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A triplet photosensitizer, its preparation method and an upconversion system

A photosensitizer, triplet technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of low up-conversion luminous efficiency, difficult to achieve natural visible light applications, etc., and achieve the effect of strong absorption

Active Publication Date: 2019-02-22
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] After investigation and research, it is found that most of the current photosensitizer molecules need high-power excitation light in the process of TTA up-conversion, but they obtain low up-conversion luminous efficiency, and it is difficult to realize the application of natural visible light.

Method used

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  • A triplet photosensitizer, its preparation method and an upconversion system
  • A triplet photosensitizer, its preparation method and an upconversion system
  • A triplet photosensitizer, its preparation method and an upconversion system

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preparation example Construction

[0033] The present invention also provides a kind of preparation method of above-mentioned photosensitizer, comprises the following steps:

[0034] Have the compound of structure shown in formula (I) and I 2 and HIO 3 An iodination reaction occurs to obtain a photosensitizer having a structure shown in formula (BDP-1) to formula (BDP-3);

[0035]

[0036] Specifically, under protective atmosphere conditions, the compound having the structure shown in formula (I), elemental iodine and a saturated solution of iodic acid are mixed and heated for reaction to obtain a reaction product;

[0037] The reaction product is purified to obtain photosensitizers having structures represented by formula (BDP-1) to formula (BDP-3).

[0038] Wherein, the BDP-1 protective atmosphere condition is preferably nitrogen, and the molar ratio of the compound having the structure represented by formula (I) to iodine is 1:5-1:10. The reaction temperature is 30-40 degrees Celsius, and the reaction ...

Embodiment 1

[0077] Prepare the compound with structure shown in formula (II) by p-hydroxybenzaldehyde and n-bromobutane

[0078] P-Hydroxybenzaldehyde (2.44g, 20mmol), potassium carbonate (4.15g, 30mmol) were dissolved in 50ml of DMF solution. After heating to reflux for 1 h, the temperature was lowered to 35° C., n-bromobutane (20 mmol, 2.72 g) was slowly added, and after stirring for 10 min, the temperature was raised to reflux for 12 h. After cooling to room temperature, the solvent was removed by rotary evaporation, extracted with dichloromethane and water, dried over anhydrous sodium sulfate, the solvent was removed by rotary evaporation, and purified by petroleum ether and ethyl acetate (volume ratio: 1:1). 3.04 g of yellow oily liquid, that is, the compound having the structure shown in formula (II). The yield was determined to be 85.4%.

[0079]

[0080] NMR data: 1 H NMR (400MHz, CDCl 3 )δ9.88(s,1H),7.82(d,J=8.0Hz,2H),6.99(d,J=8.0Hz,2H),4.05(s,2H),1.88–1.73(m,2H), 1.52(t,...

Embodiment 2

[0082] Prepare the compound (BDP) with the structure shown in the formula (I) by the compound with the structure shown in the formula (II) and pyrrole

[0083] A compound (8.43mmol, 1.5g) having a structure shown in formula (II) was dissolved in 150ml of dry dichloromethane, and under nitrogen protection, pyrrole (1.13g, 16.86mmol, 1.18ml) and 0.15ml of trifluoro Acetic acid catalyst, at room temperature (after adding trifluoroacetic acid, the color gradually deepens, and after half an hour, the solution turns black.) After reacting for 10 hours, add DDQ (8.43mmol, 1.91g), react for 1 hour, and then cool with ice water, Add triethylamine (10equiv, 11.6ml), react for 30min, and then add boron trifluoride ether (11.6ml). The reaction was stopped after 30 min of reaction. Remove the solvent by rotary evaporation, add a large amount of water to remove triethylamine and boron trifluoride ether, then add dichloromethane and water to extract, dry with anhydrous sodium sulfate, and t...

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Abstract

The invention provides a photosensitizer having a structure shown as a formula (BDP-1) to a formula (BDP-3). The photosensitizer provided by the invention is a triplet state photosensitizer; the photosensitizer has a high mole extinction coefficient at visible light, and emits high-strength light in TTA up-conversion, i.e., efficient up-conversion is realized under the condition of a low-power (5.0mw) excitation light source; in addition, strong absorption on the visible light can be realized, up-conversion from green light to blue light and that from red light to the green light are realizedby a triplet state-triplet state annihilation process, and the photosensitizer having the property can be widely applied to fields such as photocatalytic organic synthesis, photodynamic treatment, bioimaging and solar cells.

Description

technical field [0001] The invention belongs to the technical field of photon upconversion, and in particular relates to a triplet photosensitizer and its application in triplet annihilation upconversion. Background technique [0002] Photon up-conversion is a special technology that can convert low-energy long-wavelength photons into high-energy short-wavelength photons. That is, the anti-Stokes shift luminescence can be realized. This performance makes it widely used in photocatalytic organic synthesis, photodynamic therapy, bioimaging and solar cells. [0003] At present, there are three main technologies used for upconversion: one is rare earth material upconversion, the other is two-photon absorption upconversion, and the third is triplet-triplet annihilation upconversion (TTA-UC). Among these three technologies, the first two The required excitation light energy is high. Relatively speaking, triplet-triplet annihilation upconversion requires low excitation light int...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06
Inventor 籍少敏梁辉霍延平董方帝李宗值余梓东
Owner GUANGDONG UNIV OF TECH
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