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Compound based on aggregation-induced emission and excited state proton transfer and preparation method and application thereof

A technology of aggregation-induced luminescence and proton transfer, which is used in material excitation analysis, chemical instruments and methods, luminescent materials, etc., and can solve the problems of short emission wavelength, low fluorescence quantum yield, and low sensitivity.

Inactive Publication Date: 2017-11-03
HAINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The currently developed fluorophores based on AIE and ESIPT mechanisms are still very limited, mainly salicylaldehydeazine (Journal of Materials Chemistry C, 2016, 4, 2909-2914; J. Mater. Chem. B, 2015, 3, 1590-1596), Chalcone derivatives (ACS applied materials & interfaces, 2014, 6, 17245-17254), hydroxyphenyl quinazolinone (Analytical Methods, 2017, 9, 1872-1875), etc. Although these compounds have been successfully developed, there are still some Defects, such as low sensitivity, low fluorescence quantum yield, or short emission wavelength

Method used

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  • Compound based on aggregation-induced emission and excited state proton transfer and preparation method and application thereof
  • Compound based on aggregation-induced emission and excited state proton transfer and preparation method and application thereof
  • Compound based on aggregation-induced emission and excited state proton transfer and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of compound I of the present invention

[0033] (1)

[0034]

[0035] Tetraphenylethylene hydroxyl derivatives, compound 1 (2.0 g, 5.8 mmol), MgCl 2 (1.7 g, 17.8 mmol) and paraformaldehyde (1.2 g, 40 mmol) were dissolved in anhydrous THF (40 mL), then triethylamine (3.2 mL, 23 mmol) was added, and the reaction mixture was refluxed overnight at 75°C . For post-treatment, the reaction was first quenched with 1 mol / L hydrochloric acid solution, then extracted with dichloromethane, and finally compound 2 was obtained as a yellow solid by column chromatography.

[0036] 1 H NMR (400 MHz, CDCl 3 ): δ 10.94 (s, 1H), 9.58 (s, 1H), 7.19 (s, 2H),7.18 – 7.09 (m, 9H), 7.05 (s, 6H), 6.73 (d, J = 8.2 Hz, 1H); 13 C NMR (101 MHz, CDCl 3 ): δ 196.90, 160.44, 143.65, 143.63, 143.33, 141.76, 140.44, 139.14,136.74, 135.95, 131.65, 131.57, 131.53, 128.36, 128.24, 128.05, 127.15,127.10, 126.94, 120.43, 117.26; HRMS (ESI): m / z [M-H] - calcd for C 27 h 20 o 2 ,375.1...

Embodiment 2

[0042] Using compound I as the parent compound, the fluorescent probe L obtained after modification is applied to biothiol imaging, as follows:

[0043]

[0044] Under anhydrous and oxygen-free conditions, triethylamine (21 μL, 0.15 mmol) was added to a solution of compound Ⅰ (50 mg, 0.11 mmol) in dichloromethane, stirred at -78°C for 10 min, and then 2,4- Dinitrobenzenesulfonyl chloride (38 mg, 0.15 mmol) was stirred at room temperature for 2 h, and finally purified to obtain probe L as a yellow solid.

[0045] 1 H NMR (400 MHz, CDCl 3 ): δ 8.20 (s, 1H), 7.81 (dd, J = 20.2, 7.6 Hz, 3H),7.72 (d, J = 7.5 Hz, 1H), 7.45 (d, J = 14.8 Hz, 2H), 7.34 (d, J = 6.9 Hz,1H), 7.21 (d, J = 17.1 Hz, 5H), 7.16 – 7.06 (m, 10H), 7.03 (s, 2H); 13 C NMR (101 MHz, CDCl 3 ): δ 162.47, 153.18, 150.00, 148.36, 144.86, 144.68, 143.65,143.20, 142.71, 138.66, 135.91, 135.10, 134.69, 134.28, 132.99, 131.68,131.65, 131.46, 128.47, 128.39, 128.12, 127.46, 127.38, 127.29 , 127.00, 126.70, 1...

Embodiment 3

[0047] We can derive a class of compounds with both AIE and ESIPT mechanisms and more applications, as follows:

[0048]

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a compound based on aggregation-induced emission (AIE) and excited state proton transfer (ESIPT) and a preparation method and application in biological detection. The compound has the structure shown in a formula (I), aldehyde group treatment is performed based on a tetraphenyl ethylene based derivative to obtain an intermediate, the intermediate is further condensed with 2-amino thiophenol under certain conditions to obtain a target compound. The compound I is a fluorescent material novel in structure and meanwhile having the two mechanisms of aggregation-induced emission (AIE) and excited state proton transfer (ESIPT), shows large Stokes shift (greater than 200 nm), does not produce fluorescence quenching in high concentration, and has the advantages of having good light stability and high solid-state fluorescence quantum yield (0.97) and the like. Based on the advantages, the compound is applied to imaging of biological mercaptan in cells.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a compound with an aggregation-induced emission (AIE) mechanism and an excited-state intramolecular proton transfer (ESIPT) mechanism, its preparation method and its application in biological imaging. Background technique [0002] A class of fluorescent materials developed in recent years has both mechanisms of aggregation-induced emission (AIE) and excited-state intramolecular proton transfer (ESIPT), which has opened up new avenues for biosensing and imaging applications and has triggered more and more The attention of scientific researchers (Analytical Chemistry, 2017, 89, 3162-3168; Materials Chemistry Frontiers, 2017, 1, 838-845). Compounds with AIE mechanism have strong fluorescence in aggregated state or solid state. By forming aggregated state or solid state, the interference of polar solvents or protic solvents can be avoided, which is conducive to the smooth p...

Claims

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Application Information

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IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06C09K2211/1007C09K2211/1037G01N21/643G01N2021/6432
Inventor 贾春满张岐陈清
Owner HAINAN UNIVERSITY
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