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Efficient synthesis method of novel fluorescent material 1,3-dihydroisobenzofuran compound

A compound and addition technology, applied in the field of spectral properties, can solve problems such as poor atom economy and difficult availability of raw materials

Inactive Publication Date: 2014-11-12
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of these two methods is that the imine needs to be prepared, the raw materials are not easy to obtain, and the required potassium tert-butoxide is equivalent, and the atom economy is not good.

Method used

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  • Efficient synthesis method of novel fluorescent material 1,3-dihydroisobenzofuran compound
  • Efficient synthesis method of novel fluorescent material 1,3-dihydroisobenzofuran compound
  • Efficient synthesis method of novel fluorescent material 1,3-dihydroisobenzofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～20

[0018] Embodiment 1~20 is synthetic embodiment

Embodiment 1

[0020] The preparation of compound shown in formula III a:

[0021]

[0022] Under nitrogen protection, (Z)-1-benzylidene-1,3-dihydroisobenzofuran (62.5mg, 0.3mmol) and 4-dimethylaminobenzaldehyde (67.1mg, 0.45mmol) were dissolved In 1.0mL DMF, potassium tert-butoxide (0.06mmol, 1M in THF) and 18-crown-6 (23.8mg, 0.09mmol) were added under stirring at room temperature, and the reaction mixture was stirred at 110°C for 2 hours and cooled to After room temperature, add saturated ammonium chloride aqueous solution to the mixture to quench the reaction, transfer to a separatory funnel, extract with dichloromethane, combine the extracts, wash with saturated brine, add anhydrous sodium sulfate to dry, filter, spin dry The solvent was separated and purified on a silica gel column to obtain 100.4 mg of a yellow solid (the title compound, compound III a), with a yield of 99%.

[0023] Melting point: 145.6-148.2°C; 1 H NMR (400MHz, CDCl 3 ,25℃)δ7.92(d,J=7.84Hz,2H),7.82(d,J=8.72Hz,...

Embodiment 2

[0025] The preparation of compound shown in formula III b:

[0026]

[0027] According to the method shown in Example 1, only the substrate aromatic aldehyde is changed. The yield of the title compound was 91%.

[0028] Melting point: 195.8-199.2°C; 1 H NMR (400MHz, CDCl 3 ,25℃)δ7.92(d,J=7.44Hz,2H),7.82(d,J=8.72Hz,2H),7.59-7.65(m,2H),7.33-7.46(m,4H),7.21- 7.26(m,1H),6.64(d,J=8.36Hz,2H),6.15(s,1H),6.14(s,1H),3.38(br s,4H),2.04(t,J=6.52Hz, 4H); 13 C NMR (100.6MHz, CDCl 3 ,25℃)δ152.4,148.8,146.8,135.6,134.6,133.2,129.9,129.1,128.6,128.3,128.2,126.1,122.4,119.9,119.3,111.8,100.9,98.3,47.7,25.6, TOHRMS( calcd for C 26 h 24 NO + [M+H] + :366.1852,found:366.1860.

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Abstract

The invention provides a synthesis method for conveniently and rapidly constructing a 1,3-dihydroisobenzofuran fluorescent material. The 1,3-dihydroisobenzofuran compound is large in Stokes shift and adjustable and controllable in fluorescence emission wavelength. The synthesis method comprises one step: carrying out an addition-elimination reaction by taking outer cycloalkene ethers and aromatic aldehydes as raw materials under the catalytic action of potassium tert-butoxide so as to obtain the compound with a structural framework. The 1,3-dihydroisobenzofuran derivatives all have good conjugated structures, so that the compound has strong fluorescence. Especially, the fluorescence property of the compound is more obvious on the basis of the 1,3-dihydroisobenzofuran derivatives containing donor-receptor structures. The maximum emission wavelength of the 1,3-dihydroisobenzofuran derivatives can be adjusted and controlled from 496nm to 597nm by virtue of the introduction of different substituents. Thus, the synthesis method has the characteristics of being high in yield, easily available in raw materials, short in reaction time, simple in aftertreatment and the like. Thus, a foundation for the synthesis of a novel fluorescent compound is provided.

Description

technical field [0001] The invention relates to constructing 1,3-dihydroisobenzofuran fluorescent skeletons with relatively large Stokes shifts, and deeply studies their spectral properties. Background technique [0002] Aromatic rings or aromatic heterocyclic compounds with large conjugated structures usually have strong fluorescence. This kind of fluorescent molecules has attracted the interest and attention of a large number of researchers due to their wide application in biomedicine, dye industry and other fields. Therefore, the synthesis and performance research of aromatic rings or aromatic heterocyclic compounds with large conjugated structures has always been a very important research field in organic chemistry. Starting from simple and easy-to-obtain raw materials, the synthesis of various fluorescent macromolecules with high yield and high selectivity will provide theoretical guidance for the development of organic optoelectronic materials. [0003] Based on the i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/76C09K11/06
CPCC07D311/76C09K11/06C09K2211/1077
Inventor 刘培念商学松李登远
Owner EAST CHINA UNIV OF SCI & TECH
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