Perylene imide bridge type dimethylate-ethylenediamine-Beta-cyclodextrin derivate, preparation and applications thereof

A technology of peryleneimide bridge and ethylenediamine group, which is applied in the cross-research fields of chemistry, materials and nanotechnology, and can solve the problems of unreported research on peryleneimide derivatives

Inactive Publication Date: 2009-10-14
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, studies on cyclodextrin-modified peryleneimide derivatives have not been reported

Method used

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  • Perylene imide bridge type dimethylate-ethylenediamine-Beta-cyclodextrin derivate, preparation and applications thereof
  • Perylene imide bridge type dimethylate-ethylenediamine-Beta-cyclodextrin derivate, preparation and applications thereof
  • Perylene imide bridge type dimethylate-ethylenediamine-Beta-cyclodextrin derivate, preparation and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of peryleneimide-bridged bispermethylated-ethylenediamine-β-cyclodextrin derivatives

[0041] The synthetic route of peryleneimide bridged double permethylated-ethylenediamine-β-cyclodextrin derivatives is as follows Figure 20 shown.

[0042] at room temperature will

[0043] 6-deoxy-6-ethylenediamino-permethylated-β-cyclodextrin (0.98g, 0.67mmol),

[0044] Perylenetetracarboxylic anhydride (130mg, 0.33mmol) and zinc acetate (0.073g, 0.33mmol)

[0045] Added to 200 ml of pyridine solution;

[0046] The reaction system is heated to 80-120°C and kept at 80-120°C for 48-72 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 c...

Embodiment 2

[0049] Aggregation Behavior of PTCDI 2 in Different Solvents

[0050] In organic solvents such as chloroform, toluene, acetone, acetonitrile, etc., PTCDI 2 presents the characteristic of ultraviolet absorption spectrum of a typical monomer, and its A 0-0 / A 0-1 Respectively 1.52 (chloroform), 1.44 (toluene), 1.40 (acetone), 1.35 (acetonitrile), and in the methanol solution, it is the spectral characteristic of monomer to dimer transformation, its A 0-0 / A 0-1 is 1.22, the maximum absorption peak is around 520nm for the 0-0 peak, and around 490nm for the 0-1 peak. However, in aqueous solution, the absorption intensity of the 0-0 peak decreases significantly, and the 0-1 peak becomes the strongest absorption peak, red shifted to 497nm, and its A 0-0 / A 0-1 reduced to 0.68, which is the characteristic absorption spectrum of the aggregate state, such as figure 1 a, At the same time, the fluorescence intensity of PTCDI 2 in aqueous solution is obviously weaker than that in org...

Embodiment 3

[0052] Spectral study of PTCDI 2 before and after protonation

[0053] PTCDI 2 at a concentration of 1.0 x 10 -5 In the chloroform solution of M, trifluoroacetic acid is added to protonate the imine group, and the A of PTCDI 2 before and after protonation 0-0 / A 0-1 The ratio of PTCDI2 is basically unchanged, indicating that PTCDI2 exists in the form of monomer in chloroform solution before and after protonation, but the intensity of its fluorescence spectrum is enhanced by nearly 4 times, which is because the imino group on PTCDI2 is no longer an electron donor after protonation. body, intramolecular photoinduced electron transfer is blocked, so the fluorescence is enhanced ( image 3 ). The UV-Vis spectrum research under different pH values ​​found that as the pH value decreased, the UV-Vis spectrum of PTCDI 2 changed significantly, and the peak shape narrowed, 0-0 peak (530nm) and 0-1 peak (496nm ) increased significantly, but the 0-0 peak increased much more than the 0...

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Abstract

The invention relates to perylene imide bridge type dimethylate-ethylenediamine-Beta-cyclodextrin derivate, and synthesis. The chemical formula of the derivate is C152H236N4O72, and the structure is shown in an attached drawing. The compound self-assembles into nano spherical aggregates, the electrostatic repulsion between molecules is increased by protonizing imino so as to disaggregate supermolecule aggregates, and simultaneously photoinduced electron transferring process in the molecules is blocked so as to generate strong fluorescence, thereby realizing aggregation behavior of pH value control and change of optical property. In the compound, cyclodextrin is taken as a receiver of specific molecules, the perylene with excellent optical property is taken as a detector which can optically sense water-soluble aromatics guest molecules (benzene sulfonic acid sodium salt, 2-naphthalenesulfonic acid sodium salt, 2-anthroic acid sodium salt and pyrenebutyric acid sodium salt), and the guest molecule module structure is shown in the attached drawing.

Description

【Technical field】 [0001] The invention belongs to the interdisciplinary research fields of chemistry, materials and nanotechnology, and relates to the synthesis of peryleneimide bridged bicyclodextrin derivatives, the construction of aggregates and its sensing. 【Background technique】 [0002] In recent years, the use of aromatic compounds in aqueous solution to construct highly ordered functionalized nano-supramolecular assemblies and selective sensing has become a research hotspot in the fields of chemistry, biology and materials (A.Ajayaghosh, V.K.Praveen.Acc.Chem. Res.2007, 40, 644-656; (2) A.C.Grimsdale, K.Müllen.Angew. Schenning. Chem. Soc. Rev. 2009, 38, 671-683; (4) K. T. Chem.Commun.2005, 1812-1823. (e) J.H.Ryu, D.J.Hong, M.Lee.Chem.Commun.2008, 1043-1054.). The interaction of excited state electrons between adjacent large π compound molecules may lead to novel nano-supramolecular materials with special optoelectronic properties. Among various aromatic building...

Claims

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Application Information

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