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Yellow light excited fluorescent dye as well as preparation method and application thereof

A technology for exciting fluorescence and yellow light, applied in luminescent materials, azo dyes, organic dyes, etc., can solve the problem of difficulty in the synthesis of fluorescent dyes excited by yellow light, reduce the interference of self-absorption and self-fluorescence, and enhance the fluorescence of organic molecules , the effect of simple synthesis process

Inactive Publication Date: 2018-06-08
SUZHOU BAIYUAN GENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, the technical problem to be solved in the present invention is to overcome the difficulty in the synthesis of yellow-light-excited fluorescent dyes in the prior art, thereby providing a yellow-light-excited fluorescent dye with a novel structure, simple preparation method and excellent performance

Method used

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  • Yellow light excited fluorescent dye as well as preparation method and application thereof
  • Yellow light excited fluorescent dye as well as preparation method and application thereof
  • Yellow light excited fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation method of the yellow light-excited fluorescent dye (II) provided in this embodiment:

[0036] Has formula (II) structure:

[0037]

[0038] Its preparation method is as follows:

[0039]

[0040] (1) Preparation of intermediate 1-II

[0041] Weigh 29.4g (0.1mol) of 4,7-dibromobenzo[c][1,2,5]thiadiazole, 1,2-bis(1,3,2-dioxaborolane-2- Base) 48.5g (0.25mol) of acetylene and 2.3g (0.002mol) of tetrakis (triphenylphosphine) palladium were added to a 1000ml three-necked flask, vacuumed and fed with nitrogen for 5min, 600ml of toluene was added, and 5.3g (0.05mol) of sodium carbonate was added. mol), heating to reflux, TLC detection of 4,7-dibromobenzo[c][1,2,5]thiadiazole, the reaction was completed, cooled to 20°C, extracted with dichloromethane, 100ml each time, and collected the organic layer , spin-dried, and passed through a column (MeOH:DCM=1:10) to obtain a solid, namely Intermediate 1-II.

[0042] (2) Preparation of intermediate 2-II

[004...

Embodiment 2

[0052] The preparation method of the yellow light-excited fluorescent dye (III) provided in this embodiment:

[0053] Has the structure of formula (III):

[0054]

[0055] Its preparation method is as follows:

[0056]

[0057] (1) Preparation of intermediate 1-III

[0058] Weigh 141.9 g (0.5 mol) of 4,7-dibromobenzo[c][1,2,5]thiadiazole, 1,2-bis(1,3,2-dioxaborolane-2- Base) 291.1g (1.5mol) of acetylene and 1.7g (0.015mol) of tetrakis (triphenylphosphine) palladium were added to a 10000ml three-neck flask, vacuumed and fed with nitrogen for 5min, 5000ml of toluene was added, and 26.5g (0.25mol) of sodium carbonate was added mol), heating to reflux, TLC detection of 4,7-dibromobenzo[c][1,2,5]thiadiazole, the reaction was completed, cooled to 20°C, extracted with dichloromethane, 1000ml each time, and collected the organic layer , spin-dried, and passed through a column (MeOH:DCM=1:10) to obtain a solid, namely Intermediate 1-III.

[0059] (2) Preparation of Intermedia...

Embodiment 3

[0069] The preparation method of the yellow light-excited fluorescent dye (IV) provided in this embodiment:

[0070] Has formula (IV) structure:

[0071]

[0072] Its preparation method is as follows:

[0073]

[0074] (1) Preparation of Intermediate 1-IV

[0075] Weigh 4,7-dibromobenzo[c][1,2,5]thiadiazole 116.7g (0.4mol), 1,2-bis(1,3,2-dioxaborolane-2- Base) 232.9g (1.2mol) of acetylene and 13.9g (0.012mol) of tetrakis (triphenylphosphine) palladium were added to a 5000ml three-necked flask, vacuumed and fed with nitrogen for 5min, 2400ml of toluene was added, and 21.2g (0.2mol) of sodium carbonate was added. mol), heating to reflux, TLC detection of 4,7-dibromobenzo[c][1,2,5]thiadiazole, the reaction was completed, cooled to 20°C, extracted with dichloromethane, 500ml each time, and collected the organic layer , spin-dried, and passed through a column (MeOH:DCM=1:10) to obtain a solid, namely Intermediate 1-IV.

[0076] (2) Preparation of intermediate 2-VI

[007...

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Abstract

The invention relates to the field of photo-functional materials, in particular to a yellow light excited fluorescent dye. The yellow light excited fluorescent dye has a structure shown as the formula(I) in the description. The yellow light excited fluorescent dye has quite wide excitation spectrum, is good in photostability and high in sensitivity, can be used in different application fields such as cell imaging, fluorescence probes, laser dyes, fluorescence sensors and the like, and shows good practicability. According to the preparation method, raw material cost is low, no pollution is produced, the process is simple, and yield is high; the prepared fluorescent dye is novel in structure, good in performance and suitable for being widely applied to the fields of biology, environment andthe like.

Description

technical field [0001] The invention relates to the field of optical functional materials, in particular to a yellow light-excited fluorescent dye and its preparation method and application. Background technique [0002] Fluorescent dyes generally refer to substances that absorb light waves of a certain wavelength and emit light waves of another wavelength greater than the absorbed light. Most of them are compounds containing benzene rings or heterocycles with conjugated double bonds. Each molecule has a series of strict discrete energy levels. Most of the material molecules are in the "ground state" at room temperature. When these substances absorb light energy under the irradiation of light, they enter a new state, called the "excited state", in the " Excited state" molecular weight is unstable, it can pass 10 -9 ~10 -7 In a very short period of time, the emitted light quantum returns to the ground state, and this process emits fluorescence. Since the 20th century, flu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09B57/00G01N21/64H01L51/00H10K99/00
CPCG01N21/6428G01N21/6486C09K11/06C09B57/00C09K2211/1011C09K2211/1007C09K2211/1051C09K2211/1092H10K99/00H10K85/655H10K85/657
Inventor 车团结徐进章赵芳
Owner SUZHOU BAIYUAN GENT CO LTD
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