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Application of triphenylamine modified binaphthalene derivative

A technology of binaphthyl derivatives and triphenylamine, which is applied in the field of triphenylamine modified binaphthyl derivatives, and can solve the problems of spectral changes, detection of iron ions without relevant research, etc.

Active Publication Date: 2020-04-10
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, 7,7′-bis(4-diphenylamino-phenyl)-1,1′-binaphthol can selectively detect fluoride ions based on hydrogen bonding, resulting in spectral changes
However, TPA-bonded BINAP-type probes have not been studied for the detection of iron ions.

Method used

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  • Application of triphenylamine modified binaphthalene derivative
  • Application of triphenylamine modified binaphthalene derivative
  • Application of triphenylamine modified binaphthalene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The preparation of embodiment 1 compound

[0052] (1) Synthesis of Compound 1

[0053] The synthetic route of compound 1 is as follows:

[0054]

[0055] The specific synthetic steps of compound 1 are as follows:

[0056] In a 250mL round bottom flask, add 6-bromo-2-naphthol (5g, 22.4mmol), FeCl 3 ·6H 2 O (12.1 g, 44.8 mmol) and distilled water (100 mL). After stirring the reaction at 60 °C for 24 h, it was cooled to room temperature. Dichloromethane (DCM) was added to the reaction liquid, fully dissolved and extracted and separated to obtain an organic phase. The obtained organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, and distill under reduced pressure to obtain the crude product. The crude product was further purified by silica gel column chromatography. The eluent system was n-hexane and ethyl acetate (6:1) to obtain a white solid with a yield of 74.3% (3.7 g, 8.3 mmol).

[0057] The obtained white solid was characterized by a nuclear magn...

Embodiment 2

[0093] Embodiment 2 Iron ion titration experiment and detection limit calculation

[0094] Prepare 250mL 2×10 with a volumetric flask -5 The THF solution of M probe, take 10mL solution accurately with a pipette each time, add 20uL 0-40equiv of FeCl during stirring 3 aqueous solution, continue to stir for 3min to make the probe and Fe 3+ After sufficient exposure, measure the fluorescence emission spectrum of the corresponding solution.

[0095] Such as Figure 15 As shown, adding Fe 3+ It can weaken the fluorescence intensity until the fluorescence is quenched, and different Fe can be observed with the naked eye under a 365nm ultraviolet lamp 3+ Fluorescence response of the probe solution with different concentration, and take pictures and record in time. Among them, in the THF solution of 6,6-TB-1, with the addition of Fe 3+ The fluorescence intensity decreased sharply with a slight red shift as the amount increased from 0 to 40 equiv. while for 7,7-OMeTB-1, 15 equival...

Embodiment 3

[0097] Embodiment 3 selectivity test experiment

[0098] To evaluate the selectivity of the probe, we tested the fluorescence response of the probe with various metal ions. Prepare 250mL 2×10 with a volumetric flask -5 For the THF solution of the M probe, accurately take 10 mL of the solution with a pipette each time, and add 15 equivalents or 40 equivalents of different metal ions (Fe 3+ , K + , Mg 2+ , Na + , Ni 2+ ,Co 2+ , Ca 2+ , Al 3+ , Ba 2+ , Mn 2+ , Cr 3+ , Cu 2 + , Cd 2+ , Pd 2+ and Zn 2+ ), and measure the fluorescence emission spectrum of the corresponding solution after fully stirring. Under the 365nm ultraviolet lamp, observe and take pictures in time to record the fluorescence response ( Figure 17 ). In order to more intuitively observe the effects of various metal ions on the fluorescence intensity of the solution, we use F / F 0 is the ordinate (F is the fluorescence intensity of the solution after adding each metal ion, F 0 For the fluoresce...

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Abstract

The invention discloses an application of a triphenylamine modified binaphthalene derivative. The compound capable of emitting fluorescence can be selectively combined with iron ions (Fe<3+>) at a single point to cause fluorescence quenching, so that the compound can be used as a fluorescent probe for detecting Fe<3+>, and the probe has the characteristics of high sensitivity and interference resistance and is easy to synthesize.

Description

technical field [0001] The invention relates to the use of a triphenylamine-modified binaphthyl derivative. Background technique [0002] Fluorescent probes for a large number of ions and neutral analytes have become powerful tools for environmental monitoring, biological research, and disease diagnosis due to their high sensitivity, good selectivity, fast response, simple synthesis, and convenient operation. In the past two decades, various fluorophores have been used as the signal source of fluorescent chemical sensors, according to the reaction mechanism and host-guest interaction, fluorescent probes have been developed rapidly. From the perspective of photophysics, analyte detection with fluorescent chemical sensors usually involves chelation-induced enhanced fluorescence (CHEF), intramolecular charge transfer (ICT), photo-induced electron transfer (PET), aggregation-induced emission (AIE), etc. to realise. [0003] Iron ions (Fe 3+ ) are abundant elements and essent...

Claims

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Application Information

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IPC IPC(8): C09K11/06G01N21/64
CPCC09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1088G01N21/6428G01N2021/6432
Inventor 田梅张宏黄巧茜雷鸣
Owner ZHEJIANG UNIV
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