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

A compound, pyrazine dicarboxylic acid technology, applied in cobalt organic compounds, nickel organic compounds, copper organic compounds, etc.

Inactive Publication Date: 2008-09-03
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] Select 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 or atom, R 2 and R 3 represents hydrogen atom, M represents Cu(II) ion, R 5 …R 6 represent

[0054]

[0055] The structures of parts I, II, and III are identical and constitute compound 1a 1 , the structure is shown in Figure 4.

[0056] Weigh 8.0001g of urea, compound of general formula (3) such as: 2,3-pyrazine-2,3-dicarboxylic Acid 4.0008g (0.0238mol), CuCl 2 ·2H 2 O1.3683g (0.0080mol), (NH 4 ) 2 MoO 4 0.8001g was finely ground and mixed evenly, put it into a steel bomb with a teflon lining and sealed, put the steel bomb in an oven and heated to 240°C for 8 hours; open the lid after the steel bomb cools to room temperature, and take out the black solid; The black solid was placed in a vacuum purification unit, and at 10 -4 Pa, purified at 300°C for 24 hours. Co...

Embodiment 2

[0057] Example 2 Compound 2a 1 Synthesis

[0058] Select 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 or 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, forming the compound 2a of the general formula (2) 1 , the structure is shown in Figure 8

[0059] The prepared compound 1a of general formula (1) 1 into the vacuum, at 10 -4 Pa, reacted at 500°C for 24 hours to generate compound 1a of general formula (1) 1 After the bimolecular condensation reaction of , the compound 2a of the general formula (2) was prepared 1 . The compound 2a of the general formula (2) was measured by mass spectrometer 1 The molecular ion peak of (Fig. 9) M+Na + : 931.9193amu, close to the calculated value of 930.7240, and M+H+Na + The calculated value of 931.7319 matches. This is attributed to hydrogen gas in the mass spectrom...

Embodiment 3

[0060] Embodiment 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 ), and the results show that in addition to the absorption peaks in the ultraviolet region and visible region shared by general phthalocyanines, there is an absorption in the near-red region (1.428μm), and the absorption coefficient is very large. Compound 2a of general formula (2) we observed 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 for the infrared photodynamic therapy of cancer, the light transmission process can be completed ...

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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 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 sensing 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 Batteries, optical information storage and other fields. Phthalocyanines have formed a family with a huge number of derivatives since they were first synthesized in 1907 by Braun et al. In this family of phthalocyanine c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/44C07D487/22C07F1/08C07F15/06C07F15/04C09K11/06G03G5/06
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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