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Double-state luminous porphyrin fluorescent material and preparation method thereof

A technology of fluorescent materials and porphyrins, which can be used in luminescent materials, chemical instruments and methods, photovoltaic power generation, etc.

Active Publication Date: 2021-09-14
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, like most organic fluorescent small molecules, even though they exhibit strong fluorescence emission in the solution state, they exhibit non-fluorescence or very weak fluorescence in the solid state, because porphyrins tend to pass through hydrogen bonds, van der Waals Driving forces such as interactions, electrostatic interactions, and hydrophobic effects form π-π stacking aggregates, leading to ACQ
Although porphyrins have been widely used in tumor fluorescence detection and imaging-guided cancer diagnosis and treatment, the ACQ effect limits their maximum fluorescence imaging capabilities

Method used

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  • Double-state luminous porphyrin fluorescent material and preparation method thereof
  • Double-state luminous porphyrin fluorescent material and preparation method thereof
  • Double-state luminous porphyrin fluorescent material and preparation method thereof

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Embodiment 1

[0093] Embodiment 1 A kind of preparation method of the porphyrin fluorescent material of double state light emission

[0094] This embodiment includes the following steps carried out in sequence:

[0095] S1. get 16mmol of 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin and 24mmol of hexamethylenetetramine, dissolve in 100mL of trifluoroacetic acid under the protection of nitrogen, Reflux reaction at 70°C for 20h, add 100mL of hydrochloric acid with a concentration of 1mol / L after the reaction, stir at 25°C for 2h, adjust the reaction solution to neutral with NaOH solution, extract with dichloromethane and take the organic layer, The organic layer was washed 3 times with saturated brine, then washed with anhydrous Na 2 SO 4 Dry, filter, remove the solvent by rotary evaporation under reduced pressure, then use a solution of petroleum ether and dichloromethane mixed at a volume ratio of 3:1 as the eluent for elution, then use a silica gel column to purify the product, and fin...

Embodiment 2

[0104] Embodiment 2 A kind of preparation method of the porphyrin fluorescent material of double state light emission

[0105] This embodiment includes the following steps carried out in sequence:

[0106] S1. get 16mmol of 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin and 16mmol of hexamethylenetetramine, dissolve in 100mL of trifluoroacetic acid under the protection of nitrogen, Reflux reaction at 90°C for 10h, add 100mL hydrochloric acid with a concentration of 0.8mol / L after the reaction, stir at 30°C for 3h, adjust the reaction solution to neutral with KOH solution, extract with dichloromethane and take the organic layer , the organic layer was washed 5 times with saturated brine, and washed with anhydrous Na 2 SO 4 Dry, filter to remove the desiccant, remove the solvent by rotary evaporation under reduced pressure, then use a solution of petroleum ether and dichloromethane mixed in a volume ratio of 3:1 as the eluent for elution, and then use a silica gel column to p...

Embodiment 3

[0109] Embodiment 3 A kind of preparation method of the porphyrin fluorescent material of double state light emission

[0110] This embodiment includes the following steps carried out in sequence:

[0111] S1. get 16mmol of 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin and 32mmol of hexamethylenetetramine, dissolve in 100mL of trifluoroacetic acid under the protection of nitrogen, Reflux reaction at 80°C for 12 hours, add 100mL of hydrochloric acid with a concentration of 1.5mol / L after the reaction, stir at 20°C for 3h, adjust the reaction solution to neutral with NaOH solution, extract with dichloromethane and take the organic layer , the organic layer was washed 4 times with saturated brine, and washed with anhydrous Na 2 SO 4 Dry, filter to remove the desiccant, remove the solvent by rotary evaporation under reduced pressure, then use a solution of petroleum ether and dichloromethane mixed in a volume ratio of 3:1 as the eluent for elution, and then use a silica gel co...

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Abstract

The invention discloses a double-state luminous porphyrin fluorescent material which is obtained by taking porphyrin as a basic fluorophore and carrying out structural modification through a chemical method. The invention also discloses a preparation method of the double-state luminous porphyrin fluorescent material, wherein the preparation method comprises the steps: modifying 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin through a Duff hydroformylation reaction, and then carrying out a Schiff base reaction on the modified 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin and a symmetric diamino compound to prepare the double-state luminous porphyrin fluorescent material. According to the prepared double-state luminous porphyrin fluorescent material, the formation of pi-pi stacked aggregates can be effectively inhibited or weakened through a specific space structure, and due to the improvement of the aggregation state, the porphyrin fluorescent material not only can emit red fluorescence in a solution, but also has the characteristic of red fluorescence emission in a solid state. The preparation method can be widely applied to preparation of the double-state luminous porphyrin fluorescent material.

Description

technical field [0001] The invention belongs to the technical field of organic materials, and relates to a high-efficiency luminescent organic fluorescent material, in particular to a double-state luminescent porphyrin fluorescent material and a preparation method thereof. Background technique [0002] Organic small molecule optical functional materials have always been the research hotspot and direction of organic chemistry researchers. They have broad applications in many fields such as cell imaging, organic light-emitting diodes, and chemical sensing. Organic small molecules with excellent optical properties are these Materials fulfill the core of their applications. Traditional organic light-emitting materials are prone to aggregation-induced fluorescence quenching (ACQ), which emits weak or no light at high concentrations and in the aggregated state. However, aggregation-induced emission (AIE) materials, which have been developed rapidly in the past two decades, only em...

Claims

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Application Information

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IPC IPC(8): C07D519/00C09K11/06
CPCC07D519/00C09K11/06C09K2211/1074Y02E10/549
Inventor 曾荣今邹柔张培盛喻优成奋民陈述张崇华陈建
Owner HUNAN UNIV OF SCI & TECH