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Preparation method of fluorescein-functionalized polydiacetylene vesicles with adjustable colorful fluorescence emission and construction of molecular logic gate

A fluorescence emission, polydiacetylene technology, applied in chemical instruments and methods, luminescent materials, etc., can solve the problems of low sensitivity of functionalized substrates, high pH control requirements, complicated preparation conditions, etc., and achieves strong anti-environmental interference ability, The system is responsive and the operation is simple.

Active Publication Date: 2021-07-27
NORTHEAST FORESTRY UNIVERSITY
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Problems solved by technology

[0004] In order to solve the problems of cumbersome preparation conditions, high pH control requirements, low sensitivity of the functionalized substrate, and large interference from the outside world for the existing fluorescence-regulated functionalized substrate, the present invention provides a multicolored fluorescent emission controllable substrate. Preparation of fluorescein-functionalized polydiacetylene vesicles and construction of molecular logic gates

Method used

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  • Preparation method of fluorescein-functionalized polydiacetylene vesicles with adjustable colorful fluorescence emission and construction of molecular logic gate
  • Preparation method of fluorescein-functionalized polydiacetylene vesicles with adjustable colorful fluorescence emission and construction of molecular logic gate
  • Preparation method of fluorescein-functionalized polydiacetylene vesicles with adjustable colorful fluorescence emission and construction of molecular logic gate

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specific Embodiment approach 1

[0032] Embodiment 1: A method for preparing fluorescein-functionalized polydiacetylene vesicles that can regulate colorful fluorescence emission. The specific process of the method is as follows:

[0033] (1) Add 5(6)-carboxyfluorescein and ethylenediamine with a molar ratio of 1:1.2 to absolute ethanol, heat to reflux at 80°C for 12 hours, cool to room temperature, filter, and wash with absolute ethanol for 2- 3 times, recrystallized to obtain aminated fluorescein (FDNS), the synthetic formula of FDNS is as follows figure 1 As shown, the structural formula and NMR spectrum of FDNS are as follows figure 2 As indicated, the deuterated reagent used was deuterated dimethyl sulfoxide (d-DMSO) with a chemical shift of 2.54 ppm. Hydrogen atoms on the benzene ring can be found in the 8ppm, 7.7ppm, 7.2ppm, and 6.5ppm regions of the H NMR spectrum; the 4.2ppm region is the hydrogen atom on the phenolic hydroxyl group; the 3.2ppm and 1.2ppm regions are the adjacent carbons of the amin...

specific Embodiment approach 2

[0037] Specific embodiment 2: Fluorescence regulation method of blue polydiacetylene complex vesicles, such as Figure 7 as shown,

[0038] ①. Heat the blue polydiacetylene complex vesicle system prepared in Embodiment 1 to 80°C, so that the polydiacetylene becomes a red phase with fluorescence, and the system produces a single red fluorescence emission.

[0039] 2. Add a certain amount of L-lysine and Cu to the blue polydiacetylene complex vesicle system prepared in Embodiment 1 2+ ions, the basic amino acid in the system will slightly increase the pH, and the fluorescein group will respond, but the polydiacetylene is still in the blue phase state, so the system presents green fluorescence emission.

[0040] ③. On the basis of ②, heat the system to 80°C to make the polydiacetylene turn into a red phase with fluorescence, and the fluorescein produces green fluorescence emission. The two kinds of fluorescence are mixed, and the system presents yellow fluorescence emission.

...

specific Embodiment approach 3

[0044] Specific embodiment 3: The construction of molecular logic gates of fluorescein-functionalized polydiacetylene vesicles that can regulate colorful fluorescence emission, the construction process is as follows:

[0045] OR logic gate: for fluorescein-modified diacetylene vesicles, define the input signal (input): L-amino acid (L-lysine) or heating (heating) is 1, otherwise it is 0; output (output): yellow The polydiacetylene vesicle system in the fluorescence emission state is 1, otherwise it is 0. Define polydiacetylene vesicles as the blue phase state and the system as the initial state of green fluorescence emission, so when the system has L-amino acid (L-lysine) or heating (heating) as the input signal, the input When the signal is (1 / 0, 0 / 1, 1 / 1), the compound polydiacetylene vesicle device can realize yellow fluorescence emission, that is, the output signal is 1, such as Figure 8 As shown, the OR logic gate can be used as a sensitive device for regulating colorfu...

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Abstract

A preparation method of fluorescein-functionalized polydiacetylene vesicles capable of regulating colorful fluorescence emission and the construction of molecular logic gates belong to the technical field of organic conjugated polymer wave assembly. The present invention aims to solve the problems of cumbersome preparation conditions, high pH control requirements, low sensitivity of the functionalized substrate, and greater external interference of the existing fluorescence-regulated functionalized substrate. In the present invention, diacetylene and fluorescein groups are combined to obtain polydiacetylene composite vesicles. The composite vesicles are based on the phase transition of red phase and blue phase of polydiacetylene under external stimulation, and the effect of fluorescein groups on the pH value of the outside world. To realize the multi-stimulation polydiacetylene and fluorescein groups, both the color and the fluorescent emission change regulation of the multicolored fluorescence emission method. The composite vesicle of the invention has a simple preparation process, excellent fluorescence controllable performance, simple and convenient fluorescence control operation process, strong operability, strong resistance to environmental interference, and sensitive and rapid system response.

Description

technical field [0001] The invention relates to a preparation method of a fluorescein-functionalized polydiacetylene vesicle capable of regulating and controlling colorful fluorescence emission and the construction of a molecular logic gate, belonging to the technical field of organic conjugated polymer wave assembly. Background technique [0002] Multiple stimuli-responsive fluorescent polymers have the advantages of good fluorescence emission, easy preparation, and stable performance, and have broad prospects in biosensors, display materials, logic switches, and information storage. [0003] When polydiacetylene is stimulated by many external environments, such as temperature, pH, chemical reagents and stress, etc., there will be obvious color changes visible to the naked eye, and the typical color change is from blue to red. However, at present, the regulation of fluorescence emission mostly depends on methods such as light, heat, electricity, and chemical substances, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F238/00C08F2/48C09K11/06
CPCC08F2/48C08F238/00C09K11/06C09K2211/1029C09K2211/1088
Inventor 杨光侯娟李光耀纪捷
Owner NORTHEAST FORESTRY UNIVERSITY
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