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A kind of 2-pyridine vinyl naphthalimide fluorescent dendrimer and its preparation method and application

A pyridinevinylnaphthalimide and dendrimer technology, which is applied in the field of 2-pyridinevinylnaphthalimide fluorescent dendrimer and its preparation, and can solve the problems of aggregated fluorescence quenching, unfavorable fluorescence emission and the like

Inactive Publication Date: 2016-08-03
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the naphthalimide derivatives reported in the literature have good fluorescence properties in dilute solutions, but in the aggregated state due to intermolecular interactions that lead to non-radiative energy conversion or the formation of species that are not conducive to fluorescence emission, resulting in aggregation fluorescence quenching phenomenon

Method used

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  • A kind of 2-pyridine vinyl naphthalimide fluorescent dendrimer and its preparation method and application
  • A kind of 2-pyridine vinyl naphthalimide fluorescent dendrimer and its preparation method and application
  • A kind of 2-pyridine vinyl naphthalimide fluorescent dendrimer and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0030] Preparation of Fluorescent Dendrimer PAMAM-VPN from 2-pyridylvinylnaphthimide

[0031] Under the protection of nitrogen, in 30 mL methanol solution dissolved in VPN (0.51 g, 1.70 mmol), PAMAM (0.20 g, 0.39 mmol) in 20 mL methanol solution was slowly added dropwise, and the reaction was refluxed and stirred at 60 °C for 24 h. Distillation under reduced pressure, purification by column chromatography, recrystallization to obtain PAMAM-VPN, a fluorescent dendrimer of 2-pyridylvinylnaphthalimide, with a melting point of 232-234° C. and a yield of 45%.

[0032] The synthetic route is as follows:

[0033]

[0034] Analysis of the resulting fluorescent dendrimer PAMAM-VPN

[0035] H NMR spectrum 1 HNMR (CDCl 3 ,300MHz) δ: 8.68~8.58(m,4H), 8.45~8.30(m,4H), 8.26(d,J=6.0Hz,4H), 8.22(d,J=9.0Hz,4H), 8.16(d ,J=6.0Hz,4H), 7.76~7.68(m,8H), 7.61~7.53(m,4H), 7.49~7.43(m,4H), 7.37(d,J=6.0Hz,4H), 7.24~ 7.22(m,4H), 7.18(d,J=15.0Hz,2H), 7.07(d,J=12.0Hz,2H), 4.18~4.22(m,8H), 3.64~3.5...

Embodiment 2

[0041] Aggregation-induced luminescent properties of PAMAM-VPN

[0042] figure 1 is the solid-state fluorescence spectrum of PAMAM-VPN. The solid powder of PAMAM-VPN in the dark room emits bright yellow fluorescence under ultraviolet light, and its maximum fluorescence emission wavelength in solid state is 533nm. PAMAM-VPN is soluble in water, the maximum UV-visible absorption wavelength in pure water is 366nm, the maximum fluorescence emission peak is at 494nm, and the fluorescence quantum yield is 4.42%. In tetrahydrofuran, the ultraviolet-visible absorption peak of PAMAM-VPN is 363nm, the maximum fluorescence emission peak is 450nm, and the fluorescence quantum yield is 10.35%. figure 2 It is the change trend diagram of fluorescence intensity and fluorescence quantum yield of PAMAM-VPN in water / tetrahydrofuran mixed solutions with different volume ratios with water content. It shows that PAMAM-VPN has aggregation-induced luminescent properties, and can be used as aggreg...

Embodiment 3

[0044] Sensitive response of PAMAM-VPN to pH

[0045] image 3 It is the change trend graph of the fluorescence intensity of PAMAM-VPN at different pH. The fluorescence intensity of PAMAM-VPN decreased obviously with the gradual increase of pH value. It shows that PAMAM-VPN can be used as a sensitive pH fluorescent probe.

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Abstract

The invention discloses 2-pyridine vinyl naphthalimide fluorescent dendrimer (PAMAM-VPN) which is formed by connecting four naphthalimide fluorophores with polyamide-amine as a framework. The invention further discloses a preparation method of PAMAM-VPN. In an inert atmosphere, 4-(2-pyridine vinyl)0-1,8-anhydrde naphthalene and polyamide-amine reflux in methyl alcohol to have an anhydride ammonolysis reaction, and 2-pyridine vinyl naphthalimide fluorescent dendrimer is obtained after reduced pressure distillation, column chromatography purification and recrystallization. PAMAM-VPN is a fluorescent material with good performance and has extremely important application value in the fields of fluorescent probes, fluorescent sensors, biological fluorescent marks, live cell imaging and the like. The fluorescent dendrimer can serve as a bovine serum albumin fluorescent probe and a sensitive pH fluorescent probe, has an aggregation-induced emission characteristic, can serve as an aggregation-induced emission material, and can be used for live cell fluorescence imaging as fluorescent dye.

Description

technical field [0001] The invention relates to the technical field of naphthalimide fluorescent molecules, in particular to a 2-pyridylvinylnaphthimide fluorescent dendrimer connected by a polyamide-amine skeleton and a preparation method and application thereof. Background technique [0002] Naphthalimide derivatives have strong fluorescence emission, good photostability and chemical stability, high fluorescence quantum yield and large Stokes shift, and are used in fluorescent probes, chemical sensors, and bioluminescent labels. And other fields have important application prospects, and related experimental and theoretical research has attracted extensive attention. Most of the naphthalimide derivatives reported in the literature have good fluorescence properties in dilute solutions, but in the aggregated state due to intermolecular interactions that lead to non-radiative energy conversion or the formation of species that are not conducive to fluorescence emission, resulti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C09K11/06C09B23/16G01N21/64A61K49/00
CPCA61K49/00C07D401/14C09B23/164C09K11/06C09K2211/1022C09K2211/1033G01N21/64
Inventor 钱鹰胡秀东孙京府
Owner SOUTHEAST UNIV
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