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Preparation method for metalloporphyrin metal complexes with different structure frameworks and application

A technology of metal complexes and complexes, applied in chemical instruments and methods, color/spectral characteristic measurement, luminescent materials, etc., can solve problems such as high excitation light energy, difficult adjustment of photosensitizer performance, and low up-conversion quantum efficiency. Achieve long triplet lifetime, strong visible light and near-infrared light absorption ability, rich photophysical properties

Active Publication Date: 2016-03-30
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 AM1.5G), in addition, the low up-conversion quantum efficiency and the difficulty in adjusting the performance of the photosensitizer make these technologies difficult to be practical

Method used

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  • Preparation method for metalloporphyrin metal complexes with different structure frameworks and application
  • Preparation method for metalloporphyrin metal complexes with different structure frameworks and application
  • Preparation method for metalloporphyrin metal complexes with different structure frameworks and application

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), Pd(PPh 3 ) 4 (0.35g, 0.3mmol), CuI (57mg, 0.3mmol). Install the reflux device to seal and vacuum drum N 2 , Add drum N 2 15min of diisopropylamine (5ml) and trimethylsilylacetylene (2.0ml, 15mmol). The condensed water was refluxed and reacted with stirring at 80°C for 2 hours. After the reaction, silica gel powder was added and spin-dried to form a powder. The sample was applied to the column by the dry method of dichloromethane: petroleum ether (5:1) 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 flask. After sealing, vacuum drum nitrogen is applied and repeate...

Embodiment 2

[0042] Example 2: Complex P 2 Synthesis

[0043]

[0044] (1) Compound Z 4 Synthesis

[0045] Add Z to the two-neck bottle 2 (91mg, 0.1mmol), Pd(PPh 3 ) 4 (3.5mg, 0.003mmol), 9,10-dibromoanthracene (8.4mg, 0.025mmol) is sealed and vacuumed and bubbling with nitrogen three times, bubbling for 15min with 8ml of toluene and 2ml of triethylamine. 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 applied to the column by the dry method of dichloromethane: petroleum ether (8:1) and spin-dried to obtain an orange solid. 1 HNMR(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 = 8.1 Hz, 4H), 7.84 (dd, J = 6.8, 3.1 Hz, 4H), -2.80 (s, 4H).

[0046] (2) Complex P 2 Synthesis

[0047] Add Z to the two-neck bottle 4 (50mg, 0.025mmol) zinc acetate (183mg, 1mmol) was added to 3ml of dichloromethane and 6ml of methano...

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 flask, seal and evacuate nitrogen and repeat three times. Add 800ml of redistilled dichloromethane, then inject pyrrole (1.04ml, 15mmol), bubbling with nitrogen for 15min, add boron trifluoride ether (1.2ml, 5mmol) and the solution will slowly turn red. After one hour, add two Chlorodicyanobenzoquinone (DDQ) (1.20g, 5mmol) will turn black. After two hours, 0.8 ml of triethylamine was added. Two hours later, it was filtered and the filtrate was collected and spin-dried through the column. Dichloromethane: petroleum ether (15:1) was applied to the column by dry method and spin-dried to obtain a purple-red solid. 1 HNMR(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

[0053] Add Z t...

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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. Specifically, it relates to the application of a class of porphyrin metal complex materials with TTA effect. Background technique [0002] Upconversion is a technology that converts low-energy (long-wavelength) light into high-energy (short-wavelength) light through a multiphoton mechanism. It is used in solar cells, artificial photosynthesis, photocatalysis, and optoelectronic devices. The potential application value has received widespread attention. At present, there are many technologies for up-conversion, such as using dyes with larger two-photon absorption cross-sections to achieve two-photon up-conversion, or using rare earth materials to achieve up-conversion of lightwave frequencies. However, these up-conversion technologies have many shortcomings. For example, the required excitation light energy is high, generally 106W / cm 2 , Much higher than the radiant energy of ...

Claims

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Application Information

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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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