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Organic triplet photosensitive agent with host-guest recognition group and preparation method of organic triplet photosensitive agent

A technology of host-guest identification and triplet state, applied in the field of photosensitizers, can solve the problems of low conversion efficiency of photosensitizers, and achieve the effect of improving up-conversion efficiency

Active Publication Date: 2018-06-12
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The object of the present invention is to provide an organic triplet photosensitizer with a host-guest recognition group and its preparation method, to solve the problem of low conversion efficiency of existing photosensitizers

Method used

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  • Organic triplet photosensitive agent with host-guest recognition group and preparation method of organic triplet photosensitive agent
  • Organic triplet photosensitive agent with host-guest recognition group and preparation method of organic triplet photosensitive agent
  • Organic triplet photosensitive agent with host-guest recognition group and preparation method of organic triplet photosensitive agent

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Experimental program
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Embodiment 1

[0070] The preparation method of the organic triplet photosensitizer with host-guest recognition group of this embodiment includes:

[0071] (1) Preparation of compound F:

[0072] Synthetic route such as figure 1 Shown.

[0073] (11) Compound B is synthesized using compound A and 1,2-dibromoethane. The specific process is as follows:

[0074] Hydroxybenzaldehyde was dissolved in ethanol, and then 1,2-dibromoethane and potassium carbonate were added to react at 78°C for 8 hours. After confirming the completion of the reaction by thin-layer chromatography, it was filtered and purified to obtain compound B; The molar ratio of hydroxybenzaldehyde, 1,2-dibromoethane and potassium carbonate is 1:5:1, and the developing agent used in thin-layer chromatography is dichloromethane. The specific purification process in this step is: extract the reaction product with dichloromethane, combine the organic phases, and use anhydrous Na 2 SO 4 After drying and using a rotary evaporator to remove th...

Embodiment 2

[0103] The difference between this embodiment and embodiment 1 is that the reaction conditions of each step are slightly different, and the details are as follows:

[0104] The preparation method of the organic triplet photosensitizer with host-guest recognition group of this embodiment includes:

[0105] (1) Preparation of compound F:

[0106] (11) Compound B is synthesized using compound A and 1,2-dibromoethane. The specific process is as follows:

[0107] Hydroxybenzaldehyde was dissolved in ethanol, and then 1,2-dibromoethane and potassium carbonate were added to react at 75°C for 7.5 hours. After confirming the completion of the reaction by thin layer chromatography, it was filtered and purified to obtain compound B; The molar ratio of hydroxybenzaldehyde, 1,2-dibromoethane and potassium carbonate is 1:4.8:1, and the developing agent used in thin layer chromatography is dichloromethane.

[0108] (12) The compound B is reacted with 2,4-dimethylpyrrole and trifluoroacetic acid in a...

Embodiment 3

[0126] The difference between this embodiment and embodiment 1 is that the reaction conditions of each step are slightly different, and the details are as follows:

[0127] The preparation method of the organic triplet photosensitizer with host-guest recognition group of this embodiment includes:

[0128] (1) Preparation of compound F:

[0129] (11) Compound B is synthesized using compound A and 1,2-dibromoethane. The specific process is as follows:

[0130] Dissolve hydroxybenzaldehyde in ethanol, then add 1,2-dibromoethane and potassium carbonate to react at 80°C for 8.5h. After confirming that the reaction is complete by thin-layer chromatography with dichloromethane, filter and purify to obtain the compound B; Among them, the molar ratio of hydroxybenzaldehyde, 1,2-dibromoethane and potassium carbonate is 1:5.5:1.2, and the developing agent used in thin layer chromatography is dichloromethane.

[0131] (12) The compound B is reacted with 2,4-dimethylpyrrole and trifluoroacetic aci...

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Abstract

The invention discloses an organic triplet photosensitive agent with a host-guest recognition group and a preparation method of the organic triplet photosensitive agent, which belong to the technicalfield of the synthesis of photosensitive agents. Hexanediamine is introduced on a meso-position benzene ring position of Bodipy in a C60-Bodipy binary compound organic triplet photosensitive agent tobe used as a supermolecule combination site, the triplet photosensitive agent with a hyperon combination site and a supermolecule main body with a triplet receptor are self-assembled in a solution, and a space distance between the triplet photosensitive agent and the triplet receptor is shortened to a molecular dimensional range, so that the triplet photosensitive agent can transfer the energy without being dispersed in an effective service life range, the non-radiation deactivation probability of a triplet exciton can be reduced, the energy transfer efficiency between the photosensitive agentand the receptor can be increased, and the upconversion efficiency can be increased.

Description

Technical field [0001] The invention relates to the technical field of photosensitizers, in particular to an organic triplet photosensitizer with a host-guest recognition group and a preparation method thereof. Background technique [0002] With the rapid development of society, the world-wide energy scarcity era has quietly come, and the environmental problems caused by the massive use of fossil fuels drive people to pay more and more attention to solar energy, an inexhaustible, safe and environmentally friendly energy source. Improving the utilization efficiency of solar energy is the unremitting pursuit of scientists in various disciplines. [0003] Up-conversion technology is a technology that can convert low-energy photons into high-energy photons. It is of great value in the field of improving solar energy utilization efficiency. It has been widely used in photovoltaics, photocatalysis, fluorescent biological imaging and other fields. There are many ways to achieve up-conver...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1055C09K2211/1059C09K2211/1092
Inventor 伍晚花杨成范春英
Owner SICHUAN UNIV
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