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A class of "up-down" asymmetric spirobifluorene compounds derived from methyl transformation on the fluorene ring and its preparation method and application

An asymmetric, spirobifluorene technology, applied in the field of "up-down" 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

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Problems solved by technology

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

Method used

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  • A class of "up-down" asymmetric spirobifluorene compounds derived from methyl transformation on the fluorene ring and its preparation method and application
  • A class of "up-down" asymmetric spirobifluorene compounds derived from methyl transformation on the fluorene ring and its preparation method and application
  • A class of "up-down" asymmetric spirobifluorene compounds derived from methyl transformation on the fluorene ring and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] The preparation method of 2,7-diformyl-2',7'-dibromo-9,9'-spirobifluorene comprises the following steps:

[0096] (1) Preparation of 4,4'-dimethylbiphenyl

[0097]

[0098] Using cheap and easy-to-obtain 4,4'-dimethylbiphenyl as raw material, under the protection of nitrogen, weigh 3g (125mmol) of dry magnesium powder, 0.2g (1.2mmol) of ferric trichloride in 100ml of dry tris In the flask, weigh 11g (64.3mmol) p-bromotoluene in a 50ml dry constant pressure dropping funnel. Inject 60 ml of anhydrous tetrahydrofuran into the three-necked flask, and vigorously stir at room temperature. First add 5% p-bromotoluene rapidly and dropwise after the reaction is initiated. 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, vibrat...

Embodiment 2

[0112] The preparation of 2,7-dicyano-2',7'-dicarbazole-9,9'-spirobifluorene comprises the following steps:

[0113]

[0114] Under nitrogen protection, add 10mg (0.014mmol) 2,7-diformyl-2',7'-dicarbazole-9,9'-spiro Difluorene, 20mg (0.29mmol) of hydroxylamine hydrochloride, and then inject 2ml of freshly distilled N-methylpyrrolidone (NMP), and react at 115°C for 12h. After stopping the reaction, cool to room temperature, add about 5ml of ice water, precipitate a large amount of solid, filter to obtain a yellow solid, column chromatography (petroleum ether: ethyl acetate = 15:1 as a developer), and obtain 8 mg of a light yellow solid, namely 2 , 7-dicyano-2',7'-dicarbazole-9,9'-spirobifluorene, the yield was 80%. 1 H NMR (400MHz, CDCl 3 , δppm): 6.8(s, 2H), 7.1(d, 4H), 7.2(t, 4H), 7.3(t, 4H), 7.5(s, 2H), 7.8(d, 2H), 7.9(d, 2H), 8.1(d, 4H), 8.3(d, 2H), 8.5(d, 2H)

Embodiment 3

[0116] Determination method of photoluminescence spectrum of "up-down" asymmetric spirobifluorene compound derived from methyl transformation on fluorene ring (using 2,7-dicyano-2',7'-dicarbazole-9, 9'-spirobifluorene as an example)

[0117] The product was formulated in solvents of different polarities to 1×10 -5 The solution of M was measured by absorption spectrum and emission spectrum in UV-Vis spectrometer and fluorescence spectrometer respectively. UV absorption spectrum see attached Figure 5 , the fluorescence emission spectrum is shown in the attached Image 6 . from Figure 5 It can be clearly seen that the absorption spectrum of the compound is around 325nm and cuts off at 370nm, which fully meets the practical requirements of the transparency of nonlinear materials. from Image 6 It can be clearly seen that the maximum emission spectrum of the compound is around 410nm, and the emission peak red shifts with the increase of solvent polarity. This shows that th...

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Abstract

The invention relates to a 'vertically' unsymmetrical spirobifluorene compound derived from conversion of methyl on a fluorene loop. A structural formula of the compound is (I) shown in the source text, wherein R1 and R2 in the formula can be various electron withdrawing and donating groups such as alkyl, substituted aryl, substituted heterocyclic radical, substituted alkylene, substituted amino, chlorine, bromine, iodine and the like, and the R1 and R2 are different. 4,4'-dimethyl diphenyl which is cheap and easy to obtain is used as a raw material to be bromized and reacted with fluorenone or 2,7-substituted fluorenone to covert the methyl on the fluorine loop into various fluctional groups and the like to obtain the compound (I). The 'vertically' unsymmetrical spirobifluorene compound derived from conversion of methyl on the fluorene loop is low in cost, simple in synthetic route, high in yield and easy in industrial production, has special spiral conjugation effect, high dissolubility and high heat stability, and is widely applicable to fields of organic luminous display, organic nonlinear materials, fluorescent probes and the like.

Description

technical field [0001] The invention relates to a class of spirobifluorene compounds, in particular to a class of "up-down" asymmetric spirobifluorene compounds derived from methyl transformation on a fluorene ring, and a preparation method and application thereof. Background technique [0002] As early as 1930, Clarkson and Gomberg synthesized 9,9'-spirobifluorene. In 1997, Salbeck et al. used spirobifluorene in electroluminescent materials, which triggered the extensive development of spirobifluorene in the field of organic optoelectronic functional materials. Because spirobifluorene has a three-dimensional orthogonal space structure, it can avoid the close packing of chromophores in the molecule, and improve the thermal stability and solubility of the material; and through sp 3 The hybrid spiro carbon atoms can realize the control of molecular conjugation length or produce special spiro conjugation effect. In recent years, spirobifluorene has become a "star molecule" in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/55C07C45/00C07D209/86C09K11/06H01L51/54G02F1/361
Inventor 肖海波殷鸿尧张晓瑛丁磊郭松魁
Owner SHANGHAI NORMAL UNIVERSITY
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