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Fluorescent conjugated polymer containing spiropyran side group as well as preparation method and application of fluorescent conjugated polymer

A technology of conjugated polymer and spiropyran, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of single structure, difficulty in applying dynamic anti-counterfeiting, lack of photochromism, etc., and achieve easy operation quick effect

Active Publication Date: 2021-12-17
SUZHOU UNIV +1
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  • Application Information

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Benefits of technology

This patented method allows for creating an antiforge material with unique properties through copolymering certain types of molecules called pyrroles or spiral chromophores together into one long chain structure. These materials can emit different colors when exposed to specific wavelengths of ultraviolet rays (UVR). They are also very secure because they cannot easily replicate their original design without being copied again. Additionally, these methods allow for efficient production processes at room temperature while maintaining high efficiency during use over several months' storage period.

Problems solved by technology

This patents discuss how current antiflamination systems used for security purposes involve expensive specialized material and require long periods of production. Additionally, existing techniques like adding quantum dots suffer from challenges related to achieving stable multi-dimensional features over longer times without losing important functions during prolonged exposure.

Method used

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  • Fluorescent conjugated polymer containing spiropyran side group as well as preparation method and application of fluorescent conjugated polymer
  • Fluorescent conjugated polymer containing spiropyran side group as well as preparation method and application of fluorescent conjugated polymer
  • Fluorescent conjugated polymer containing spiropyran side group as well as preparation method and application of fluorescent conjugated polymer

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0044] This example provides a method for synthesizing a fluorescent conjugated polymer containing spiropyran side groups denoted as PPETE-SP.

[0045] 1. Preparation of monomer M1:

[0046] In this example, the monomer M1 uses 2,5-dibromohydroquinone as the raw material, introduces long alkyl side chains through nucleophilic substitution and esterification reactions, and then introduces alkynyl groups through coupling reactions. Its structural formula is :

[0047] ;

[0048] The specific synthetic steps can be found in the literature ( ACS Appl. Mater. Interfaces 2014, 6, 5041-5049).

[0049] 2. Preparation of monomer M2:

[0050] See attached figure 1 , is a schematic diagram of the synthesis route of monomer M2 provided in this example; in this example, compound 1 is (6-((2,5-dibromothiophen-3-yl)methoxy)-6-oxohexyl acid), its structural formula is:

[0051] ;

[0052] Its synthetic method can refer to literature ( ACS Appl. Mater. Interfaces 2017, 9, 309...

Embodiment 2

[0067] This embodiment provides a dynamic fluorescent anti-counterfeiting fiber membrane of a fluorescent conjugated polymer containing spiropyran side groups and its preparation.

[0068]The fluorescent conjugated polymer PPETE-SP containing spiropyran side groups synthesized in Example 1 and the polymethyl methacrylate matrix were dissolved in N,N-Di In methylformamide (3.5mL), the mixed solution was stirred at 50°C for 3 hours to obtain a homogeneous mixed spinning stock solution. The spinning stock solution was injected into a 10mL syringe, and the electric field was applied at 10KV, and the distance between positive and negative electrodes was 10cm. The dynamic fluorescent anti-counterfeiting fiber film of the fluorescent conjugated polymer containing the spiropyran side group is obtained by using the electrospinning process.

[0069] See attached Figure 6 , which is a scanning electron micrograph of the dynamic fluorescent anti-counterfeiting fiber membrane prepared in...

Embodiment 3

[0074] This example provides a dynamic fluorescent anti-counterfeiting application method using the fluorescent fiber membrane prepared in Example 2. The specific steps are: first use a digital camera to record the color and ultraviolet (365 nm, 6W) excitation of the fiber membrane in its initial state Then irradiate the fluorescent fiber membrane under ultraviolet light (365nm, 6W) for 60s, record the color and fluorescence emission after ultraviolet irradiation, and finally irradiate with visible light (white light, 5W) for 60s, record the color and Fluorescence emission, contrasting photo color changes before and after UV / Vis exposure, respectively.

[0075] See attached Figure 10 and 11 , Figure 10 It is a photo of the color change of the fiber membrane used for fluorescent anti-counterfeiting by the dynamic fluorescent anti-counterfeiting fiber membrane, Figure 10 Among them, ①③ is the digital photo of the color of the fiber membrane under natural light, ②④ is the d...

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Abstract

The invention relates to a fluorescent conjugated polymer containing a spiropyran side group as well as a preparation method and an application of the fluorescent conjugated polymer. The preparation method comprises the following steps: preparing a fluorescent conjugated polymer containing a spiropyrane side group through a Sonogashira coupling method, combining the fluorescent conjugated polymer with a polymethyl methacrylate matrix, and adopting an electrostatic spinning process to obtain the fluorescent fiber membrane with photochromic performance. Under the excitation of ultraviolet light, the fluorescent fiber membrane emits yellow fluorescence of 480-550 nm, and after the fluorescent fiber membrane is continuously irradiated by using ultraviolet light of 365 nm for a period of time, the yellow fluorescence is converted into red fluorescence of 600-700 nm; and after the visible light is used for continuously irradiating for a period of time, the red fluorescence excited by the ultraviolet light is recovered to yellow fluorescence. The fluorescent conjugated polymer provided by the invention has the characteristics of simple synthesis conditions, high reaction yield and high fluorescence quantum efficiency, and can be applied to the field of dynamic fluorescent falsification prevention.

Description

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Claims

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Application Information

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Owner SUZHOU UNIV
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