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A near-infrared reactive two-photon fluorescent probe and its preparation method and application

A two-photon fluorescence and near-infrared technology, which is applied in the field of fluorescent probes, can solve the problems of limited application range and achieve high sensitivity, good biocompatibility, and wide application

Active Publication Date: 2019-05-28
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the reactive rhodamine fluorescent probes in the prior art only emit linear fluorescence without two-photon fluorescence, and most of the linear fluorescence emission wavelengths are less than 670nm, which greatly limits its application range

Method used

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  • A near-infrared reactive two-photon fluorescent probe and its preparation method and application
  • A near-infrared reactive two-photon fluorescent probe and its preparation method and application
  • A near-infrared reactive two-photon fluorescent probe and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0018] (1) The preparation method of fluorescent molecule CRPM is:

[0019] Under nitrogen protection, 1,3,3-trimethyl-2-methyleneindoline-rhodamine lactide (0.50 g, 0.87 mmol) was dissolved in 30 mL of anhydrous acetonitrile, and 4-morpholinyl was added. -1,8-Naphthalimide-phenyl isothiocyanate (0.36 g, 0.87 mmol), magnetically stirred, refluxed for 24 h, and the temperature was controlled at 80 °C. After the reaction was completed, CRPM was obtained by extraction, drying and purification by column chromatography with a yield of 45%.

[0020] The synthetic route of compound CRPM is as follows:

[0021]

[0022] Among them, 1,3,3-trimethyl-2-methyleneindoline-rhodamine hydrazide was prepared according to literature methods (JunyingXie, Chunyan Li, Yongfei Li, JunjieFei, Fen Xu, Juanou Yang, and Juan Liu.Near -InfraredFluorescent Probe with High Quantum Yield and Its Application in the Selective Detection of Glutathione in Living Cells and Tissues. Analytical Chemistry, 20...

Embodiment 2

[0030] The preparation method of fluorescent molecule CRPM is:

[0031] Under nitrogen protection, 1,3,3-trimethyl-2-methyleneindoline-rhodamine lactide (0.20 g, 0.35 mmol) was dissolved in 20 mL of anhydrous acetonitrile, and 4-morpholinyl was added. -1,8-Naphthalimide-phenylisothiocyanate (0.15 g, 0.35 mmol) was refluxed under magnetic stirring for 12 h, and the temperature was controlled at 80 °C. After the reaction was completed, CRPM was obtained by extraction, drying and purification by column chromatography with a yield of 40%.

Embodiment 3

[0033] The preparation method of fluorescent molecule CRPM is:

[0034] Under nitrogen protection, 1,3,3-trimethyl-2-methyleneindoline-rhodamine lactide (0.20 g, 0.35 mmol) was dissolved in 20 mL of anhydrous acetonitrile, and 4-morpholinyl was added. -1,8-Naphthalimide-phenylisothiocyanate (0.15 g, 0.35 mmol) was refluxed under magnetic stirring for 24 h, and the temperature was controlled at 75 °C. After the reaction was completed, CRPM was obtained by extraction, drying and purification by column chromatography with a yield of 45%.

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Abstract

The invention provides a near-infrared reactive type two-photon fluorescence probe. The near-infrared reactive type two-photon fluorescence probe is a fluorescence molecule which is prepared by the reaction of 1,3,3-trimethyl-2-methylene indoline-rhodamine hydrazine and 4-morpholinyl-1,8-naphthalimides-phenyl isothiocyanate. The invention also provides a preparation method and application of the near-infrared reactive type two-photon fluorescence probe. According to the near-infrared reactive type two-photon fluorescence probe, red fluorescence in near-infrared band is transmitted, the fluorescence performance of the red fluorescence in the near-infrared band can be sensitively adjusted and controlled through mercury ion induced desulfuration-cyclization reaction of amidothiourea, ring-opening reaction of 1,3,3-trimethyl-2-methylene indoline-rhodamine lactam, and other multi-step cascade reactions, so that the sensitivity, the selectivity and the biocompatibility are high; the near-infrared reactive type two-photon fluorescence probe can be widely applied to the fields of near-infrared two-photon fluorescence imaging, two-photon fluorescence sensors, biofluorescence analysis, fluorescence labelling, environment monitoring and the like.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a near-infrared reactive two-photon fluorescent probe and a preparation method and application thereof. Background technique [0002] Reactive fluorescent probes directly change the structure of probe molecules through chemical reactions, causing significant changes in their spectral signals, thereby realizing optical sensing and target recognition. Rhodamine is an ideal material for preparing reactive fluorescent probes. In 2014, Wang et al. reported a rhodamine-naphthalimide iron ion fluorescent probe (Cuicui Wang, Di Zhang, Xiaoyan Huang, Peigang Ding, Zhenji Wang, Yufen Zhao, Yong Ye. A fluorescenceratiometric chemosensor for Fe 3+ based on TBET and its application in living cells. Dyes and Pigments, Talanta, 128, 2014, 69-74); in 2015, Zhang et al. reported a pH fluorescent probe for rhodamine-aminomorpholine naphthalene (Xiaofan Zhang, Tao Zhang, ShiliShen, Jun...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1033C09K2211/1088G01N21/6428G01N21/6486
Inventor 钱鹰姚善昆
Owner SOUTHEAST UNIV
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