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Top-bottom asymmetrical tert-butyl spirobifluorene compound

A tert-butylspirobifluorene, asymmetric technology, applied in the field of "up-down" asymmetric tert-butylspirobifluorene compound and its preparation

Inactive Publication Date: 2014-04-23
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 in organic nonlinear materials and fluorescent probes.

Method used

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  • Top-bottom asymmetrical tert-butyl spirobifluorene compound
  • Top-bottom asymmetrical tert-butyl spirobifluorene compound
  • Top-bottom asymmetrical tert-butyl spirobifluorene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] The preparation of 2,7-di-tert-butyl-2',7'-bis(4-piperidinenaphthalimide)-9,9'-spirobifluorene comprises the following steps:

[0094] (1) Synthesis of 2,7-di-tert-butyl-2',7'-dibromo-9,9'-spirobifluorene

[0095] Refer to the method disclosed in the prior Chinese patent CN 102126963 of the applicant.

[0096] (2) Synthesis of 2,7-di-tert-butyl-2',7'-bis(N-phthalimide)-9,9'-spirobifluorene

[0097]

[0098] Add 2g (3.4mmol) 2,7-di-tert-butyl-2',7'-dibromo-9,9'-spirobifluorene, 2.4g (12.97mmol) phthalimide to the three-necked flask Potassium, 3.2g (16.84mmol) ketone iodide, 30mL DMF, heated to reflux for 12h under the protection of nitrogen. The reaction mixture was cooled to room temperature, a large amount of turbidity appeared after adding concentrated ammonia water, suction filtered, and then extracted with dichloromethane (30mL×2), the solvent was evaporated, and the crude product was separated by column chromatography to obtain 1.342g of a yellow substance wit...

Embodiment 2

[0106] Determination of photoluminescence spectrum of "up-down" asymmetric tert-butylspirobifluorene compound (using 2,7-di-tert-butyl-2', 7'-bis(4-piperidine naphthalimide)- 9,9′-spirobifluorene as an example)

[0107] 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 maximum absorption spectrum of the compound is around 400nm and cuts off at 46nm, which fully meets the 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 500nm, and the maximum emission peak red shifts with the increase of solvent polarity. This shows that the charge in the m...

Embodiment 3

[0109] Thermal analysis of "up-down" asymmetric tert-butyl spirobifluorene compound (using 2,7-di-tert-butyl-2', 7'-bis(4-piperidine naphthalimide)-9, 9′-spirobifluorene as an example)

[0110] The product was thermally analyzed and tested on a Shimadzu DT-40 thermogravimetric analyzer. The operating conditions were: ceramic crucible (without cover), nitrogen atmosphere, air flow rate of 30mL / min, and heating rate of 10.0°C / min. The starting temperature is 25°C and the ending temperature is 800°C. The test results are attached Figure 7 . It can be observed from the figure that when the temperature reaches 385°C, the substance begins to decompose, and when it decomposes 5%, the temperature reaches 448°C. In the DTA curve, there is an obvious exothermic peak. At this time, the peak temperature is 369°C. This peak comes from the crystallization exotherm, and the temperature at this time is the crystallization temperature. After this temperature until 800 ° C, the system has ...

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Abstract

The invention relates to a top-bottom asymmetrical tert-butyl spirobifluorene compound. The compound of the invention has a structural formula as represented by (I), and in the structural formula, R1 can be any one of various electron-withdrawing groups and electron-donating groups, such as a variety of alkyl groups, substituted aryl groups, substituted heterocyclic radicals, substituted alkylene groups, substituted amino groups, chlorine, bromine and iodine, except tert-butyl groups. According to the invention, cheap and easily available 4,4'-di-tert-butyl-biphenyl is used a raw material and reacts with 2,7-biX-fluorenone (wherein X represents substituents) through bromination, X substituents on a fluorene ring are converted into a variety of functional groups, and other steps are also carried out so as to obtain the compound (I). The top-bottom asymmetrical tert-butyl spirobifluorene compound in the invention has the characteristics of low cost, a simple synthesis route, high yield, easiness in industrial production, a special spiro-conjugation effect, good dissolvability, high thermal stability and a wide applicability in the fields of organic light-emitting displays, organic non-linear 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 tert-butyl spirobifluorene compounds 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 the field of optoelectronic materials, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K11/06H01L51/54G02F1/361
Inventor 肖海波殷鸿尧张晓瑛丁磊郭松魁
Owner SHANGHAI NORMAL UNIVERSITY
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