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Preparation method of a class of asymmetric spirobifluorene compounds derived from the transformation of functional groups on different fluorene rings

A technology for functional group transformation and spirobifluorene, applied in the field of asymmetric spirobifluorene compounds and their preparation

Inactive Publication Date: 2014-10-29
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the application of spirobifluorene compounds to organic nonlinear materials and fluorescent probes.

Method used

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  • Preparation method of a class of asymmetric spirobifluorene compounds derived from the transformation of functional groups on different fluorene rings
  • Preparation method of a class of asymmetric spirobifluorene compounds derived from the transformation of functional groups on different fluorene rings
  • Preparation method of a class of asymmetric spirobifluorene compounds derived from the transformation of functional groups on different fluorene rings

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] The preparation of 2,7-bis(malononitrile)-2',7'-bis(triphenylamino)-9,9'-spirobifluorene comprises the following steps:

[0101] (1) Preparation of 4,4'-dimethylbiphenyl

[0102]

[0103] Using cheap and easy-to-obtain 4,4'-dimethylbiphenyl as raw material, under nitrogen protection, weigh 3g (125mmol) of dry magnesium powder, 0.2g (1.2mmol) of ferric chloride in 100ml of dry trichloride in turn. In the necked flask, weigh 11 g (64.3 mmol) of p-bromotoluene into a 50 ml dry constant pressure dropping funnel. Anhydrous 60 ml of tetrahydrofuran was poured into the three-necked flask and vigorously stirred at room temperature. First, 5% p-bromotoluene was added dropwise rapidly, and after the reaction was initiated, it was slowly added dropwise. After the dropwise addition was completed, the reaction was continued for 30 min, the reaction was stopped, cooled to room temperature, and suction filtered to obtain a black filtrate, and the solvent was removed to obtain a b...

Embodiment 2

[0123] Determination of Photoluminescence Spectra of Asymmetric Spirobifluorene Compounds Derived from Functional Group Transformation on Different Fluorene Rings (2,7-bis(malononitrile)-2',7'-bis(triphenylamino)-9 ,9'-spirobifluorene as an example)

[0124] The product was formulated into 1 × 10 in solvents of different polarities -5 The solution of M was measured by absorption and emission spectra in UV-Vis spectrometer and fluorescence spectrometer, respectively. The UV absorption spectrum is attached figure 2, Fluorescence emission spectrum is attached image 3 . from In Figure 2 It can be clearly seen that the maximum absorption spectrum of the compound is around 380 nm and ends at 440 nm, which fully meets the requirements of the transparency of nonlinear materials. from image 3 It can be clearly seen that the maximum emission spectrum of the compound is around 450 nm, and the maximum emission peak is red-shifted with the increase of solvent polarity. This indi...

Embodiment 3

[0126] Test of second-order nonlinear properties of asymmetric spirobifluorene compounds derived from functional group transformation on different fluorene rings (2,7-bis(malononitrile)-2',7'-bis(triphenylamino)- 9,9'-spirobifluorene as an example)

[0127]Using the lyochromic method, acetonitrile (37.5D) and toluene (2.4D), which have a large difference in dielectric constant, are used as solvents, and the relevant data are measured and entered into the lysochromic equation, and the 2,7-bis(propanediol) is calculated. nitrile)-2',7'-bis(triphenylamino)-9,9'-spirobifluorene β CT μ g is 2344.5. Furthermore, the melting point of 2,7-bis(malononitrile)-2',7'-bis(triphenylamino)-9,9'-spirobifluorene is 177 to 181°C. It can be seen that the "up-down" asymmetric spirobifluorene compound with D-π-A structure has a large second-order nonlinear polarizability, and has very good light transmittance and thermal stability. Solve the current second-order nonlinear material "nonlinearit...

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Abstract

The invention relates to asymmetric spirobifluorene compounds derived from functional group conversion on different fluorene rings. The products of the invention have a structural formula of (I), wherein R1 and R2 are various electron-withdrawing or electron-donating groups such as various alkanes, substituted aryl, substituted heterocyclic radical, substituted alkylene, substituted amino, chlorine, bromine, and iodine, and R1 is different from R2. Cheap and easily available 4,4'-dimethyl biphenyl is used as a raw material, and the compound (I) is obtained by steps of bromination, reaction with 2,7-diX fluorenone through, and respective conversion of methyls and X groups on different fluorene rings into various functional groups. The asymmetric spirobifluorene compounds derived from functional group conversion on different fluorene rings of the invention is low in product cost, simple in synthetic route, high in yield, and easy for industrial production; the compounds have special spiro-conjugated effect, good dissolvability and high heat stability, is widely applicable to fields of organic light-emitting display, organic non-linear materials, fluorescent probes, and the like.

Description

technical field [0001] The present invention relates to a class of spirobifluorene compounds, in particular to a class of asymmetric spirobifluorene compounds derived from the transformation of functional groups on different fluorene rings, and a preparation method and application thereof. Background technique [0002] Clarkson and Gomberg et al. synthesized 9,9'-spirobifluorene as early as 1930. In 1997, Salbeck et al. used spirobifluorene in electroluminescent materials, which led to the extensive research of spirobifluorene in the field of organic optoelectronic functional materials. Due to the three-dimensional orthogonal spatial structure of spirobifluorene, the close packing of chromophores in the molecule can be avoided, and the thermal stability and solubility of the material can be improved; 3 Hybrid spiro carbon atoms can control the length of molecular conjugation or produce special spiro conjugation effects. In recent years, spirobifluorene has become a "star m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/42C07C253/30C09K11/06H01L51/54G02F1/361
Inventor 肖海波殷鸿尧张晓瑛丁磊郭松魁
Owner SHANGHAI NORMAL UNIVERSITY
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