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Dithienyl ethylene-trinaphthalene diphenyl imide near-infrared-fluorescence molecular switch and preparation method thereof

A technology of terrylene imide and dithienylethylene, which is applied in the field of fluorescent probes, can solve the problems of poor photostability, slow photoresponse, and low fluorescence quantum yield, and achieve good fatigue resistance and enhanced Effect of speed and quenching efficiency, high fluorescence quantum yield

Active Publication Date: 2017-08-11
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the above defects or improvement needs of the prior art, the present invention provides a dithienylethylene-terrylene imide molecule and a preparation method thereof, and applies it to near-infrared fluorescent molecules, the purpose of which is to pass Four dithienylethylenes are non-conjugated with a single terrylene through an oxygen bridge to construct a highly efficient butterfly-shaped dithienylethylene-terrylene, in which the dithienyl Ethylene is a photochromic unit, which is used to control the emission and quenching of near-infrared fluorophores, and terrylene diphenylimide is a fluorophore, which is used to emit near-infrared fluorescence at 650nm to 800nm, thereby solving the problem of existing Technical near-infrared diarylethene fluorescent molecular switches have many obvious shortcomings, such as poor photostability, complex synthesis, low fluorescence quantum yield, and slow photoresponse technical problems

Method used

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  • Dithienyl ethylene-trinaphthalene diphenyl imide near-infrared-fluorescence molecular switch and preparation method thereof
  • Dithienyl ethylene-trinaphthalene diphenyl imide near-infrared-fluorescence molecular switch and preparation method thereof
  • Dithienyl ethylene-trinaphthalene diphenyl imide near-infrared-fluorescence molecular switch and preparation method thereof

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preparation example Construction

[0043] The preparation method of described four (R-dithienylethylene)-terrylene imide, comprises the steps:

[0044] (1) Compound A, compound B and sodium carbonate are uniformly dispersed in a 4:1 mixed solution of ethylene glycol dimethyl ether and water according to a molar ratio of 1:1:5, and under nitrogen protection, a catalyst dose of Pd (PPh 3 ) 4 , heated to 80-100 DEG C for 12-24 hours, after the completion of the reaction, separation and purification to obtain compound C, the molecular structures of A, B and C are shown in formula (A), formula (B) and formula (C);

[0045]

[0046] (2) The compound C, p-hydroxyphenylboronic acid and sodium carbonate are uniformly dispersed in a 4:1 mixed solution of ethylene glycol dimethyl ether and water according to a molar ratio of 1:1:5, and under nitrogen protection, add Catalyst dosage of Pd(PPh 3 ) 4 , heated to 80-100°C and reacted for 12-48 hours. After the reaction was completed, the compound D was obtained after s...

Embodiment 1

[0060] A near-infrared fluorescent molecular switch shown in formula (I), wherein the substituent R is R 1 for

[0061]

[0062] Its synthetic route is as follows image 3 Shown, preparation method comprises the steps:

[0063] (1) 1-(5-bromo-2-methylthiophen-3-yl)-2-[2-methyl-5-(4-octyloxyphenyl)thiophen-3-yl]perfluorocyclopentyl Synthesis of alkenes (compound C, structural formula shown in formula (C)).

[0064] Add 1,2-bis(5-bromo-2-methylthiophen-3-yl)perfluorocyclopentene (1.58g, 3mmol), 4-octyloxyphenylboronic acid (0.75 g, 3mmol), anhydrous sodium carbonate (1.59g, 15mmol), water (6ml) and ethylene glycol dimethyl ether (DME, 24ml) and stirred with a magnetic force, blowing nitrogen into the mixture for 30min to fully remove the solvent and the reaction system of oxygen. Then add the zero-valent palladium catalyst Pd(PPh 3 ) 4 (0.17g, 0.15mmol), immediately use a double-row tube to carefully evacuate nitrogen three times, so that the entire system is stric...

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Abstract

The invention discloses a dithienyl ethylene-trinaphthalene diphenyl imide near-infrared-fluorescence molecular switch, and a compounding method and application thereof. Multiple dithienyl ethylene are conjugated with single trinaphthalene diphenyl imide through oxygen bridge bonds, so that the defect that switching of a fluorophore cannot be controlled completely by the single trinaphthalene diphenyl imide can be overcome, and fluorescence switching speed and quenching efficiency can be enhanced effectively. The efficient butterfly dithienyl ethylene-trinaphthalene diphenyl imide is created, wherein the dithienyl ethylene is photochromic units and used for controlling illuminating and quenching of near infrared fluorescence clusters, and the trinaphthalene diphenyl imide is a fluorescence cluster used for emitting 650-800nm near infrared fluorescence, so that the obvious defects, such as low light stability, high compounding complexity, low fluorescence quantum yield and slow photoresponse, of near infrared diarylethene fluorescent molecular switches in the prior art are overcome.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and more specifically relates to a dual-wavelength controlled near-infrared fluorescent molecular switch butterfly dithienylethylene-terrylene imide, its preparation method and application. Background technique [0002] Photochromic materials refer to a class of materials that can reversibly change their optical properties and undergo color changes after being excited by light sources of different wavelengths. Diarylethenes are one of the most promising photochromic compounds due to their bistability and good fatigue resistance. The fluorescent molecular switch constructed of diarylethene and fluorescent group can regulate the fluorescence emission behavior of the fluorescent group through the photochromic effect of diarylethene, so as to realize the optical switch of molecular fluorescence. It is used in optical storage, Applications in the fields of optical switches, all-optical tra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06G01N21/64
Inventor 朱明强谢诺华李冲
Owner HUAZHONG UNIV OF SCI & TECH
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