Novel spirobifluorene compound 2-methyl-7-benzimidazolyl spirobifluorene, and method and application thereof

A technology of benzimidazolylspiro and dimethylspirobifluorene, which is applied in the field of new spirobifluorene compounds and their preparation, and achieves the effects of wide detection range, high fluorescence intensity and high thermal stability

Inactive Publication Date: 2012-09-12
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the current research on pH fluorescent probes is limited to the effective detection of pH value under single acidic or alkaline conditions (Francisco Galindo, M.Isabel Burguete, Laura Vigara, Santiago V.Luis, Nurul Kabir, Jelena Gavrilovic, and David A. Russell, Angew. Chem. Int. Ed. 2005, 44, 6504–6508)

Method used

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  • Novel spirobifluorene compound 2-methyl-7-benzimidazolyl spirobifluorene, and method and application thereof
  • Novel spirobifluorene compound 2-methyl-7-benzimidazolyl spirobifluorene, and method and application thereof
  • Novel spirobifluorene compound 2-methyl-7-benzimidazolyl spirobifluorene, and method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] 1) Synthesis of 4,4'-dimethylbiphenyl

[0054] Under nitrogen protection, weigh 3g (125mmol) dry magnesium powder, 0.2g (1.2mmol) ferric chloride in a 100mL dry three-necked flask, then weigh 11g (64.3mmol) p-bromotoluene in 50mL and dry in a constant pressure dropping funnel. Inject 60 mL of anhydrous THF into the three-necked flask, and vigorously stir at room temperature. First quickly add 5% p-bromotoluene dropwise, and then slowly add dropwise after the reaction is triggered. After the dropwise addition was completed, the reaction was continued for 30 min, the reaction was stopped, cooled to room temperature, and filtered with suction to obtain a black filtrate, and the solvent was removed to obtain a black paste. Add 50mL of dichloromethane and 30mL of water in sequence, vibrate vigorously, and a large number of flocs appear in the solution. Slowly add dilute hydrochloric acid solution dropwise to the solution and shake continuously until the flocs disappear. ...

Embodiment 2

[0065] Example 2: Response of Compound Fluorescence Spectrum to pH

[0066] Compound (I) was formulated as 1 × 10 -5 M, the solvent is acetonitrile: water = 15:1, the pH is adjusted with different concentrations of NaOH and HCl solutions, and the fluorescence spectra at different pHs are tested. The test conditions are: the excitation wavelength is 338nm, the slit width is 5 / 5, and the voltage is 420V. Test results such as image 3 and Figure 4 .

[0067] from image 3 It can be clearly seen that the fluorescence emission peak of the compound red shifts continuously with the decrease of pH, and the maximum emission intensity also decreases continuously. The intensity of its maximum emission peak decreased from 900 to 530, and at the same time, the maximum emission peak was red-shifted from 380nm to 418nm, a red-shift of 38nm. The peak shape of the fluorescence spectrum also gradually changed from a more obvious triplet peak at neutral to a singlet peak. And throughout ...

Embodiment 3

[0069] Example 3: Response of Compound Absorption Spectrum to pH

[0070] Compound (I) was formulated as 1 × 10 -5 M, the solvent is acetonitrile: water = 15:1 (volume ratio), the pH is adjusted with different concentrations of NaOH and HCl solutions, and the absorption spectra at different pHs are tested. Test results such as Figure 5 and Image 6 .

[0071] from Figure 5 It can be seen that the influence of pH on the absorption spectrum of the compound is obvious. In a neutral environment, it can be clearly seen that it has two absorption spectra, which are 335nm and 352nm. When the environment becomes acidic, they red shift to 347nm and 365nm, respectively. Moreover, the second absorption peak becomes smoother, and two isotopes appear at 340nm and 352nm during the whole change process.

[0072] from Image 6 It can be seen that the influence of pH on the absorption spectrum of the compound is obvious. In a neutral environment, it can be clearly seen that it has t...

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Abstract

The invention discloses novel spirobifluorene compound 2-methyl-7-benzimidazolyl spirobifluorene. The method for preparing the novel spirobifluorene compound comprises the following steps of performing coupling reaction on parabromotoluene serving as a raw material, and performing bromination, grignard reaction, dehydration cyclization and oxidizing reaction to obtain the 2-methyl-7-formacyl spirobifluorene, and reacting the 2-methyl-7-formacyl spirobifluorene with o-phenylendiamine to obtain the compound (I). The method and the compound have the advantages that raw materials are low in price and readily-available, the synthetic route is simple, the yield is high, and the method can be applied to large-scale production; because a three-dimensional rigid structure of spirobifluorene is adopted, the compound has a high yield of fluorescent quantum and fluorescence intensity; the compound has high thermal stability and high solubility; the compound can be applied to the field of electroluminescence, and when the compound is used as a luminescent layer to prepare an electroluminescent device, pure white light can be obtained; and when the compound is applied to a fluorescent ion probe, the probe has high sensitivity, can make quick response to a pH value of a solution, is a pH probe with a quite wide response range and has quite good application prospect.

Description

technical field [0001] The invention relates to the fields of electroluminescence and fluorescent probes, in particular a novel spirobifluorene compound capable of emitting white light in an electroluminescence device and used for pH detection and a preparation method thereof. Background technique [0002] Organic Light Emitting Diode (OLED) has become a promising flat panel display device due to its advantages of low energy consumption, fast response, light weight and rich colors. Usually organic light-emitting materials mainly emit monochromatic light such as red, green, and blue. Since Kido J et al. reported White Organic Light Emitting Diode (WOLED) in 1994, it has been widely used in liquid crystal display backlights, full-body The potential application in the field of color display and lighting has become a research hotspot at home and abroad. There are many ways to obtain white light in organic electroluminescent devices. At present, the methods for obtaining white o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C09K11/06H01L51/54G01N21/64
Inventor 肖海波殷鸿尧
Owner SHANGHAI NORMAL UNIVERSITY
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