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Fluorene derivatives with AIE properties, preparation method and application

A technology of fluorene derivatives and aromatic hydrocarbon derivatives, which is applied in the field of aggregation-induced emission (AIE) materials, and can solve problems such as long measurement time

Active Publication Date: 2022-06-10
LIAONING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, existing methods often require specialized and expensive laboratory equipment and long measurement times
Although the detection of fluorescent probes has the advantages of relatively simple, low cost, short response time, high sensitivity and strong specificity, because tryptophan is a small biological molecule, no AIE-type fluorescent probes have been used to detect it so far. Related reports

Method used

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  • Fluorene derivatives with AIE properties, preparation method and application
  • Fluorene derivatives with AIE properties, preparation method and application
  • Fluorene derivatives with AIE properties, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0025] The preparation method of the fluorene derivatives with AIE characteristics of the present invention is carried out in accordance with the following steps:

[0026] Step 1: First add 5.0g fluorene and 150 mL chloroform into the bottle, then add 75 mg anhydrous ferric chloride to the bottle, stir and cool to 0°C in an ice-water bath, then add 1.6 mL liquid bromine dropwise to the bottle, pipette Remove from the ice-water bath and continue to stir for 3 hours, then add 100 mL of saturated sodium thiosulfate solution dropwise to the reaction system until the red color disappears completely, then separate the whole, extract the organic phase with dichloromethane 3-4 times, anhydrous MgSO 4 After drying, after rotary evaporation under reduced pressure, a yellow solid was obtained, which was dissolved in 80 mL of absolute ethanol, and crystals were precipitated by cooling to obtain 2-bromofluorene;

[0027] Step 2: Put 7.5 g of 2-bromofluorene, 30 mL of dimethyl sulfoxide and...

Embodiment 4

[0040] Embodiment 4: The compound is used as the competition experiment of fluorescent probe to amino acid

[0041] In order to determine whether the compound specifically recognizes tryptophan, leucine (Leu), serine (Ser), methionine (Met), alanine (Ala), and isoleucine (Ile) were studied respectively. , threonine (Thr), proline (Pro), arginine (Arg), lysine (Lys), aspartic acid (Asp), glutamic acid (Glu), tyrosine (Tyr) , phenylalanine (Phe), valine (Val), cysteine ​​(Cys), histidine (His), glycine (Gly) and tryptophan (Trp) in the presence of the above amino acids Spectrum, such as Image 6 shown.

[0042] The results show that: in the presence of Trp, the emission intensity of the mixture is enhanced, while there is almost no change in the emission peak intensity in the absence of Trp, only other amino acids. It shows that even in the presence of other amino acids, the fluorescence intensity of the compound is also significantly increased under the addition of Trp, indi...

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PUM

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Abstract

The invention discloses a fluorene derivative with AIE characteristics, the structural formula is as follows: said R=-CHO, -COOH, -Br, -I, -NO 2 ,-NH 2 ,-OCH 3 ,-CH 3 , -CN, -NHCOCH 3 ,-CF 3 or-CCl 3 , can be used as a fluorescent probe to identify small biological molecules, not only has efficient and specific recognition of tryptophan (the detection limit is 1.15μM), but also can be used to detect explosives, anions, metal cations (including rare earth metals), etc. Small molecular substances.

Description

technical field [0001] The invention relates to an aggregation-induced emission (AIE) material, in particular to a fluorene derivative with AIE characteristics, a preparation method and an application. Background technique [0002] Aggregation-induced emission (AIE) materials exhibit weak emission or even non-emission when dissolved, but exhibit strong emission in the aggregated or solid state. Most traditional AIE molecules are based on hexaphenylsilole (HPS), tetraphenylethylene (TPE) or distyryl anthracene (DSA), but the synthesis process of HPS and its derivatives is cumbersome, TPE, DSA and their Derivatives have potential photobleaching and photooxidation effects. Fluorescent probes can specifically bind to target molecules or ions, and cause the fluorescent signal of the reaction system to change after action. At present, there have been related reports on the use of aggregation-induced emission (AIE) materials as fluorescent probes, but they are often used in the d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C25/22C07C22/06C07C22/08C07C17/263C07C1/32C07C13/567C07C41/30C07C43/21C07C45/68C07C47/546C07C51/353C07C63/49C07C201/12C07C205/06C07C209/68C07C211/45C07C231/12C07C233/07C07C253/30C07C255/50C09K11/06G01N21/64
CPCC07C25/22C07C22/06C07C22/08C07C13/567C07C43/21C07C47/546C07C63/49C07C205/06C07C211/45C07C233/07C07C255/50C09K11/06G01N21/6428G01N2021/6439C07C2603/18C09K2211/1007C09K2211/1011
Inventor 闫杰黄欣桐韩莹莹田昕王嘉琪
Owner LIAONING NORMAL UNIVERSITY
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