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A 3D cross-linked supramolecular polymer based on pillar [n] arene conjugated polymer and its preparation method and application

A supramolecular polymer and conjugated polymer technology, applied in chemical instruments and methods, information-carrying cards, luminescent materials, etc., to achieve good luminescent properties, novel mechanism of action, and good fatigue resistance.

Active Publication Date: 2021-09-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the realization of rewritable and encrypted writing by supramolecular host-guest complexation

Method used

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  • A 3D cross-linked supramolecular polymer based on pillar [n] arene conjugated polymer and its preparation method and application
  • A 3D cross-linked supramolecular polymer based on pillar [n] arene conjugated polymer and its preparation method and application
  • A 3D cross-linked supramolecular polymer based on pillar [n] arene conjugated polymer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A linear conjugated polymer host H(R 1 is methoxy; n=5; A 1 For the synthesis of triazole), the synthetic route is as follows:

[0046]

[0047] Concrete synthetic steps are as follows:

[0048] (1) Synthesis of compound 2:

[0049]

[0050] Compound 1 (1737.8mg, 2mmol), 4-aminophenylboronic acid pinacol ester (525.8mg, 2.4mmol), potassium carbonate (2764.2mg, 20mmol), Pd (pph 3 ) 4 (115,6mg, 0.1mmol) and H 2 O (10ml) was dispersed in 40ml THF. The mixture was degassed with nitrogen and stirred at 90 °C for 12 hours (stirrer rate range 500 rpm). The mixture was dried under reduced pressure (the pressure of reduced pressure was 0.09Map), and then purified by column chromatography (petroleum ether / dichloromethane / ethyl acetate: 10 / 2 / 1) to obtain compound 2 white powder (1310.1mg , 1.5mmol), yield 75%.

[0051] Compound 2 melting point data: M.p.152.2–153.0°C.

[0052] Compound 2 H NMR spectrum data: 1 H NMR (400MHz, CDCl 3 ,298K),δ(ppm):6.96(s,2H),6.82(d,...

Embodiment 2

[0065] The conjugated guest molecule G(R 2 Branched isooctyl; A 2 For the synthesis of thiophene ring), the synthetic route is as follows:

[0066]

[0067] Concrete synthetic steps are as follows:

[0068] Synthesis of conjugated guest molecule G:

[0069]

[0070] Compound 4 (1153.2mg, 1.5mmol), 5-azidovaleronitrile (744.6mg, 6mmol) and CuBr (21.5mg, 0.15mmol) were added to 20mL degassed THF, nitrogen protection. The mixture was stirred at room temperature (please stir at 500 rpm) for 12 hours, poured into brine (100 mL), and extracted with dichloromethane. The organic layer was dried under vacuum with a rotary evaporator (vacuum degree 0.09Mpa), and recrystallized in ethanol to obtain product G (1050.1mg, 1.28mmol) with a yield of 85% as a dark purple powder.

Embodiment 3

[0072]The conjugated polymer host molecule H and the conjugated guest molecule G prepared in Examples 1 and 2 were respectively subjected to UV-visible absorption light test and fluorescence emission spectrum test (10 μM chloroform solution, room temperature), and the measured UV-visible absorption Spectral and fluorescence emission spectral overlay plots, such as figure 1 shown.

[0073] From figure 1 It can be seen that the fluorescence emission of the conjugated polymer host molecule H overlaps well with the ultraviolet absorption spectrum of the conjugated guest molecule G, indicating that the conjugated polymer host molecule H and the conjugated guest molecule G have good FRET conditions, and the energy can be From the host molecule H to the guest molecule G.

[0074] Mix the conjugated polymer host molecule H prepared in Examples 1 and 2 with the conjugated guest molecule G according to the molar ratio H:G=100:1 to prepare a column [5] aromatic hydrocarbon conjugated p...

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Abstract

The invention discloses a 3D cross-linked supramolecular polymer based on a pillar [n] aromatic hydrocarbon conjugated polymer, a preparation method and an application thereof. The preparation method includes the following steps: mixing conjugated polymer host molecules and conjugated guest molecules in a certain ratio to form the 3D cross-linked supramolecular polymer based on pillar [n]arene conjugated polymers. The polymer provided by the present invention has good film-forming properties. The host and guest molecules are energy donors and acceptors respectively. Through the antenna effect and fluorescence resonance energy transfer (FRET) mechanism, energy can be transferred from the host to the guest, reflecting the color; according to the properties of the column[n]arene conjugated polymer 3D crosslinked supramolecular polymer in liquid environment and solid state, its thin film and sprayed load exhibit multi-stimulus discoloration properties, which can be used as erasable Write, encrypt written materials.

Description

technical field [0001] The present invention relates to the technical field of supramolecular self-assembly materials and organic luminescent materials, in particular to a 3D cross-linked supramolecular polymer based on pillar [n] arene conjugated polymer and its preparation method and its application in rewritable materials and encrypted writing in the application. Background technique [0002] Rewritable optical materials have attracted widespread attention due to their potential applications in data storage, information encryption, and signal switching. Existing rewritable optical materials are mainly based on light-to-color switch molecules, such as diarylethene, spiropyran, azobenzene, etc. The light-to-color-changing molecule itself has strong photosensitivity, and it is prone to cis-trans conversion or switching rings under light, which makes the stored information invalid; its fatigue resistance also needs to be improved. It is necessary to develop a new type of du...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00C08J3/24C09K11/06B42D25/36B42D25/415
CPCB42D25/36B42D25/415C08G83/008C08J3/24C08J2387/00C09K11/06C09K2211/1425C09K2211/1458C09K2211/1466
Inventor 曹德榕许林贤唐浩汪凌云
Owner SOUTH CHINA UNIV OF TECH
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