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Thiazole compound with strong two-photon effect and synthesis method thereof

A two-photon and compound technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., to achieve long fluorescence lifetime, novel structure, and good solubility

Inactive Publication Date: 2013-04-24
ANHUI UNIVERSITY
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Problems solved by technology

[0003] Although the two-photon phenomenon was experimentally confirmed in the 1960s, there were few reports on the practical application of the two-photon effect before the 1980s

Method used

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  • Thiazole compound with strong two-photon effect and synthesis method thereof
  • Thiazole compound with strong two-photon effect and synthesis method thereof
  • Thiazole compound with strong two-photon effect and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0032] 1. Preparation of Intermediate M:

[0033] Add 25.00g (0.2mol) of p-fluorobenzaldehyde, 51.20g (0.7mol) of diethylamine, 250mL of dimethyl sulfoxide and 41.50g of anhydrous potassium carbonate in a 500mL round bottom flask, add 0.50mL of Aliquat336, stir and reflux for 72h , cooled to room temperature, poured into ice water and stirred, a large amount of light yellow precipitate appeared, put it in the refrigerator at -15-10°C for 30 minutes and then more precipitate appeared, and the light yellow crystal was obtained by suction filtration. Separation by silica gel column chromatography, petroleum ether: ethyl acetate = 10:1, and vacuum drying to obtain 32.92 g of intermediate M with a yield of 93%.

[0034] 1 H NMR (CDCl 3 ,400MHz):δ=1.20(t,6H,J=7.11Hz),3.42(q,2H,J=7.02Hz),6.68(d,2H,J=8.84Hz),7.70(d,2H,J= 8.79Hz), 9.69(s, 1Hc).

[0035] 2. Preparation of the target product:

[0036] Weigh 2.00g (11.3mmol) N, N-diethylbenzaldehyde in a 100mL round-bottomed flask, t...

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Abstract

The invention discloses a thiazole compound with a strong two-photon effect and a synthesis method thereof. The structural formula of the thiazole compound with strong two-photon effect is as follows: the thiazole compound is small organic molecule two-photon fluorescence material with strong two-photon effect and has strong single photon fluorescence and two-photon fluorescence, a short wave of 690nm and a long wave of 790nm have larger two-photon absorption cross sections which respectively reach 1282GM and 763GM. The thiazole compound has the characteristics of low excitation energy and good solubleness and the like, has longer fluorescent lifetime in different solvent, and has an obvious application value, wherein the fluorescent lifetime in ethanol is the longest (1.73ns).

Description

1. Technical field [0001] The invention relates to a two-photon fluorescent material and a preparation method thereof, in particular to a thiazole compound with strong two-photon effect and a synthesis method thereof. 2. Background technology [0002] With the development of modern science and technology, photoelectric functional materials based on photons (electrons) have been developed rapidly. Among them, nonlinear optical materials characterized by two-photon absorption have attracted widespread attention. The development of high-tech plays a very important role and influence. Since the end of the last century, there have been more and more reports on strong two-photon materials, and the research objects have also been greatly expanded, from inorganic materials and organic materials to organic / inorganic hybrid materials, nanomaterials, etc., and have Major breakthroughs, research results published in internationally renowned journals such as Nature, Science, and JACS. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C09K11/06
Inventor 吴杰颖聂翠云陈彦昕孙璐周家正李胜利周虹屏孔林田玉鹏
Owner ANHUI UNIVERSITY
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