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Isolongifolanone based hexahydroquinazoline-2-amine Schiff base type fluorescent material, and synthetic method and application thereof

A technology of phyllonyl hexahydroquinazoline and amine Schiff base type, which is applied in the field of isolongyl ketone base hexahydroquinazoline-2-amine Schiff base type fluorescent materials and their synthesis, achieving good results Effect of Fluorescence Intensity

Inactive Publication Date: 2017-05-10
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In recent years, there have been some studies on the synthesis and optical properties of organic small molecule fluorescent dyes, such as aza-BODIPY fluorescent dyes, salicylaldehyde azine fluorescent dyes, etc., but no hexahydroquinazolin-2-amine Schiff base has been used for fluorescence reports on dyeing

Method used

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  • Isolongifolanone based hexahydroquinazoline-2-amine Schiff base type fluorescent material, and synthetic method and application thereof
  • Isolongifolanone based hexahydroquinazoline-2-amine Schiff base type fluorescent material, and synthetic method and application thereof
  • Isolongifolanone based hexahydroquinazoline-2-amine Schiff base type fluorescent material, and synthetic method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0032] The synthetic method of isolongylone base hexahydroquinazoline-2-amine Schiff base compound, the synthetic process is:

[0033]

[0034] Specific steps are as follows:

[0035] 1) Preparation of 7-(2'-pyridylmethylene) isolongifanone:

[0036] Add 2.2g of isolongifolanone, 1.07g of pyridine 2-carbaldehyde, 0.51g of sodium ethoxide and 30mL of ethanol into a three-necked flask equipped with a stirrer, a thermometer and a reflux condenser in sequence, and heat to reflux at 80-90°C for React, react for about 4 hours until the conversion rate of isolonganone reaches over 95% (GC tracking detection). The reactant was extracted 3 times with 20 mL of ethyl acetate, the organic phases were combined, and washed several times with saturated brine until neutral; the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to recover the solvent to obtain 7-(2'-pyridine The crude methylene) isolongophallanone crude product is recrystallized with ethano...

Embodiment 2

[0044] A certain amount of 1-(((6,6,10,10-tetramethyl-4-(2′-pyridyl)-5,7,8,9,10,10α-hexahydro-6H-6α, 9-endo-methylenebenzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol is placed on the filter paper, and it is observed that the sample is a light yellow solid as thin as shredded paper, which is To further observe the fluorescence properties of the sample, place it under a 365nm ultraviolet lamp, and find that the sample emits strong yellow-green fluorescence, such as figure 1 Shown, a: the photo of the compound under sunlight; b: the photo of the compound under 365nm ultraviolet lamp; 5,7,8,9,10,10α-hexahydro-6H-6α,9-methanobenzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol solid It has good fluorescent properties and can be used as a fluorescent dye.

Embodiment 3

[0046] A certain amount of 1-(((6,6,10,10-tetramethyl-4-(2′-pyridyl)-5,7,8,9,10,10α-hexahydro-6H-6α, 9-endo-methylenebenzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol is dissolved in a certain volume of ethanol-water solution, and then gauze and filter paper are soaked in it respectively, After fully contacting the moistening foam, dry the filter paper and gauze, and place it under a 365nm ultraviolet lamp, such as figure 2 As shown, a: filter paper after compound impregnation; b: gauze after compound impregnation; c: ethanol-water solution of compound. Good fluorescence intensity, indicating that 1-(((6,6,10,10-tetramethyl-4-(2′-pyridyl)-5,7,8,9,10,10α-hexahydro-6H- 6α,9-Methylenebenzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol can be used as a fluorescent dye with good fluorescence properties.

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Abstract

The invention discloses an isolongifolanone based hexahydroquinazoline-2-amine Schiff base type fluorescent material, and a synthetic method and an application thereof. The synthetic method comprises the following steps: by utilizing a natural and renewable resource, i.e., a longifolene derivative namely isolongifolanone as a raw material, carrying out condensation with 2-pyridinecarbaldehyde so as to obtain 7-(2'-pyridylmethylene)isolongifolanone; subjecting the 7-(2'-pyridylmethylene)isolongifolanone and guanidine hydrochloride to condensation and cyclization so as to obtain 6,6,10,10-tetramethyl-4-(2'-pyridyl)-5,7,8,9,10,10alpha-hexahydro-6H-6alpha,9-methanobenzo[h]quinazoline-2-amine; and carrying out condensation with 2-hydroxyl-1-naphthaldehyde so as to obtain 1-(((6,6,10,10-tetramethyl-4-(2'-pyridyl)-5,7,8,9,10,10alpha-hexahydro-6H-6alpha,9-methanobenzo[h]-2-quinolyl)imido)methyl)naphthalene-2-phenol. The compound is luminous yellow in sunlight and can emit luminous yellow green fluorescence under irradiation of ultraviolet light with a wave length of 365 nm.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to an isolongifanonyl hexahydroquinazoline-2-amine Schiff base type fluorescent material and its synthesis method and application. Background technique [0002] Among the light-emitting materials, the research on organic small molecule light-emitting materials has attracted more and more people's attention. There are many types and rich colors, and because of its simple structure and easy adjustment, the research is becoming more and more extensive. Compared with inorganic light-emitting materials, organic small molecule materials With higher luminous efficiency and wider luminous color range, it is often used in optical electronic devices, photochemical sensors, DNA staining, cell staining, dyes, etc. However, most of the currently known organic small molecule light-emitting materials are prone to fluorescence quenching under solid-state conditions, so this makes small...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C09K11/06C09B57/00
CPCC07D401/04C09B57/00C09K11/06
Inventor 王石发王忠龙徐徐谷文杨益琴匡洪波杨丽娟姜倩王芸芸刘艳芳张燕
Owner NANJING FORESTRY UNIV
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