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Quinoline-substituted anhydride naphthalene derivative, iridium complex thereof and application in pH (potential of hydrogen) sensing

A technology of iridium complexes and derivatives, applied in the field of sensors, can solve the problems of single emission color change, narrow pH value detection range, inaccurate pH value, etc., and achieve the effects of fast response speed, high sensitivity and simple preparation.

Inactive Publication Date: 2012-09-12
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, pH sensors based on fluorescent small molecules and heavy metal iridium complexes have been widely studied, but there are still related problems. For example, the complexes are difficult to be completely water-soluble, making the measured pH value not very accurate, and the pH It is worth noting that the detection range is too narrow and the color change of the luminescence is too single, which increases the difficulty of marketization

Method used

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  • Quinoline-substituted anhydride naphthalene derivative, iridium complex thereof and application in pH (potential of hydrogen) sensing
  • Quinoline-substituted anhydride naphthalene derivative, iridium complex thereof and application in pH (potential of hydrogen) sensing
  • Quinoline-substituted anhydride naphthalene derivative, iridium complex thereof and application in pH (potential of hydrogen) sensing

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Effect test

Embodiment 1

[0045] Example 1: Preparation of 6-(4-phenyl-quinolin-2-yl)-benzo[de]isochromene-1,3-diketone (PQBD)

[0046] Dissolve 2.62 g (20 mmol) of aluminum trichloride into 20 mL of DCM, add 1.54 g (10 mmol) of acenaphthylene after the complete dissolution of aluminum trichloride, then add 2 mL of acetic anhydride, and stir the solution at room temperature for 3 hours , then poured into a large amount of water, stirred until the color of the solution turned pale yellow, then extracted with DCM, dried with anhydrous magnesium sulfate and concentrated, and used PE:EA (20:1, v:v) as the eluent column Chromatographic separation gave a yellow product, which was finally recrystallized from ethanol to give 0.137 g of light yellow crystal 1-acenaphthyl-5-ylethanone. Yield: 70%. 1 H NMR (CDCl 3 , 400 MHz) δ (ppm): 8.74-8.72 (d, 1H), 8.08-8.07 (d, 1H), 7.62-7.58 (t, 1H), 7.38-7.36 (d, 1H), 7.31-7.30 (d , 1H), 3.36-3.35 (m, 4H), 2.56-2.55 (m, 3H). GC-MS (m / z): 196.

[0047] Take 0.1 g (0...

Embodiment 2

[0050] Embodiment 2: Complex (PQBD) 2 Preparation of Ir(pic)

[0051] Weigh IrCl 3 ·3H 2 O (0.352 g, 1 mmol) was added to a three-necked flask, vacuum-filled with nitrogen-vacuumized on the double-row tube, and cycled three times, and finally the reaction system was protected with nitrogen. 6-(4-Phenyl-quinolin-2-yl)-benzo[de]isochromene-1,3-dione (PQBD) (1.001 g, 2.5 mmol), poured into water (3 mL, 165 mmol) Add ethylene glycol ether (9mL, 93mmol) into the reaction system, stir, and raise the temperature of the reaction system to 120°C. The reaction time is 24 hours, and a reddish-brown precipitate is formed during the reaction. The reaction system was cooled to room temperature, and then the precipitate was filtered and washed with water and ethanol to obtain a reddish-brown solid product, namely the iridium dichloro bridge compound of PQBD.

[0052] Weigh the iridium dichloro bridge compound (0.411g, 0.2 mmol) and Na of PQBD 2 CO 3(1.0 mmol) and added to a three-necke...

Embodiment 3

[0054] Embodiment 3: The ultraviolet absorption of PQBD and the fluorescence emission spectrometry titration experiment of PQBD when the pH value is constantly increasing:

[0055] Compound PQBD was formulated as 4 × 10 -5 mol / L of DMSO-H 2 O (1:9, v / v) solution, pipette 2.5 mL of the prepared compound PQBD solution in a fluorescence cuvette, and drop 2 μL of 1×10 -2 mol / L NaOH aqueous solution until equilibrium is reached (that is, the absorption spectrum no longer changes significantly). When no NaOH aqueous solution was added dropwise, the absorption spectrum of PQBD had a strong absorption peak at 363nm. When adding constantly with NaOH aqueous solution, when pH value constantly increases, the absorption peak at 363nm place weakens gradually, appears new absorption peak at 305nm place, and the intensity of new peak constantly increases with the increase of pH value (as in the accompanying drawing figure 1 shown). The entire absorption spectrum has a blue shift, and ...

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Abstract

The invention discloses a quinoline-substituted anhydride naphthalene derivative, an iridium complex thereof and application in pH (potential of hydrogen) sensing. A chemical structure of a fluorescence sensing chemistry device can be shown by a general formula (I) and a general formula (II), wherein each of R1 and R2 is one of hydrogen ion, halogen ion, nitryl, linear chains, branched chains or annular fat alkyl of 1 to 18 carbon ions, substituted alkyl, akloxy, alkyl sulphanyl, aryl, substituted aryl, heterocyclic aryl and substituted heterocyclic aryl. By a traditional method for preparing the iridium complex, the iridium complex based on the quinoline-substituted anhydride naphthalene derivative is obtained by means of coordination and showed in the formula (II). A pH sensor for fluorescence and phosphorescence detects pH values by color change of solution, change of ultraviolet visual absorption spectra and change of fluorescence transmitting spectra.

Description

technical field [0001] The invention relates to a fluorescent and phosphorescent pH sensor, which belongs to the technical field of sensors. Specifically, it relates to a class of quinoline substituted naphthalene anhydride derivatives and their iridium complexes and their application in pH sensors. Background technique [0002] Nowadays, due to the very important role of pH in the environment, daily life and human body, for example, some enzymes can only show catalytic functions at certain pH values, and real-time detection of pH has become a research hotspot. Some small organic molecules that respond to pH have been reported[1-3]. Compared with small organic molecules, pH sensors based on heavy metal iridium complexes have longer phosphorescence lifetimes, large Stoke shifts, and easy resolution of excitation and emission. etc., and the iridium complex has a certain water solubility, which is very important for detecting the pH value of the system. At present, the chemi...

Claims

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Application Information

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IPC IPC(8): C07D405/04C07F15/00G01N21/25G01N21/31G01N21/33G01N21/64
Inventor 梅群波蒋渊知黄维童碧海郭远辉翁洁娜张彬
Owner NANJING UNIV OF POSTS & TELECOMM
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