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Perylene-cyclodextrin nano supermolecule assembly, as well as preparation and application thereof

A supramolecular assembly, perylene diimide technology, which can be used in material excitation analysis, fluorescence/phosphorescence, etc., can solve the problem of no fluorescence response, and achieve the effect of broad application prospects.

Inactive Publication Date: 2009-05-20
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few studies on perylene as a fluorescent sensing material. In 2008, Zang Ling et al. reported the recognition of organic amine gas molecules by nano-supramolecular assemblies constructed of perylene (Y.Chen, X.Yang, S.Loser, L.Zang.Nano Lett.2008, 8, 2219-2223.), but no fluorescence response to nitro compounds, such as nitromethane and nitrobenzene

Method used

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  • Perylene-cyclodextrin nano supermolecule assembly, as well as preparation and application thereof
  • Perylene-cyclodextrin nano supermolecule assembly, as well as preparation and application thereof
  • Perylene-cyclodextrin nano supermolecule assembly, as well as preparation and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of Perylene Diimide Derivatives Modified by Permethylated β-Cyclodextrin

[0034]The synthetic route of the fully methylated β-cyclodextrin modified perylene diimide derivatives is as follows Figure 14 shown.

[0035] at room temperature will

[0036] 6-deoxy-6-amino-permethylated-β-CD (0.94g, 0.67mmol),

[0037] Perylenetetracarboxylic anhydride (130mg, 0.33mmol) and zinc acetate (0.073g, 0.33mmol)

[0038] Added to 200 ml of pyridine solution;

[0039] The reaction system was heated to 100°C and kept at 100°C for 48 hours. The reaction was stopped, cooled to room temperature, and pyridine was evaporated under reduced pressure to obtain a red solid. Dissolve the red solid in chloroform, add a small amount of water to wash away zinc acetate, dry the chloroform phase with anhydrous sodium sulfate for 12 hours, filter to remove sodium sulfate, concentrate the chloroform phase, pass through a silica gel column, and use chloroform / methanol (volume ratio 30 / 1...

Embodiment 2

[0042] Study on the Assembly Process of Nanosupramolecular Assemblies in Aqueous Solution

[0043] in CDCl 3 In the solvent, the 8 H on the perylene aromatic ring split into four sharp peaks, indicating that in CDCl 3 PTCDI 1 is in the monomer state in the solvent, but in D 2 In the solvent of O, the four sharp peaks change into two sets of broad peaks, which is due to the strong π-π stacking effect, indicating the formation of supramolecular assemblies ( figure 1 ). The concentration of PTCDI 1 ranged from 3.0×10 -6 M changes to 1.0×10 -4 M, the extinction coefficient of the electronic transition 0-0 peak is significantly reduced, and a new shoulder peak appears at the long wavelength of 560nm ( figure 2 ). at 7.4 x 10 -5 Under the condition of M, when the temperature rises from 5°C to 70°C, it can be clearly seen that the extinction coefficient of the 0-0 peak of the electronic transition increases significantly, and the shoulder peak at 560nm gradually decreases, in...

Embodiment 3

[0045] Morphology and Optical Properties of Nanosupramolecular Assemblies

[0046] Figure 4 with Figure 5 The characteristics of the transmission electron microscope (TEM) and scanning electron microscope (SEM) of PTCDI 1, respectively, can clearly see the formation of one-dimensional rod-like assemblies. Image 6 It is an X-ray powder diffraction pattern, three groups of obvious peaks and some small peaks indicate that PTCDI 1 is a highly ordered crystal. Figure 7 with Figure 8 Polarizing and fluorescence microscopy characterization of PTCDI 1, respectively. Under crossed polarized light, very bright rod-like crystals can be seen, indicating that the optical axis of PTCDI 1 is parallel to the axis of π-π stacking of perylene molecules. Under a fluorescence microscope, strong red rod-like assemblies can be seen, indicating that they have very strong fluorescence in the solid state.

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Abstract

The invention pertains to the technical field of nanometer supramolecular materials, and relates to a nanometer supramolecular assembly of a perylene diimide derivate modified by full methylated Beta-cyclodextrin loaded by polyvinylidene fluoride membrane and a preparation method thereof. The chemical formula of the molecular assembly is C138H226N2O72, and the structure thereof is shown as in an attached drawing. The perylene diimide derivate modified by the red fully methylated Beta-cyclodextrin is dissolved to obtain the nanometer supramolecular assembly. The method adopts the strong fluorescence of solid perylene as a detecting singnal, takes an empty chamber of the fully methylated Beta-cyclodextrin as a receptor of an air molecule, thereby solving two difficulties of strong fluorescence in a solid state in the construction of a fluorescence sensor and the introduction of a suitable air molecular receptor. The nanometer supramolecular assembly of the perylene diimide derivate modified by full methylated Beta-cyclodextrin loaded by PVDF member realizes quick detection of the fluorescence sensing function of the air molecules of nitromethane, nitroethane and nitrobenzene in 10s.

Description

【Technical field】 [0001] The invention belongs to the technical field of nano-supramolecular materials, and relates to a perylene diimide derivative nano-supramolecular assembly loaded with fully methylated β-cyclodextrin on a PVDF membrane and a preparation method thereof. 【Background technique】 [0002] The construction and application of fluorescent sensors under solid-state conditions are research hotspots in recent years. The construction of fluorescent sensors to realize the recognition of gas molecules, especially the recognition of volatile flammable and explosive nitro compounds has made great progress (S.W.Thomas III, G.D.Joly, T.M.Swager.Chem.Rev.2007 , 107, 1339-1386; (2) D.T.McQuade, A.E.Pullen, T.M.Swager.Chem.Rev.2000, 100, 2537-2574; (3) S.J.Toal, W.C.Trogler.J.Mater.Chem., 2006, 16 , 2871-2883.). Two problems need to be overcome in the construction of fluorescent sensors: one is to synthesize organic compounds with strong fluorescence under solid-state con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16C08J3/03C08L5/16G01N21/64
Inventor 刘育王克让郭东升蒋邦平
Owner NANKAI UNIV
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