Fluorescent molecular probe for Cu2+ detection as well as preparation method thereof and application thereof

A fluorescent probe and molecular technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as gastrointestinal discomfort, liver and kidney damage, etc., and achieve the effect of broad application prospects.

Inactive Publication Date: 2014-07-30
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

High concentrations of copper can cause gastrointestinal discomfort in the short term, and liver and kidney damage in the long term

Method used

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  • Fluorescent molecular probe for Cu2+ detection as well as preparation method thereof and application thereof
  • Fluorescent molecular probe for Cu2+ detection as well as preparation method thereof and application thereof
  • Fluorescent molecular probe for Cu2+ detection as well as preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The probe that the present invention relates to diaminomaleonitrile and naphthalimide combination is synthesized by the following method:

[0024] 1) Under nitrogen protection, 1.5g 4-cyano-N-n-butylnaphthalimide, 1.6g aluminum-nickel alloy, 15ml formic acid (85%), reflux (about 100°C) in 5ml deionized water for 2.5 hours, cool Afterwards, neutralize to Ph=6, extract with ethyl acetate, dry over anhydrous magnesium sulfate, perform silica gel column chromatography, eluent petroleum ether: ethyl acetate=20:1, and obtain 4-formyl-nitrogen-n-butyl - Naphthalimide, yield 50%. HNMR (CDCL3, 500HZ, δppm): 10.51(s, 1H,), 9.51(d, 1H, J=11.0), 8.75(d, 1H, J=9.0), 8.68(d, 1H, J=9.5), 8.23(d, 1H, J=9.0), 7.94(t, 1H, J=10.5), 4.20(t, 2H, J=9.0), 1.73(m, 2H), 1.45(m, 2H), 0.99(t , 3H, J=9.0).. 13 CNMR (CDCL3, TMS, 500HZ, δppm): 13.8, 20.4, 30.2, 40.5, 122.8, 127.3, 128.6, 128.9, 129.7, 129.9, 131.3, 131.7, 134.7, 135.5, 163.2, 163.8, 192.8.ESI-Ms for C 17 h 15 NO 3 , (M+H + ):...

Embodiment 2

[0028] Dissolve the fluorescent probe molecule in acetonitrile to prepare a 0.01 mM solution with 0 to 2.8 equivalents of Cu 2+ Titrate the aqueous solution, excited by 360nm light, monitor the change of fluorescence spectrum at 425nm and 522nm. Cu 2+ When the amount of ion is 0, the probe has no fluorescence, and when it is less than 1 equivalent, there is only fluorescence at 522nm ( figure 1 ), when greater than 1 equivalent, there is fluorescence at 425, and the fluorescence at 522nm gradually disappears ( figure 2 ). Firstly, the intramolecular photoelectron transfer (PET) process of the probe is blocked, and the light is emitted at 522nm. As the concentration of copper ions increases, there is an intramolecular charge transfer process (ICT), resulting in a wavelength blue shift of 425nm. When adding 1 equivalent of other metal ions to the probe solution, the change is small ( image 3 ).

[0029] In the above, a fluorescence instrument is used to monitor the response...

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Abstract

The invention belongs to the technical field of fluorescent probes for metal ion detection and in particular relates to a fluorescent molecular probe for Cu2+ detection as well as a preparation method thereof and an application thereof. According to the invention, diaminomaleonitrile, which is modified at the fourth bit of N-n-butyl-1,8-naphthalimide in the form of Schiff base, is adopted as a probe molecule. The probe molecule has no fluorescence in an acetonitrile solution; Cu2+ aqueous solution of less than 1 equivalent is added to the probe solution; due to effects of amino groups and imino groups in the Cu2+ and the probe molecule, photoinduced electron transfer (PET) process is blocked while being excited by 360 nm lights; the absorbed energy is used for emitting lights so as to emit green fluorescence; when the concentration of the Cu2+ is more than 1 equivalent, the Cu2+ begins to act on together with two cyano groups so that the electron withdrawing capability is enhanced and the emission wavelength shifts to blue. With the increasing of the concentration, green light gradually disappears and the blue light is gradually enhanced. No corresponding response is generated by adding other metal ions. According to the invention, the copper ions are specially recognized by using the probe molecule; and with the increasing of the Cu2+ concentration, the probe is correspondingly changed from no fluorescence, to green fluorescence and to blue fluorescence. The special advantage of concentration response obtains broad application prospect in the particle detection field.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes for metal ion detection, in particular to a 2+ The detected fluorescent ion probe molecule and its preparation method and application. Background technique [0002] A fluorescent probe is a molecule in a certain system, when a certain physical property of a substance or system changes, the fluorescent signal can change accordingly. Metal ion fluorescent probes provide a detection method with a wide range of applications, and the photophysical and photochemical issues involved in the design, synthesis, application and identification process have attracted extensive attention from researchers in different fields. [0003] Fluorescent ion probes have advantages that other analytical methods such as atomic absorption spectroscopy, ion selective electrode analysis and other traditional methods cannot match, that is, the existence and concentration range of ions can be intuitively reflected ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D221/14G01N21/64
Inventor 易涛兰海闯刘斌余旭东刘刻印曹新华
Owner FUDAN UNIV
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