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A kind of carbazole-based triphenylamine-oxadiazole fluorescent molecule and its preparation method and application

A carbazolyl triphenylamine and fluorescent molecule technology, applied in the field of fluorescent molecules, can solve problems such as fluorescence quenching, and achieve the effects of high stability, good solubility, and good aggregation-induced luminescence performance

Inactive Publication Date: 2016-08-03
SOUTHEAST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Qian Ying, Luo Manli. Synthesis and efficient three-photonexcited green fluorescence of pyridine-triphenylamine conjugated dyes. Dyes and Pigments, 2014, 101, 240-246 reported that pyridine-triphenylamine-oxadiazole conjugated molecules have strong fluorescence in solution, but their fluorescence is completely quenched in the aggregated state

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  • A kind of carbazole-based triphenylamine-oxadiazole fluorescent molecule and its preparation method and application
  • A kind of carbazole-based triphenylamine-oxadiazole fluorescent molecule and its preparation method and application
  • A kind of carbazole-based triphenylamine-oxadiazole fluorescent molecule and its preparation method and application

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preparation example Construction

[0024] The preparation method of the above-mentioned carbazolyltriphenylamine-oxadiazole fluorescent molecule comprises the following steps: in tetrahydrofuran solution, compound M 1 Under the catalysis of NaH and compound M 2 Carry out Wittig reaction, make compound TM namely described carbazolyltriphenylamine-oxadiazole fluorescent molecule, synthetic route is as follows:

[0025]

Embodiment 1

[0034] Embodiment 1 Preparation of carbazolyl triphenylamine-oxadiazole fluorescent molecule

[0035] 0°C and under nitrogen protection, 1.00g (1.58mmol) of compound M 2 Dissolve in 20mL of tetrahydrofuran (THF) solution, and slowly add 0.06g (2.68mmol) sodium hydride suspension in 5mL THF dropwise. Stir at 0°C for 1 h, slowly dropwise add 1.44 g (1.74 mmol) of compound M 1 20mL THF solution. The temperature was gradually raised to 80°C under stirring, and the reaction was carried out for 2 hours. After the reaction, the reaction solution was cooled to room temperature and poured into water. Solids were precipitated, filtered by suction, dried, purified by column chromatography and recrystallization to obtain TM as a yellow solid with a yield of 50%.

[0036] Analysis of the resulting compound TM:

[0037] 1 HNMR (CDCl 3 ,ppm): δ8.20(s,4H),8.19(d,J=9.43Hz,2H),8.14(d,J=8.37Hz,2H),7.72(d,J=8.25Hz,2H),7.61 -7.58(m,4H),7.58-7.55(m,4H),7.55-7.53(m,4H),7.49-7.44(m,8H),7.36(d,...

Embodiment 2

[0042] Example 2 Aggregation-induced Luminescent Properties of Carbazolyl Triphenylamine-Oxadiazole Fluorescent Molecules

[0043] figure 1 It is the solid-state fluorescence spectrum of the carbazolyltriphenylamine-oxadiazole fluorescent molecule TM. The solid powder of the fluorescent molecule TM in the dark room emits bright green fluorescence under the ultraviolet lamp, and the maximum emission wavelength is 498nm. Carbazolyltriphenylamine-oxadiazole fluorescent molecule TM is insoluble in water, but soluble in organic solvent tetrahydrofuran, and the fluorescence intensity changes with the water content in the water / tetrahydrofuran mixed solution. figure 2 It is the change trend diagram of the fluorescence relative intensity of the carbazolyltriphenylamine-oxadiazole fluorescent molecule TM in the water / tetrahydrofuran mixed solution with different water contents. When the water content increased from 0 to 50%, the fluorescence intensity gradually weakened. When the wa...

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Abstract

The invention discloses a carbazolyl triphenylamine-oxadiazole fluorescent molecule, which is obtained by conjugated connection of 9-carbazolyl triphenylamine and 2,5-diaryl-1,3,4-oxadiazole fluorescent groups through an olefinic bond. The invention further discloses a preparation method of the carbazolyl triphenylamine-oxadiazole fluorescent molecule. The method comprises the following step: carrying out Wittig reaction on a compound M1 and a compound M2 in a tetrahydrofuran solution under catalysis of NaH, so as to prepare the compound MT, namely the carbazolyl triphenylamine-oxadiazole fluorescent molecule. The fluorescent molecule is not reported in the prior art; the aggregation state of the molecule is regulated and controlled by inner rotation limitation of rigid multi-aromatic ring molecules; the fluorescent molecule has good aggregation-induced luminescence property; the high-performance fluorescent nano spheres can be prepared; and the carbazolyl triphenylamine-oxadiazole fluorescent molecule is good in solubleness, high in stability, can be applied to information expression of complicated biological and environmental systems, and has important application value in the fields such as a fluorescence sensor, a biological fluorescent marking and tumor cells imaging.

Description

technical field [0001] The invention relates to the technical field of fluorescent molecules, in particular to a carbazolyl triphenylamine-oxadiazole fluorescent molecule and its preparation method and application. Background technique [0002] Most fluorescent chromophores have good luminescent properties in dilute solutions, but in the aggregated state, due to intermolecular interactions, non-radiative energy conversion or species that are not conducive to fluorescence emission are formed, resulting in weakened fluorescence or even aggregation without luminescence. The phenomenon of fluorescence quenching greatly limits the application of fluorescent molecules. For example, CN101481609A discloses a class of spatially symmetrical multiphoton pump fluorescent materials. The large π conjugated system formed by this material forms a radial multi-dimensional and multi-directional intramolecular charge transfer with the benzene ring as the center, and has a large Strong multiph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14C09K11/06G01N33/52
Inventor 钱鹰曹多军靳永昌
Owner SOUTHEAST UNIV
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