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Super-phthalocyanine compound with six isoindole structure subunits in laver oxazine cycle and its synthesis and use

A compound and element technology, applied in copper organic compounds, nickel organic compounds, cobalt organic compounds, etc.

Inactive Publication Date: 2004-11-24
杜锡光 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Superphthalocyanines with six isoindole structural subunits in the porphyrazine ring have not been reported

Method used

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  • Super-phthalocyanine compound with six isoindole structure subunits in laver oxazine cycle and its synthesis and use
  • Super-phthalocyanine compound with six isoindole structure subunits in laver oxazine cycle and its synthesis and use
  • Super-phthalocyanine compound with six isoindole structure subunits in laver oxazine cycle and its synthesis and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Compound 1a 1 Synthesis

[0053] Choose A in general formula (1) 1 and A 4 stands for nitrogen atom, A 2 and A 3 stands for carbon atom, R 1 and R 4 Does not represent any group and atom, R 2 and R 3 Represents hydrogen atom, M represents Cu(II) ion, R 5 …R 6 represent

[0054]

[0055] Parts I, II, and III have the same structure and constitute compound 1a 1 , the structural formula is shown in Figure 4.

[0056] Weigh 8.0001g of urea, the compound of general formula (3) such as: 2,3-pyrazine dicarboxylic acid (Pyrazine-2,3-dicarboxylic Acid) 4.0008g (0.0238mol), CuCl 2 2H 2 O1.3683g (0.0080mol), (NH 4 ) 2 MoO 4 0.8001g is ground and mixed evenly, put into a steel bullet with a polytetrafluoroethylene lining and sealed, put the steel bullet in an oven and heat to 240°C for 8 hours; open the cover after the steel bullet cools to room temperature, and take out the black solid; This black solid is put into the vacuum purification device, in 1...

Embodiment 2

[0057] Example 2 Compound 2a 1 Synthesis

[0058] Choose A in general formula (1) 1 and A 4 stands for nitrogen atom, A 2 and A 3 stands for carbon atom, R 1 and R 4 Does not represent any group and atom, R 2 and R 3 Represents a hydrogen atom, M represents a Cu(II) ion, I, II, III, IV, V, VI have the same structure, and constitute the compound 2a of the general formula (2) 1 , the structural formula is shown in Figure 8

[0059] The general formula (1) compound 1a that will make 1 placed in a vacuum device at 10 -4 Pa, reacted for 24 hours under the condition of 500°C, and the compound 1a of general formula (1) was produced 1 After the bimolecular condensation reaction, the general formula (2) compound 2a was prepared 1 . Mass spectrometer records general formula (2) compound 2a 1 The molecular ion peak of (Figure 9) M+Na + : 931.9193 amu, close to the calculated value 930.7240, and M+H+Na + The calculated value of 931.7319 matches. This is due to the interac...

Embodiment 3

[0060] Example 3 General formula (2) compound 2a 1 UV-VIS-NIR absorption spectrum

[0061] Study on compound 2a of general formula (2) by UV-VIS-NIR spectrometer 1 UV-VIS-NIR absorption spectrum of formic acid solution ( Figure 16 ), the results show that, in addition to the common absorption peaks in the ultraviolet and visible regions of phthalocyanine, there is an absorption in the near-red region (1.428 μm), and the absorption coefficient is very large. Our observed general formula (2) compound 2a 1 The UV-VIS-NIR absorption spectrum of phthalocyanine is very different from that of general phthalocyanine. Using this property, the compound of general formula (2) can be used to prepare optoelectronic devices, especially near-infrared optoelectronic devices. Compound 2a of general formula (2) 1 When the photoactivity in the near-infrared region is used in the infrared photodynamic therapy of cancer, the light transmission process can be completed in vitro by utilizing t...

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Abstract

The super-phthalocyanine compound with six isoindole structure subunits in laver oxazine cycle has completely new phthalocyanine compound structure, and has new properties, including three strong absorption peaks in UV-VIS-NIR absorption spectrum, especially characterized NIR peak at 1428 nm; surface photovoltaic characteristic; photoluminescence characteristic; electroluminescence; very high heat stability; excellent conductivity; etc. The unique properties make the compound possess important application in several fields. The present invention increases the basic laver oxazine cycle structures in phthalocyanine compound from 3 to 4 and increases one new family for phthalocyanine compounds.

Description

Technical field: [0001] The invention relates to a class of superphthalocyanine compounds having six isoindole structural subunits in a porphyrazine ring, a synthesis method and an application thereof, and belongs to the technical field of synthesis methods of phthalocyanine compounds and preparation of related materials. Background technique: [0002] Phthalocyanine compounds are a class of widely used and very important functional molecules. At present, the application fields of phthalocyanine compounds have involved chemical sensor devices, electrophotographic materials, semiconductor devices, organic conductive materials, photodynamic therapy of cancer, solar cell materials, liquid crystal display materials, nonlinear optical materials, laser dyes, fuels, etc. Batteries, optical information storage and other fields. Since phthalocyanine was first synthesized by Braun et al. in 1907, it has formed a family with a huge number of derivatives. In this family of phthalocyan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06G03G5/06
CPCC09K2211/187G03G5/0648C07D487/22G03G5/0655C09K11/06G03G5/0646G03G5/0629G03G5/0696G03G5/0651C09K2211/1074
Inventor 杜锡光杜国同
Owner 杜锡光
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