirred at room temperature for 2 days. Separation with a chromatographic column (EA:HEX=3:97) can give the product as a bright yellow solid, the single crystal diffraction pattern is shown in (I-B), and the structural formula is shown in (I-2) Organosilicon group modified fluorine Boron dipyrrole fluorescent dye 2.

[0030]

[0031] 1 H NMR (400MHz, CDCl 3 )δ: 7.94(s, 1H), 7.82(s, 1H), 7.49-7.47(m, 6H), 7.45-7.41(m, 3H), 7.38-7.34(m, 6H), 7.01(s, 1H) , 6.93(s, 2H), 6.78(s, 1H), 2.33(s, 3H), 2.11(s, 6H).

[0032] HR-MS: Calcd. For C 54 h 45 BF 2 N 2 NaSi 2 [M+Na] + 849.3084. Found 849.3080

[0033] The synthetic reaction equation is as follows: ...

Embodiment 3

[0036] In a (10ml) schlenk reaction tube, add monoiodo BODIPY (100mg, 0.230mmol), triethylsilane (0.043ml, 0.276mmol), ditri-tert-butylphosphine palladium (7.84mg, 0.016mmol), in Under nitrogen protection, 2 ml of dichloromethane and triethylamine (0.037 ml, 0.345 mmol) were added to adjust the alkaline environment, and stirred at room temperature for 2 days. Separation with a chromatographic column (EA:HEX=1:19) can give organosilicon group-modified fluorobodipyrrole fluorescent dye 3 with the structural formula (I-3).

[0037] The synthetic reaction equation is as follows:

[0038]

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Abstract

The invention relates to the technical field of organic chemical industry and fine chemical engineering, and provides an organosilicon group-modified fluorine-boron dipyrrole fluorochrome and a preparation method and an application thereof, which solve all problems of a modification system based on carbon chemistry. Under inert gas protection, iodo BODIPY and silane-containing hydrogen are taken as the raw materials, under alkaline condition, the raw materials are subjected to a catalytic reaction for 24-72 hours in a solvent at room temperature, and the material is separated through silica-gel column chromatography to prepare the organosilicon group-modified fluorine-boron dipyrrole fluorochrome. The organosilicon group-modified fluorine-boron dipyrrole fluorochrome has excellent spectrum properties such as high molar extinction coefficient and high fluorescence quantum yield, can greatly increase the light stability, and is the ideal light functional material.

Description

technical field [0001] The invention relates to the technical fields of organic chemical industry and fine chemical industry, in particular to an organosilicon group-modified fluoroboron dipyrrole fluorescent dye and a preparation method and application thereof. Background technique [0002] Fluoroboron dipyrrole molecule (BODIPY) is a kind of fluorescent compound with excellent photophysical and chemical properties, which was developed in the past 20 years and has been widely valued. Structurally, as shown in (A), the pyrrole rings are fixed on a plane by boron bridges and methine bridges, and have a rigid planar structure. [0003] [0004] It has the following advantages: (1) Since the parent structure of BODIPY dyes is generally not directly connected with acid-base-sensitive amino groups, hydroxyl groups, etc., BODIPY dyes are generally not sensitive to acid-base. (2) The fluorescence quantum yield of BODIPY dyes is generally relatively high, and some even have a fl...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B57/00C07F7/10
CPCC09K11/06C07F7/0827C09B57/00C09K2211/1029C09K2211/1055
Inventor 卢华王思斯李志芳
Owner HANGZHOU NORMAL UNIVERSITY
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