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Novel compound, and preparation method and application thereof

A compound and product technology, applied in the field of synthesis of biomedical functional fluorescent molecules, can solve the problems of short emission wavelength, single type, low fluorescence quantum yield, etc.

Active Publication Date: 2020-10-27
XIEHE HOSPITAL ATTACHED TO TONGJI MEDICAL COLLEGE HUAZHONG SCI & TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned compounds have a single type, short emission wavelength, and low fluorescence quantum yield.

Method used

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  • Novel compound, and preparation method and application thereof
  • Novel compound, and preparation method and application thereof
  • Novel compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1 (HBTTPA)

[0059] The 2-(2'-hydroxyphenyl)benzoxazole compound 3-(benzo[d]thiazol-2-yl)-4'-( Bis(4-methoxyphenyl)amino)-[1,1'-biphenyl]-4-alcohol (HBTTPA) (X=S, R in the example 1 = R 2 =H) synthetic, synthetic route is as follows:

[0060]

[0061] Synthesis of compound HBTBr: Weigh 5-bromosalicylaldehyde (301.5 mg, 1.5 mmol) and o-aminothiophenol (187.8 mg, 1.5 mmol) and dissolve them in 5 mL of ethanol solution, add 1 mL of concentrated hydrochloric acid under stirring at room temperature, and then Add 40 μL of 30% hydrogen peroxide solution, and stir the reaction at room temperature for 30 min. After the reaction was completed, it was filtered and recrystallized from ethanol to obtain the compound HBTBr with a yield of 83.7%.

[0062] 1 H NMR (400MHz, CDCl 3 ),δ(ppm):12.55(s,1H),7.99-8.01(d,1H),7.92-7.94(d,1H),7.79-7.80(d,1H),7.51-7.55(m,1H), 7.43-7.47(m,2H); 13 C NMR (100MHz, CDCl 3 ), δ (ppm): 167.77, 157.01, 151.63, 135.31, 132.61, 130.48,...

Embodiment 2

[0065] Example 2 (HBTTPAQ)

[0066] The 2-(2'-hydroxyphenyl)benzoxazole compound 5-(benzo[d]thiazol-2-yl)-4'-( Bis(4-methoxyphenyl)amino)-4-hydroxyl-[1,1'-biphenyl]-3-carbaldehyde (HBTTPAQ) (X=S, R in the example 1 = R 2 =-CHO) The synthetic route is as follows:

[0067]

[0068] Synthesis of compound HBTBr: Weigh 5-bromosalicylaldehyde (301.5 mg, 1.5 mmol) and o-aminothiophenol (187.8 mg, 1.5 mmol) and dissolve them in 5 mL of ethanol solution, add 1 mL of concentrated hydrochloric acid under stirring at room temperature, and then Add 40 μL of 30% hydrogen peroxide solution, and stir the reaction at room temperature for 30 min. After the reaction was completed, it was filtered and recrystallized from ethanol to obtain the compound HBTBr with a yield of 83.7%.

[0069] 1 H NMR (400MHz, CDCl 3 ),δ(ppm):12.55(s,1H),7.99-8.01(d,1H),7.92-7.94(d,1H),7.79-7.80(d,1H),7.51-7.55(m,1H), 7.43-7.47(m,2H); 13 C NMR (100MHz, CDCl 3 ), δ (ppm): 167.77, 157.01, 151.63, 135.31, 1...

Embodiment 3

[0074] Example 3 (HBTTPI)

[0075] The 2-(2'-hydroxyphenyl)benzoxazole compound 3-(benzo[d]thiazol-2-yl)-4'-( 4,5-bis(4-methoxyphenyl)-1-phenyl-1H-imidazol-2-yl)-[1,1'-biphenyl]-4-alcohol (HBTTPI) (X= S, R 1 = R 2 =H) The synthetic route is as follows:

[0076]

[0077] Synthesis of compound HBTBr: Weigh 5-bromosalicylaldehyde (301.5 mg, 1.5 mmol) and o-aminothiophenol (187.8 mg, 1.5 mmol) and dissolve them in 5 mL of ethanol solution, add 1 mL of concentrated hydrochloric acid under stirring at room temperature, and then Add 40 μL of 30% hydrogen peroxide solution, and stir the reaction at room temperature for 30 min. After the reaction was completed, it was filtered and recrystallized from ethanol to obtain the compound HBTBr with a yield of 83.7%.

[0078] 1 H NMR (400MHz, CDCl 3 ),δ(ppm):12.55(s,1H),7.99-8.01(d,1H),7.92-7.94(d,1H),7.79-7.80(d,1H),7.51-7.55(m,1H), 7.43-7.47(m,2H); 13 C NMR (100MHz, CDCl 3 ), δ(ppm): 167.77, 157.01, 151.63, 135.31, 132.61, 130...

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Abstract

The invention discloses a novel compound and a preparation method and application thereof. Specifically, the invention provides a 2-(2 '-hydroxyphenyl) benzoxazole compound which has an excited stateintramolecular proton transfer and aggregation-induced emission characteristic and has a skeleton structure as shown in a general formula I. In the general formula I, R2 is independently selected fromhydrogen, an aldehyde group or an electron-withdrawing unit conjugated with a benzene ring through double bonds; the invention provides a preparation method of a 2-(2 '-hydroxyphenyl) benzoxazole compound. In addition, the invention also provides an application of the 2-(2 '-hydroxyphenyl) benzoxazole compound containing the nitrogen positive ion structure in living cell mitochondrion imaging. The 2-(2 '-hydroxyphenyl) benzoxazole compound with excited state intramolecular proton transfer and aggregation-induced emission effects has a good application prospect in the fields of photoelectricity, sensing, biomedicine and the like.

Description

technical field [0001] The invention belongs to the field of synthesizing functional fluorescent molecules for biomedicine, and specifically relates to a class of 2-(2'-hydroxyphenyl)benzoxazole compounds with excited-state intramolecular proton transfer and aggregation-induced luminescent effects, and the type Compound preparation methods and applications in mitochondria-targeted fluorescence imaging. Background technique [0002] Conventional organic light-emitting materials usually have planar aromatic rings, and generally have high luminous efficiency in dilute solutions, but π-π stacking occurs in concentrated solutions or aggregated states, which increases the loss of non-radiative energy, manifested as a decrease in luminous efficiency Even without emitting light, that is, aggregation-induced luminescent quenching (ACQ), the ACQ effect limits their applications in fields such as organic light-emitting diodes (OLEDs) and biological detection and imaging. In 2001, Acad...

Claims

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Application Information

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IPC IPC(8): C07D277/66C07D417/10C07D417/14C09K11/06G01N21/64
CPCC07D277/66C07D417/10C07D417/14C09K11/06G01N21/6456G01N21/6428G01N21/6402C09K2211/1007C09K2211/1044C09K2211/1029C09K2211/1037C09K2211/1014G01N2021/6439
Inventor 谢明星高瑭吴雅张丽靳巧锋陈逸寒
Owner XIEHE HOSPITAL ATTACHED TO TONGJI MEDICAL COLLEGE HUAZHONG SCI & TECH UNIV
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