CN104262396A - Bay-position gold-substituted perylene diimide derivative - Google Patents

Bay-position gold-substituted perylene diimide derivative Download PDF

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CN104262396A
CN104262396A CN201410456992.9A CN201410456992A CN104262396A CN 104262396 A CN104262396 A CN 104262396A CN 201410456992 A CN201410456992 A CN 201410456992A CN 104262396 A CN104262396 A CN 104262396A
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derivative
perylene diimides
gulf
pdi
perylene
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CN104262396B (en
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刘秀杰
张琪
孟祥太
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Tianjin University of Technology
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Abstract

The invention discloses a bay-position gold-substituted perylene diimide derivative with a chemical formula of R2-PDI-R1 and a structural formula described in the specification, wherein in a derivative PDI-a, R1 is PPh3 and R2 is H; in a derivative compound PDI-b, R1 is PPh3 and R2 is Au-PPh3; or in the derivative compound PDI-b, R1 is that C is equivalent to N-Ph, and R2 is H. A preparation method of the bay-position gold-substituted perylene diimide derivative comprises the following steps: (1) synthesizing a perylene diimide derivative; and (2) synthesizing a gold-containing derivative. The bay-position gold-substituted perylene diimide derivative prepared by the method is obviously enhanced in fluorescence, stable in property and good in thermal conductivity, and has a wide application prospect in aerospace, photoelectricity, machinery and the like.

Description

Position, a kind of gulf gold replaces perylene diimides derivative
Technical field
She of the present invention is Ji perylene diimides derivative, and position, a kind of gulf gold replaces perylene diimides derivative specifically.
Background technology
Perylene diimides (perylene diimide, PDI) was proposed by Friedlander first in 1913, caused the whole world to pay close attention to widely immediately.Just start, due to the poor cause of its solvability, to be only used to dyestuff and coatings industry.Afterwards by the different sites of Xiu Shi perylene diimides, get to great Liang perylene diimides derivative, be widely used in various field, comprise aerospace, electronics and microelectronics, unicircuit, semi-conductor etc., be employed again recent years and fluorescent probe, medicine, inseparable with the development of the mankind.Perylene diimides derivative is Chenged in people's research with He, mainly realize the different compound of synthesis by modifying its acid amides position and position, gulf.Mainly in atom N, different functional groups is introduced, as alkyl and halogen in acid amides position; Can introduce much different groups in position, gulf, this is also the problem that research is more popular at present.This two kinds of positions impact on Yu perylene diimides derivative has very large difference.The solubleness of acid amides position main Ying Xiang perylene diimides derivative, the position of position, the gulf then fluorescent characteristic of Ying Xiang perylene diimides derivative, absorption peak and emission peak.
Perylene diimides derivative is a large pi-conjugated structure of rigid plane and n-type semiconductor structure.Perylene diimides derivative itself is an electron deficiency system and can regards one as and closed close color base group, if by some electron-withdrawing groups as halogen, nitro replace, its absorption peak and emission peak and fluorescent effect all can reduce, introduce some alkoxyl groups and then can make absorption peak red shift, fluorescence intensity strengthens.
It is a lot of that the supramolecular aggregation that Yi perylene diimides derivative is formed for parent is studied.This aggregate can be formed in several ways, as formed aggregate by coordinate bond; Form aggregate with Zn atom, ferrocene, pyridine derivate, generate various structures, have rectangle, square, trilateral etc., and then show different nature and characteristics; Secondly piled up by pi-pi bond and formed, in different solvents, its aggregation extent is different, studies its chemical property, obtains different gathering constant, Gibbs energy and photovoltaic effect, be widely used in field of nanometer technology; Also by hydrogen bond induced synthesis aggregate, be combined with OPV by hydrogen bond, combine with pi-pi bond and study its photoelectric property, photophysical property, be widely used in a lot.
The self-assembly of perylene diimides derivative comprises several method: 1) based on the self-assembly of solution, the performance of this process is a thermodynamic process, pi-pi accumulation is in occupation of predominant intermolecular forces, this power is greater than hydrophobic forces, result is pi-pi accumulation direction along the longitudinal, thus form a series of different solid, this wherein shows different forms in different solvents, by some physical methods as X diffraction obtains different arrangement modes, this research is applied in the report of nanometer soft material at present, achieves effective control of molecular switch; 2) based on the molecular self-assembling that surface is supported, solvent generally evaporates by this process, this is the mode based on a pile nanostructure in fact, the difference assembling form of solvent is also different, and general some mixed solvents of selection, make it produce some stacked form by the mode of some physics or chemistry, its result is being measured by physical side metering method, as obtained a pile nanostructure by evaporating solvent, layer overlay film bottom it, in gas sensor, application is very wide.
Perylene diimides derivative is studied extensively in liquid crystal material.The liquid crystal shape that the column that perylene diimides derivative is formed is piled up, character is different from its substituting group a great difference, absorption peak and emission peak red shift in Dui Yu perylene diimides derivative sole body, there is not fluorescence quenching in accumulation process, this shape makes it be applied in polaroid and other electricity luminous element processed, the different alkoxyl group of the synthesis such as Thelakkat replaces and triethylene Glycol replaces perylene diimides derivative, its character is studied based on these two kinds of systems of compounds, find that effect is very desirable, as the discotic liquid-crystalline molecules that Yi perylene diimides derivative is skeleton, temperature can arrive 300 degree, mobility significantly promotes, be widely used in solar cell, make use of sun power greatly, can alleviating energy crisis to a certain extent, current related products puts goods on the market, reaction very well.
The applied research of perylene diimides derivative in light, comprises light stream and amplifies, as Photoreceptors and as photoswitch.Utilize light stream to amplify and be mainly used in electroplating industry, the product property of formation is stable, output is large, side effect is little; As Photoreceptors, generate agent mainly as electric charge, and then amplify its photoconductive effect, the color of product also can alter a great deal, and its photoelectric sensitivity is strengthened, is mainly used in xerographic printer; As photoswitch, Wasielewski has synthesized D-A-D molecular switch model, and this breaker in middle is changed stable, rapid and cheap under light action, is easy to implement.
Perylene diimides derivative is in the application of biological field, and general action, in the medicine of DNA, mainly contains two kinds: 1) act in DNA double spirane structure; 2) act in base pair.Perylene diimides derivative has the large pi-conjugated structure of rigid plane, and its reduzate acts in base pair, can make DNA cleavage, reaches the effect for the treatment of.Act predominantly on A-T base pair, bonding force is very high, and effect is fine, and this technology is mainly used in the research of cancer therapy drug, and substituting group is different, the characteristic noticeable change of product, and the character of some compounds can occur on the contrary, to cause great interest.Perylene diimides derivative is also applied in other a lot of aspects, as fluorescent probe, plasma technology, clone technology, cell engineering, dye techniques etc.
Summary of the invention
The object of the invention is for above-mentioned technical Analysis, thering is provided position, a kind of gulf gold to replace perylene diimides derivative and preparation method thereof Tong Guo perylene glycosides and contain golden compound is that parent finally synthesizes required target compound through series reaction, and then studies its character.
Technical scheme of the present invention:
Position, gulf gold replaces a perylene diimides derivative, and its chemical general formula is R 2-PDI-R 1, structural formula is
，
In formula: R in derivative PDI-a 1for PPh 3, R 2for H;
R in derivative compound PDI-b 1for PPh 3, R 2for Au-PPh 3;
r in derivative compound PDI-b 1for C ≡ N-Ph, R 2for H.
Position, described gulf gold replaces a preparation method for perylene diimides derivative, and step is as follows:
(the synthesis of 1) perylene diamide derivatives
1), Jiang the 1:3:3 mixing in molar ratio of perylene glycosides, 2-aminopentane and imidazoles, is heated to 160 DEG C under nitrogen protection, reaction 3-4 hour, and then through extraction, filtration, column chromatography, get is Dao perylene diimides;
2) using chloroform as solvent, Shang Shu perylene diimides is mixed with salt of wormwood, bromine water, heated and stirred refluxes 4 hours, then add S-WAT to remove unnecessary bromine perylene diimides, bromine water, salt of wormwood, the mol ratio of S-WAT is 1:3:4: 6, through extraction, filtration, column chromatography, obtain bromo perylene diimides product;
3) using Diisopropylamine as solvent, by above-mentioned bromo perylene diimides and four triphenyl phosphorus palladiums, three ethynyl silane and cuprous iodide in molar ratio 1:0.1:1:0.05 mix, 40 DEG C are stirred 24 hours under nitrogen protection, through column chromatography, obtain position, gulf ethynyl silane substituted perylene diimides compound;
4) using methylene dichloride and methyl alcohol as solvent, by position, above-mentioned gulf ethynyl silane substituted perylene diimides and salt of wormwood in molar ratio 1:1.5 mix, react under nitrogen protection after 0.5 hour and be spin-dried for, after column chromatography, obtain position, gulf ethynyl and replace perylene diimides;
(2) containing the synthesis of golden derivative
1) using distilled water and ethanol as solvent, by hydrochloro-auric acid and tetramethylene sulfide in molar ratio 1:1 mix, stirred at ambient temperature 15 minutes, will obtain white sediment and scrape and drain;
2) using methylene dichloride as solvent, rear white sediment and different R is drained by above-mentioned 1the raw material replaced is by mixing mol ratio 1:1 mixing, and stirred at ambient temperature 20 minutes, is spin-dried for, adds ethyl alcohol recrystallization, obtain white solid after draining;
3) using methylene dichloride and methyl alcohol as solvent, position, gulf ethynyl is replaced perylene diimides and above-mentioned white solid and sodium hydroxide in molar ratio 1:1:1 mix, stir 15 hours under normal temperature, after column chromatography, obtain position, gulf gold and replace perylene diimides derivative.
Concrete synthetic route is as follows;
，
PDI-Br
，
，
In formula: R in derivative PDI-a 1for PPh 3, R 2for H;
R in derivative PDI-b 1for PPh 3, R 2for Au-PPh 3;
r in derivative PDI-b 1for C ≡ N-Ph, R 2for H.
Advantage of the present invention is: the perylene diimides derivative that position, gulf gold prepared by the method replaces, and fluorescence obviously strengthens and stable in properties, and thermal conductance is well-behaved, at aerospace, photoelectricity.Many aspects such as machinery have a wide range of applications.
[ accompanying drawing explanation]
Fig. 1 is the fluorescence intensity of derivative PDI-a.
Fig. 2 is the fluorescence intensity of derivative PDI-b.
Fig. 3 is the fluorescence intensity of derivative PDI-c.
[ embodiment]
Position, a kind of novel gulf of the present invention gold is below provided to replace the embodiment of the synthesis of perylene diimides derivative.
Embodiment 1;
Position, gulf gold replaces a perylene diimides derivative PDI-a, and its chemical general formula is R 2-PDI-R 1, structural formula is
，
In formula: R in derivative PDI-a 1for PPh 3, R 2for H.
Position, described gulf gold replaces the preparation method of perylene diimides derivative, and step is as follows:
(the synthesis of 1) perylene diamide derivatives
1) in the test tube of band arm, ， is Jiang the 1:3:3 mixing in molar ratio of perylene glycosides, 2-aminopentane and imidazoles, and be heated to 160 DEG C under nitrogen protection, react 3 hours, then through dichloromethane extraction, filtration, column chromatography, the developping agent of column chromatography is CH 2cl 2(the column chromatography operation related in following steps is all like this), get is Dao perylene diimides;
2) in 100 milliliters of single port bottles, using chloroform as solvent, Shang Shu perylene diimides is mixed with salt of wormwood, chloroform, bromine water, heated and stirred refluxes 4 hours, then adds S-WAT to remove unnecessary Xiu ， perylene diimides, bromine water, salt of wormwood, the mol ratio of S-WAT is 1:3:4: 6, through extraction, filtration, column chromatography, obtains bromo perylene diimides product;
3) in the test tube of band arm, using Diisopropylamine as solvent, 1mmol bromo perylene diimides is added successively, the four triphenyl phosphorus palladiums of 0.1mmol ,the three ethynyl silane of 1mmol, the cuprous iodide of 0.05mmol and the Diisopropylamine of 2ml also mix, and 40 DEG C are stirred 24 hours under nitrogen protection, through column chromatography, obtain position, gulf ethynyl silane substituted perylene diimides compound;
4) in 100 milliliters of single port bottles, with methylene dichloride, methyl alcohol is as solvent, add 1mmol ethynyl silane substituted perylene diimides successively, 1.5mmol salt of wormwood, react under nitrogen protection after 0.5 hour and be spin-dried for, after column chromatography, obtain position, gulf ethynyl and replace perylene diimides;
(2) containing the synthesis of golden derivative
1) in 100 milliliters of single port bottles, using distilled water and ethanol as mixed solvent, 1mmol hydrochloro-auric acid is added successively, 18 ml distilled waters, 45 milliliters of ethanol, mix rear slow dropping 1mmol tetramethylene sulfide,, stirred at ambient temperature 15 minutes, will obtain white sediment and scrape and drain;
2) in 100 milliliters of single port bottles, using methylene dichloride as solvent, add that 1mmol is above-mentioned drains rear white sediment, 1mmol R successively 1the raw material triphenyl phosphorus replaced and 20 milliliters of CH 2cl 2, stirred at ambient temperature 20 minutes, is spin-dried for, adds ethyl alcohol recrystallization, obtain white solid after draining;
3) in the test tube of band arm, using methyl alcohol and methylene dichloride as solvent, add position, 1mmol gulf ethynyl successively and replace perylene diimides, the above-mentioned white solid of 1mmol, 10 ml methanol, 10 milliliters of CH 2cl 2, 1mmol sodium hydroxide, stirs 15 hours under normal temperature, after column chromatography, obtains position, gulf gold and replaces perylene diimides derivative.
The master data of compound PDI-a:
1H?NMR?(400?MHz，?Chloroform- d)?δ?11.09?(d，? J?=?8.2?Hz，?1H)，?8.95?(s，?1H)，?8.66?(m，? J?=?8.0?Hz，?5H)，?7.70?–?7.50?(m，?15H)，?5.08?(m，? J?=?15.6Hz，?2H)，?2.38?–?2.20?(m，?4H)，?1.95?(m，? J?=?13.6Hz，?4H)，?0.94?(m，? J?=?7.4Hz，?12H).
Fig. 1 is the fluorescence intensity of derivative PDI-a, shows in figure: fluorescence obviously strengthens and stable in properties.
Embodiment 2:
Position, gulf gold replaces a perylene diimides derivative PDI-b, and its chemical general formula is R 2-PDI-R 1, structural formula is
，
In formula: R in derivative PDI-b 1for PPh 3, R 2for Au-PPh 3.
Position, described gulf gold replaces the preparation method of perylene diimides derivative, and step is substantially the same manner as Example 1, and difference is that the molar weight of step 3) white solid in the synthesis containing golden derivative is 2, is 2 times in embodiment 1.
The master data of compound PDI-b:
1H?NMR?(400?MHz，?Chloroform- d)?δ?10.79?(d，? J?=?8.3?Hz，?2H)，?8.90?(d，? J?=?16.0Hz，2Hz)，8.67(d，? J?=?8.3?Hz，?2H)，?7.66?–?7.44?(m，?30H)，?5.05?(m，? J?=?9.8Hz，?2H)，?2.35?–?2.16?(m，?4H)，?1.91?(m，? J?=?14.0?Hz，?4H)，?0.96?–?0.79?(m，?12H).
Fig. 2 is the fluorescence intensity of derivative PDI-b, shows in figure: fluorescence obviously strengthens and stable in properties.
Embodiment 3:
Position, gulf gold replaces a perylene diimides derivative PDI-c, and its chemical general formula is R 2-PDI-R 1, structural formula is
，
In formula: R in derivative PDI-c 1for C ≡ N-Ph, R 2for H.
Position, described gulf gold replaces the preparation method of perylene diimides derivative, and step is substantially the same manner as Example 1, and difference is: (2) are containing the step 2 of the synthesis of golden derivative) in the raw material R that adds 1for C ≡ N-Ph.
The master data of compound PDI-c
1H?NMR?(400?MHz，?Chloroform- d)?δ?10.90?(s，?1H)，?8.83?(s，?1H)，?8.63?(d，? J?=?19.3?Hz，?5H)，?7.64?–?7.51?(m，?5H)，?5.07?(m，? J?=?11.1Hz，?2H)，?2.27?(m，? J?=?13.8Hz，?4H)，?2.03?–?1.87?(m，?4H)，?0.96?–?0.82?(m，?12H).
Fig. 3 is the fluorescence intensity of derivative PDI-c, shows in figure: fluorescence obviously strengthens and stable in properties.

Claims (2)

1. a perylene diimides derivative for position, gulf gold replacement, is characterized in that chemical general formula is R 2-PDI-R 1, structural formula is
，
In formula: R in derivative PDI-a 1for PPh 3, R 2for H;
R in derivative compound PDI-b 1for PPh 3, R 2for Au-PPh 3;
r in derivative compound PDI-b 1for C ≡ N-Ph, R 2for H.
2. a preparation method for the perylene diimides derivative of position, gulf gold replacement as claimed in claim 1, is characterized in that step is as follows:
(the synthesis of 1) perylene diamide derivatives
1), Jiang the 1:3:3 mixing in molar ratio of perylene glycosides, 2-aminopentane and imidazoles, is heated to 160 DEG C under nitrogen protection, reaction 3-4 hour, and then through extraction, filtration, column chromatography, get is Dao perylene diimides;
2) using chloroform as solvent, Shang Shu perylene diimides is mixed with salt of wormwood, bromine water, heated and stirred refluxes 4 hours, then add S-WAT to remove unnecessary bromine perylene diimides, bromine water, salt of wormwood, the mol ratio of S-WAT is 1:3:4: 6, through extraction, filtration, column chromatography, obtain bromo perylene diimides product;
3) using Diisopropylamine as solvent, by above-mentioned bromo perylene diimides and four triphenyl phosphorus palladiums, three ethynyl silane and cuprous iodide in molar ratio 1:0.1:1:0.05 mix, 40 DEG C are stirred 24 hours under nitrogen protection, through column chromatography, obtain position, gulf ethynyl silane substituted perylene diimides compound;
4) using methylene dichloride and methyl alcohol as solvent, by position, above-mentioned gulf ethynyl silane substituted perylene diimides and salt of wormwood in molar ratio 1:1.5 mix, react under nitrogen protection after 0.5 hour and be spin-dried for, after column chromatography, obtain position, gulf ethynyl and replace perylene diimides;
(2) containing the synthesis of golden derivative
1) using distilled water and ethanol as solvent, by hydrochloro-auric acid and tetramethylene sulfide in molar ratio 1:1 mix, stirred at ambient temperature 15 minutes, will obtain white sediment and scrape and drain;
2) using methylene dichloride as solvent, rear white sediment and different R is drained by above-mentioned 1the raw material replaced is by mixing mol ratio 1:1 mixing, and stirred at ambient temperature 20 minutes, is spin-dried for, adds ethyl alcohol recrystallization, obtain white solid after draining;
3) using methylene dichloride and methyl alcohol as solvent, position, gulf ethynyl is replaced perylene diimides and above-mentioned white solid and sodium hydroxide in molar ratio 1:1:1 mix, stir 15 hours under normal temperature, after column chromatography, obtain position, gulf gold and replace perylene diimides derivative.
CN201410456992.9A 2014-09-10 2014-09-10 Position, a kind of gulf gold replaces perylene diimides derivative Expired - Fee Related CN104262396B (en)

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CN105842287A (en) * 2016-03-16 2016-08-10 济南市农业科学研究院 Nanomaterials used for detecting nitrogen dioxide and gas-sensitive sensor element
CN109053741A (en) * 2018-07-10 2018-12-21 南京林业大学 A kind of preparation method and application of imidodicarbonic diamide class pH fluorescence probe
CN111596524A (en) * 2019-02-21 2020-08-28 东友精细化工有限公司 Self-luminous photosensitive composition, color conversion layer, color filter and image display device
CN113248503A (en) * 2021-06-04 2021-08-13 陕西师范大学 Perylene diimide shoulder tetra-substituted derivative and preparation method and application thereof
CN113666949A (en) * 2021-08-30 2021-11-19 陕西师范大学 Gold (III) complex-perylene diimide derivative and fluorescent sensing tube and tubular fluorescent sensor prepared from same

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105842287A (en) * 2016-03-16 2016-08-10 济南市农业科学研究院 Nanomaterials used for detecting nitrogen dioxide and gas-sensitive sensor element
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CN109053741A (en) * 2018-07-10 2018-12-21 南京林业大学 A kind of preparation method and application of imidodicarbonic diamide class pH fluorescence probe
CN109053741B (en) * 2018-07-10 2021-03-19 南京林业大学 Preparation method and application of perylene diimide pH fluorescent probe
CN111596524A (en) * 2019-02-21 2020-08-28 东友精细化工有限公司 Self-luminous photosensitive composition, color conversion layer, color filter and image display device
CN111596524B (en) * 2019-02-21 2024-01-30 东友精细化工有限公司 Self-luminous photosensitive composition, color conversion layer, color filter and image display device
CN113248503A (en) * 2021-06-04 2021-08-13 陕西师范大学 Perylene diimide shoulder tetra-substituted derivative and preparation method and application thereof
CN113666949A (en) * 2021-08-30 2021-11-19 陕西师范大学 Gold (III) complex-perylene diimide derivative and fluorescent sensing tube and tubular fluorescent sensor prepared from same
CN113666949B (en) * 2021-08-30 2022-07-12 陕西师范大学 Gold (III) complex-perylene diimide derivative and fluorescent sensing tube and tubular fluorescent sensor prepared from same

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