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2, 5-diaryl-1, 3, 4-oxadiazole fluorescent molecule and preparation method thereof

A fluorescent molecule, oxadiazole technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., to achieve the effect of excellent fluorescent emission performance

Inactive Publication Date: 2014-12-10
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Conjugate oxadiazole, triphenylamine and anthracene to form a dendritic high-efficiency fluorescent molecule, which has not been reported in the prior art

Method used

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  • 2, 5-diaryl-1, 3, 4-oxadiazole fluorescent molecule and preparation method thereof
  • 2, 5-diaryl-1, 3, 4-oxadiazole fluorescent molecule and preparation method thereof
  • 2, 5-diaryl-1, 3, 4-oxadiazole fluorescent molecule and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1 prepares compound A

[0015] Dissolve ethyl [1,3,4]-oxadiazole-2,5-dibenzyl phosphate (1.0g, 1.91mmol) in 15mL DMF, under nitrogen protection, slowly add potassium tert-butoxide in ethanol dropwise under full stirring Solution (mass fraction is 30%, 5.65mmol), stirred and reacted for 0.5h. Added 4-[N,N-bis(4-iodophenyl)]benzaldehyde (2.0g, 3.83mmol), heated to 85°C, refluxed 8h. The reaction solution was poured into 50mL of ethanol, a large amount of flocculent precipitates were formed, stood still, and filtered with suction. The obtained solid was washed with hot ethanol several times to obtain 1.5g of yellow-green solid -2,5-bis{4-{4-[ N,N-bis(4-iodophenyl)amino]styrene}phenyl}-[1,3,4]-oxadiazole (A), yield 63%.

[0016] Analysis of the obtained compound A:

[0017] 1 H NMR (300MHz, CDCl 3 )δ:8.16(d,J=8.22Hz,4H),7.68(d,J=J=8.19Hz,4H),7.59(d,J=8.79Hz,8H),7.47(d,J=8.61Hz, 4H),7.24(d,J=18.72Hz,4H),7.08(d,J=8.67Hz,4H),6.89(d,J=8.82,8H)

[0018] The stru...

Embodiment 2

[0021] Embodiment 2 prepares compound B

[0022] Under the protection of anhydrous, oxygen and nitrogen, add 2,5-bis{4-{4-[N,N-bis(4-iodophenyl)amino]styrene}phenyl}- [1,3,4]-Oxadiazole (A) 0.316g (0.25mmol), 9-vinyl anthracene (purchased from Bailingwei Chemical Co., Ltd.) 0.245g (1.20mmol) and palladium acetate (purchased from Bailingwei Chemical Co., Ltd. Co., Ltd.) 0.020g (0.09mmol), tris(o-tolyl)phosphine (purchased from Bailingwei Chemical Co., Ltd.) 0.057g (0.18mmol), potassium phosphate 0.298g (1.40mmol) and 6.00mL of anhydrous DMAc, oil bath Heat to 140°C and reflux for 72 hours. After the reaction, filter to remove impurities, wash with dichloromethane solution, slowly add the solution dropwise to methanol solution, and a yellow solid precipitates. After drying, the product is purified by column chromatography and gradient elution , a light yellow solid was obtained with a yield of 30.8%. m.p.246-247°C.

[0023]

[0024] Analysis of the resulting compound B:

...

Embodiment 3

[0029] The fluorescence detection of embodiment 3 compound B

[0030] Example compound B has excellent fluorescence emission properties, and there is a strong intramolecular charge transfer in the conjugated system, which can be used as a two-photon absorption and fluorescence material. In THF solution, the maximum wavelength of its ultraviolet absorption is 410nm, the maximum wavelength of linear fluorescence is at 519nm, and the fluorescence lifetime is 1.48ns. Excited with 800nm ​​femtosecond laser, the two-photon absorption cross-section is measured as 915GM by two-photon induced fluorescence method, and the two-photon fluorescence wavelength is located at 523nm.

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Abstract

The invention discloses a 2, 5-diaryl-1, 3, 4-oxadiazole type fluorescent compound. The 2, 5-diaryl-1, 3, 4-oxadiazole type fluorescent compound is characterized by taking 2, 5-diaryl-1, 3, 4-oxadiazole as a central core, taking anthracene as a branch-shaped conjugated molecule of an outer-layer group, and combining three fluorescent groups, namely the anthracene, triphenylamine and oxadiazole for preparation, wherein the composition proportion of the fluorescent groups is as follows: anthracene: triphenylamine: oxadiazole=4: 2: 1. The 2, 5-diaryl-1, 3, 4-oxadiazole conjugated molecule disclosed by the invention has very strong intramolecular charge transfer and excellent fluorescence emission performance, and can be used as a two-photon absorption and fluorescent material. The 2, 5-diaryl-1, 3, 4-oxadiazole type fluorescent compound has important application values in the fields of fluorescent probes, chemical sensors, photoelectric switches and high-density optical storage.

Description

technical field [0001] The invention relates to oxadiazole fluorescent molecules, and specifically designs a 2,5-diaryl-1,3,4-oxadiazole fluorescent molecule and a preparation method thereof. Background technique [0002] Intramolecular charge-transfer compounds contain electron donor-acceptor building blocks linked by highly delocalized π-bond conjugation. Intramolecular charge transfer occurs between the electron donor and the electron acceptor under photoexcitation, resulting in a charge transfer excited state. Intramolecular charge transfer compounds can be used as two-photon absorption and fluorescent materials, and have important application prospects in the fields of molecular devices such as fluorescent probes, chemical sensors, and photoelectric switches. Related experimental and theoretical studies have attracted extensive attention. Oxadiazoles have good electron transport properties and chemical stability, while anthracene derivatives have good luminescent prope...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/107C09K11/06
Inventor 钱鹰王彬彬王轶丽管成飞陶在琴
Owner SOUTHEAST UNIV
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