CN107118214A - The synthetic method of Yi Zhong perylene compounds - Google Patents
The synthetic method of Yi Zhong perylene compounds Download PDFInfo
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- CN107118214A CN107118214A CN201710331664.XA CN201710331664A CN107118214A CN 107118214 A CN107118214 A CN 107118214A CN 201710331664 A CN201710331664 A CN 201710331664A CN 107118214 A CN107118214 A CN 107118214A
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- perylene
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- tetracarboxylic acid
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- acid diimides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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Abstract
The synthetic method of a perylene compound, the invention discloses a kind of 1 rosickyite alcohol radical 3,4:The synthetic method of 9,10 perylene tetracarboxylic acid diimides, step is as follows：By 1 nitro 3,4;9,10 perylene tetracarboxylic acid diimides are mixed with potassium carbonate to be dissolved in polar organic solvent, agitation and dropping propanethiol, react at room temperature 0.5 1.0 hours, reacted solution is added dropwise in the hydrochloric acid solution that concentration is 2moL/L, separates out precipitation, filtering, distillation water washing, dry, purify to obtain product.The synthesising method reacting condition of the present invention is gentle, and reactions steps are simple, easily-controllable, and obtained products collection efficiency is higher.
Description
Technical field
The present invention relates to the synthetic method of Yi Zhong perylene compounds, belong to technical field of organic synthesis.
Background technology
Perylene diimide derivative has good photo and thermal stability, high fluorescence quantum yield, unique redox
Performance and photoelectric property, so as to be widely used in liquid crystal material, photoelectric material, organic solar batteries, organic effect crystal
The field such as pipe and light emitting diode, is the generally acknowledged organic dyestuff with high value of a class.Dui perylene diimide class chemical combination
Thing is performed the derivatization, the compound that mainly to realize synthesis by modifying its acid amides position and gulf two methods different.Both
The influence of position Dui Yu perylene diimides derivatives has very big difference.The dissolving of the main Ying Xiang perylene diimides derivatives in acid amides position
Degree, gulf position carries out rosickyite alcoholization and can directly connect shadow ringing the arrangement of perylene nuclear electron, thus shadow ring perylene diimides derivative absorption and
Fluorescence property, is a kind of important derivatization method.
At present, carrying out rosickyite alcoholization to perylene diimide gulf position can be by by 1- nitro -3,4;The acyl of 9,10- perylene tetracarboxylic acids two
Imines is mixed with potassium carbonate to be dissolved in chloroform solvent, agitation and dropping propanethiol, and the lower heating response of argon gas protection is obtained for 10 hours, is produced
Rate is 35%（X. Kong et al. Dyes and Pigments 95 (2012) 450-454）.Reaction time is long, yield compared with
It is low.Therefore, other convenience and high-efficiencies, gentle controllable derivatization method are sought and synthesize chemical particularly significant to Feng Fu perylene diimides.
The content of the invention
For above-mentioned prior art, it is an object of the invention to provide the synthetic method of Yi Zhong perylene compounds.
To achieve the above object, the present invention is adopted the following technical scheme that：
A perylene compound 1- rosickyite alcohol radical -3,4:9,10- perylene tetracarboxylic acid diimides, its structural formula is as follows：
The synthetic method of described Yi Zhong perylene compounds, it is characterised in that step is as follows：
By 1- nitros -3,4;9,10- perylene tetracarboxylic acid diimides are mixed with potassium carbonate to be dissolved in polar organic solvent, agitation and dropping
Propanethiol, is reacted at room temperature 0.5-1.0 hours, reacted solution is added dropwise in the hydrochloric acid solution that concentration is 2moL/L, separated out
Water washing is distilled in precipitation, filtering, is dried, is purified to obtain 1- rosickyite alcohol radicals -3,4:9,10- perylene tetracarboxylic acid diimides.
The synthetic method of described Yi Zhong perylene compounds, it is characterized in that, the consumption of the potassium carbonate is every gram of 1- nitro -3,
4;9,10- perylene tetracarboxylic acid diimides are with 0.5-2 grams.
The synthetic method of described Yi Zhong perylene compounds, it is characterized in that, the consumption of the propanethiol is every gram of 1- nitro -3,
4;9,10- perylene tetracarboxylic acid diimides are with 20-60 milliliters.
The synthetic method of described Yi Zhong perylene compounds, it is characterized in that, the consumption of the polar organic solvent is every gram of 1-
Nitro -3,4;9,10- perylene tetracarboxylic acid diimides are with 40-200 milliliters.
The synthetic method of described Yi Zhong perylene compounds, it is characterized in that, described polar organic solvent is N- methylpyrroles
Alkanone.
The synthetic method of described Yi Zhong perylene compounds, it is characterized in that, purifying is used with dichloromethane and petroleum ether
Mixed solvent is mobile phase, silica gel column chromatography purifying.
The perylene compound 1- rosickyite alcohol radical -3,4 of this invention:9,10- perylene tetracarboxylic acid diimides synthetic routes are as follows：
1- rosickyite alcohol radical -3,4 synthesized by the inventive method:1 introducing of 9,10- perylene tetracarboxylic acid diimides , perylenes gulfs position
Rosickyite alcohol radical auxochrome, effectively changes 3,4:The electronic structure of 9,10- perylene tetracarboxylic acid diimides, have adjusted its light thing
Rationality matter, enhances solubility in organic solvent, has in terms of organic solar batteries, photoelectric material and potentially should
With value
The beneficial effects of the invention are as follows：The synthesising method reacting condition of the compound is gentle, and reactions steps are simple, easily-controllable, obtain
Products collection efficiency it is higher, yield is up to more than 60%.
Brief description of the drawings
Fig. 1 is compound 1- rosickyite alcohol radical -3,4 prepared by embodiment 1:The mass spectrum of 9,10- perylene tetracarboxylic acid diimides；
Fig. 2 is compound 1- rosickyite alcohol radical -3,4 prepared by embodiment 1:The nucleus magnetic hydrogen spectrum of 9,10- perylene tetracarboxylic acid diimides.
Embodiment
The present invention is further illustrated by the following examples.
Embodiment 1
In 50 mL flasks, 1- nitros -3,4 are added;9,10- perylene tetracarboxylic acid diimides（0.2 g, 0.34 mmol）, carbonic acid
Potassium（0.2 g）With 20 mL 1-METHYLPYRROLIDONEs, sonic oscillation dissolves it, is stirred at room temperature down, and 8.0 mL propanethiols are added dropwise,
TLC tracking reactions, react at room temperature 0.5 hour, stop reaction, and it is 2moL/L's that reacted solution is added dropwise into 100 ml concentration
In hydrochloric acid solution, precipitation is separated out, vacuum filtration distills water washing（50 ml×3）, 70 DEG C are dried in vacuo 5 hours.Crude product leads to
Cross silica gel column chromatography（Dichloromethane：Petroleum ether=4:1）Isolate and purify, obtain 1- rosickyite alcohol radicals -3,4:The acyl of 9,10- perylene tetracarboxylic acids two
Imines 130mg, yield is 61%.Fig. 1 is the mass spectrogram of compound manufactured in the present embodiment, and Fig. 2 is prepared by the embodiment of the present invention
The hydrogen nuclear magnetic resonance spectrogram of compound.
Embodiment 2
In 50 mL flasks, 1- nitros -3,4 are added;9,10- perylene tetracarboxylic acid diimides（0.2 g, 0.34 mmol）, carbonic acid
Potassium（120 mg）With 20mL 1-METHYLPYRROLIDONEs, sonic oscillation dissolves it, is stirred at room temperature down, and 8.0 mL propanethiols are added dropwise,
TLC tracking reactions, are reacted at room temperature 1 hour, stop reaction, and reacted solution is added dropwise into the salt that 100 ml concentration are 2moL/L
In acid solution, precipitation is separated out, vacuum filtration distills water washing（50 ml×3）, 70 DEG C are dried in vacuo 5 hours.Crude product passes through
Silica gel column chromatography（Dichloromethane：Petroleum ether=4:1）Isolate and purify, obtain 1- rosickyite alcohol radicals -3,4:The acyl of 9,10- perylene tetracarboxylic acids two is sub-
Amine 132mg, yield is 62%.
Embodiment 3
In 50 mL flasks, 1- nitros -3,4 are added;9,10- perylene tetracarboxylic acid diimides（0.1 g, 0.34 mmol）, carbonic acid
Potassium（0.1g）With 15mL 1-METHYLPYRROLIDONEs, sonic oscillation dissolves it, is stirred at room temperature down, and 5.0 mL propanethiols are added dropwise,
TLC tracking reactions, react at room temperature 0.5 hour, stop reaction, and it is 2moL/L's that reacted solution is added dropwise into 100 ml concentration
In hydrochloric acid solution, precipitation is separated out, vacuum filtration distills water washing（50 ml×3）, 70 DEG C are dried in vacuo 5 hours.Crude product leads to
Cross silica gel column chromatography（Dichloromethane：Petroleum ether=4:1）Isolate and purify, obtain 1- rosickyite alcohol radicals -3,4:The acyl of 9,10- perylene tetracarboxylic acids two
Imines 66mg, yield is 62%.
Claims (7)
1. a perylene compound 1- rosickyite alcohol radical -3,4:9,10- perylene tetracarboxylic acid diimides, it is characterised in that the compound
Structural formula is as follows：
。
2. the synthetic method of the Yi Zhong perylene compounds described in claim 1, it is characterised in that step is as follows：
By 1- nitros -3,4;9,10- perylene tetracarboxylic acid diimides are mixed with potassium carbonate to be dissolved in polar organic solvent, agitation and dropping
Propanethiol, is reacted at room temperature 0.5-1.0 hours, reacted solution is added dropwise in the hydrochloric acid solution that concentration is 2moL/L, separated out
Precipitation, filtering, distillation water washing, dries, purifies to obtain 1- rosickyite alcohol radicals -3,4:9,10- perylene tetracarboxylic acid diimides.
3. the synthetic method of Yi Zhong perylene compounds according to claim 2, it is characterized in that, the consumption of the potassium carbonate is every
Gram 1- nitros -3,4;9,10- perylene tetracarboxylic acid diimides are with 0.5-2 grams.
4. the synthetic method of Yi Zhong perylene compounds according to claim 2, it is characterized in that, the consumption of the propanethiol is every
Gram 1- nitros -3,4;9,10- perylene tetracarboxylic acid diimides are with 20-60 milliliters.
5. the synthetic method of Yi Zhong perylene compounds according to claim 2, it is characterized in that, the use of the polar organic solvent
Measure as every gram of 1- nitro -3,4;9,10- perylene tetracarboxylic acid diimides are with 40-200 milliliters.
6. the synthetic method of Yi Zhong perylene compounds according to claim 2, it is characterized in that, described polar organic solvent is
1-METHYLPYRROLIDONE.
7. the synthetic method of Yi Zhong perylene compounds according to claim 2, it is characterized in that, purifying is used with dichloromethane
Alkane and petroleum ether mixed solvent are mobile phase, silica gel column chromatography purifying.
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Granted publication date: 20190503 Termination date: 20200512 |