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Preparation method and application of different structural framework metalloporphyrin metal complexes

A metal complex and porphyrin technology, applied in the application field of porphyrin metal complex materials, can solve the problems of high excitation light energy, difficult adjustment of photosensitizer performance, low up-conversion quantum efficiency, etc., and achieve long triplet lifetime, The effect of rich photophysical properties, strong visible light and near-infrared light absorption ability

Active Publication Date: 2018-07-17
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many defects in these up-conversion technologies. For example, the required excitation light energy is high, generally 106W / cm 2 , much higher than the radiant energy of sunlight on the surface (100mW / cm 2 ), the solar energy standard on the ground adopts AM 1.5G), in addition, the low quantum efficiency of up-conversion, the difficulty of adjusting the performance of photosensitizers, etc., all make these technologies difficult to be practical

Method used

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  • Preparation method and application of different structural framework metalloporphyrin metal complexes
  • Preparation method and application of different structural framework metalloporphyrin metal complexes
  • Preparation method and application of different structural framework metalloporphyrin metal complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Complex P 1 Synthesis

[0031]

[0032] (1) Synthesis of 4-trimethylsilylethynyl benzaldehyde

[0033] Add p-bromobenzaldehyde (1.85g, 10mmol) in the two-necked flask, Pd(PPh 3 ) 4 (0.35g, 0.3mmol), Cul (57mg, 0.3mmol). Install backflow device seal, vacuum drum N 2 , join drum N 2 Diisopropylamine (5ml) and trimethylsilylacetylene (2.0ml, 15mmol) for 15min. The condensed water was refluxed and stirred for 2 hours at 80°C. After the reaction was completed, silica gel powder was added, spin-dried to form a powder, and the sample was loaded through the column with dichloromethane:petroleum ether (5:1) dry method, and spin-dried to obtain a white solid. Yield: 85%. 1 HNMR (400MHz, CDCl 3 )δ10.00(s,1H), 7.83–7.80(m,2H), 7.62–7.59(m,2H), 0.28–0.26(m,9H).

[0034] (2)Z 1 Compound preparation

[0035] Add pentafluorobenzaldehyde (1.48g, 7.5mmol) and 4-trimethylsilylethynylbenzaldehyde (0.51g, 2.5mmol) into a 1000ml two-necked bottle, seal and vacuum pu...

Embodiment 2

[0042] Example 2: Complex P 2 Synthesis

[0043]

[0044] (1) Compound Z 4 Synthesis

[0045] Add Z to the two-necked flask 2 (91mg, 0.1mmol), Pd(PPh 3 ) 4 (3.5mg, 0.003mmol), 9,10-dibromoanthracene (8.4mg, 0.025mmol) were sealed, vacuumed and blown nitrogen three times, injected 8ml of toluene and 2ml of triethylamine for 15min. The condensed water was refluxed and reacted at 80°C for 48 hours. After the reaction, silica gel powder was added and spin-dried to form a powder. The sample was loaded through the column with dichloromethane:petroleum ether (8:1) dry method and spin-dried to obtain an orange solid. 1 H NMR (400MHz, CDCl 3 )δ9.09(d, J=4.6Hz, 4H), 8.98(dd, J=6.7, 3.3Hz, 4H), 8.91(dd, J=11.1, 4.0Hz, 12H), 8.36(d, J=8.1 Hz, 4H), 8.27 (d, J=8.1Hz, 4H), 7.84 (dd, J=6.8, 3.1Hz, 4H), -2.80 (s, 4H).

[0046] (2) Complex P 2 Synthesis

[0047] Add Z to the two-necked flask 4 (50mg, 0.025mmol) zinc acetate (183mg, 1mmol) was added to dichloromethane 3ml, methanol...

Embodiment 3

[0048] Example 3: Compound P 3 Synthesis

[0049]

[0050] (1) Compound Z 7 Synthesis

[0051] Add pentafluorobenzaldehyde (1.48g, 7.5mmol) and p-iodobenzaldehyde (0.58g, 2.5mmol) into a 1000ml two-necked bottle, seal and vacuumize and blow nitrogen three times. Add 800ml of redistilled dichloromethane, then inject pyrrole (1.04ml, 15mmol), blow nitrogen gas for 15min, add boron trifluoride ether (1.2ml, 5mmol) and the solution will slowly turn red, and add two Chlorodicyanobenzoquinone (DDQ) (1.20 g, 5 mmol) turned black. Two hours later, 0.8 ml of triethylamine was added. After two hours of filtration, the collected filtrate was spin-dried and passed through the column. Dichloromethane:petroleum ether (15:1) was dry-loaded through the column, and spin-dried to obtain a purple-red solid. 1 H NMR (400MHz, CDCl 3 )δ8.86 (ddd, J=18.5, 14.2, 4.8Hz, 8H), 8.12 (dd, J=8.4, 2.0Hz, 4H), 7.97–7.92 (m, 4H), -2.86 (d, J=22.7 Hz, 2H).

[0052] (2) Compound Z 5 Synthesis

[00...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and concretely relates to synthesis and application of porphyrin metal complexes with different frameworks. The complexes are obtained through coordination of porphyrin rings with different structures and a metal, and the structure general formula is shown in the specification. A porphyrin compound is synthesized from pyrrole, pentafluorobenzaldehyde and trimethylsilylacetylene, and then porphyrin complexes are formed through coordination of the porphyrin compound and different metals. TTA (triplet-triplet annihilation) transition phenomenon is generated when the prepared target metal complex is combined with an acceptor, and the metal complexes have good application prospects on solar cells and cell imaging. Additionally, the porphyrin metal complexes can generate single oxygen quantum dot with extremely high efficiency, and possesses potential application prospect on anoxia detection and photodynamic therapy. The prepared target complexes are shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to the application of a class of porphyrin metal complex materials with TTA effect. Background technique [0002] Up-conversion is a technology that converts low-energy (long-wavelength) light into high-energy (short-wavelength) light through a multi-photon mechanism. The potential application value has attracted extensive attention. At present, there are many technologies for realizing up-conversion, such as using dyes with large two-photon absorption cross section to realize two-photon up-conversion, or using rare earth materials to realize up-conversion of light wave frequency, etc. However, there are many defects in these up-conversion technologies. For example, the required excitation light energy is high, generally 106W / cm 2 , much higher than the radiant energy of sunlight on the surface (100mW / cm 2 ), the solar energy standard on the gro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/31
CPCC07D487/22C09K11/06C09K2211/1466C09K2211/188G01N21/31
Inventor 赵强黄维江鹏飞周晓波刘淑娟许文娟
Owner NANJING UNIV OF POSTS & TELECOMM
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