CN110105786A - A kind of crocic acid cyanine dyes and its application - Google Patents
A kind of crocic acid cyanine dyes and its application Download PDFInfo
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- CN110105786A CN110105786A CN201910376058.9A CN201910376058A CN110105786A CN 110105786 A CN110105786 A CN 110105786A CN 201910376058 A CN201910376058 A CN 201910376058A CN 110105786 A CN110105786 A CN 110105786A
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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Abstract
The invention discloses a kind of crocic acid cyanine dyes and its applications, crocic acid cyanine dyes belongs to one kind of cyanine dyes, it is condensed by crocic acid and the group with electron supplying capacity, its primary structure is arranged to make up by supplied for electronic-electrophilic-electron-donating group, there is strong and sharp absorption peak near infrared region, there is good photo and thermal stability and aggregation luminescent properties.Crocic acid cyanine dyes in the present invention, can be used as crosslinking agent, for synthesizing visualization light-induced shape-memory polymer.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of crocic acid cyanine dyes and its application.
Background technique
Crosslinking agent is also referred to as bridging agent, is the important component of poly- hydro carbons photoresist, this photoresist
Photochemical solidification effect, dependent on the crosslinking agent participation reaction for having double photonasty functional groups, generation is double certainly after crosslinking agent exposure
By base, it and poly- hydrocarbon resins phase separation form bridged bond between polymer molecular chain, become the insoluble object of three-dimensional structure
Matter.Crosslinking agent is used primarily in high molecular material (rubber and thermosetting resin).Because the molecular structure of high molecular material just as
The long line of one rule, intensity is low when not being crosslinked, and easily breaks, and without elasticity, the effect of crosslinking agent be exactly line style molecule it
Between generate chemical bond, be connected with each other linear molecule, formed reticular structure.
Organic functions dyestuff is in optical fields such as optical transition, solar battery, optical data storages, while in biomolecule
The medicine such as label, fluorescence detection, anticancer agent direction extensive application value, but be used as crosslinking agent there are no relevant notes
Record.
Summary of the invention
In view of the above-mentioned problems, the present invention is intended to provide a kind of crocic acid cyanine dyes, the crocic acid cyanine dyes structural formula is such as
Under:
Preferably, the preparation of the crocic acid cyanine dyes, includes the following steps:
1) 2- thienyl mercaptan and 4- piperidine methyl formate are taken according to molar ratio 1:1.4-1.7, dissolved with toluene and mixed
It is even, it vacuumizes, stirs, 115-125 DEG C of back flow reaction 2-4h, it is after the reaction was completed, cooling, solvent is dried and removed, crude product is obtained
I, the petroleum ether and ethyl acetate for being 9-11:1 with volume ratio dissolve crude product I, isolated 1- thiophene -2-piperidinecarboxylic acid first
Ester；
2) 1- thiophene -2-piperidinecarboxylic acid methyl esters and sodium hydroxide are taken according to molar ratio 1:2.7-2.8, and is gone with 24-44mL
Ionized water is dissolved and is uniformly mixed, stirring, 100-110 DEG C of back flow reaction 2-4h, after the reaction was completed, cooling, adjusts pH to 2-3,
It is filtered under diminished pressure, took filter solid, be dried in vacuo, obtain -2 piperidinecarboxylic acid of 1- thiophene；
3) according to molar ratio 1:1.2:1.5-2:0.05-0.1 take -2 piperidinecarboxylic acid of 1- thiophene, hydroxyethyl methacrylate,
N, N- diisopropylcarbodiimide and 4-dimethylaminopyridine, are dissolved and are uniformly mixed with dry methylene chloride, are vacuumized, and are stirred
It mixes, 115-125 DEG C of back flow reaction 2-4h, after the reaction was completed, repetition is filtered under diminished pressure, until without suspended particulate in filtrate, it is dry, it obtains
To crude product II, the petroleum ether and ethyl acetate for being 15:1 with volume ratio dissolve crude product II, are filtered under diminished pressure, isolated 1- thiophene
- 2 piperidines -4- formic acid of pheno-methacrylate -2- hydroxyethyl ester, dry methylene chloride refers to anhydrous methylene chloride, colourless
Bright volatile liquid；
4) crocic acid and 1- thiophene -2 piperidines -4- formic acid-methacrylate -2- hydroxyl second are taken according to molar ratio 1:2-2.5
Toluene/n-Butanol soluble that base ester is 1:1 with volume ratio is simultaneously uniformly mixed, and is vacuumized, and is stirred, 115-125 DEG C of back flow reaction 1-
2h, it is after the reaction was completed, cooling, solvent is dried and removed, crude product is washed with methanol, is filtered under diminished pressure, obtains black solid crocic acid cyanines
Dyestuff.
The step of more preferably preparing crocic acid cyanine dyes is as follows:
1) 2- thienyl mercaptan and 4- piperidine methyl formate are taken according to molar ratio 1:1.4-1.7, dissolved with toluene and mixed
It is even, it vacuumizes, magnetic agitation, nitrogen protection, 120 DEG C of back flow reaction 3h are cooled to room temperature after the reaction was completed, and revolving removes molten
Agent, obtains crude product I, and petroleum ether in a volume ratio of 10:1 and ethyl acetate dissolution crude product I are obtained through column chromatography for separation
1- thiophene -2-piperidinecarboxylic acid methyl esters；
2) 1- thiophene -2-piperidinecarboxylic acid methyl esters and sodium hydroxide are taken according to molar ratio 1:2.7-2.8, and is gone with 24-44mL
Ionized water is dissolved and is uniformly mixed, magnetic agitation, and 105 DEG C of back flow reaction 3h are cooled to room temperature after the reaction was completed, with 10% second
Aqueous acid adjusts pH to 2-3, is filtered under diminished pressure, took filter solid, is dried in vacuo, obtains -2 piperidinecarboxylic acid of 1- thiophene；
3) according to molar ratio 1:1.2:1.5-2:0.05-0.1 take -2 piperidinecarboxylic acid of 1- thiophene, hydroxyethyl methacrylate,
N, N- diisopropylcarbodiimide and 4-dimethylaminopyridine, are dissolved and are uniformly mixed with dry methylene chloride, are vacuumized, magnetic force
Stirring, nitrogen protection, 120 DEG C of back flow reaction 3h, after the reaction was completed, repetition are filtered under diminished pressure, until without suspended particulate, rotation in filtrate
Solvent is steamed, crude product II is obtained, the petroleum ether and ethyl acetate for being 15:1 with volume ratio dissolve crude product II, are filtered under diminished pressure, will
Filtrate column chromatography, isolated -2 piperidines -4- formic acid of 1- thiophene-methacrylate -2- hydroxyethyl ester；
4) crocic acid and 1- thiophene -2 piperidines -4- formic acid-methacrylate -2- hydroxyl second are taken according to molar ratio 1:2-2.5
Base ester is dissolved and is uniformly mixed with toluene/n-butanol (v/v=1:1), vacuumized, magnetic agitation, nitrogen protection, 120 DEG C of reflux
Reaction 1h is cooled to room temperature after the reaction was completed, and revolving removes solvent, is washed crude product 2-3 times with methanol, is filtered under diminished pressure, obtains black
Color solid crocic acid cyanine dyes.
Crocic acid cyanine dyes in the present invention is named as crocic acid cyanine dyes YHD795, be can be used as crosslinking agent, is used for
Synthesis visualization light-induced shape-memory polymer.
The aggregation principle of luminosity of YHD795 is aggregation-induced emission (AIE): crocic acid cyanine dyes is by pentacyclic gram of ketone
Acid is condensed with electron-donating group, and primary structure is arranged to make up by supplied for electronic-electrophilic-electron-donating group；At single point
It under sub- state, is connected between intramolecular chromophore by carbon-carbon single bond, the ability of Internal Rotations of Molecules with higher, electronics is in illumination
Excitation state is energized into from ground state afterwards returns the energy that ground state is distributed consumed by internal molecular motion；And the intramolecular after aggregation
Movement is restricted, and chromophore can only carry out Internal Rotations of Molecules by a small margin, so that electronics returns to the energy conversion that ground state is distributed
It is distributed for radiation, shows as fluorescent emission.Beneficial effects of the present invention:
Crocic acid cyanine dyes of the invention has strong and sharp absorption peak near infrared region, and there is good photo-thermal to stablize
Property and aggregation luminescent properties.
Detailed description of the invention
Fig. 1 crocic acid cyanine dyes infrared spectrogram, abscissa refer to wavelength.
Specific embodiment
Technical effect in order to further illustrate the present invention is specifically described the present invention below by embodiment.
Embodiment 1
1) 2- thienyl mercaptan and 4- piperidine methyl formate are taken according to molar ratio 1:1.4, is dissolved and is uniformly mixed with toluene, taken out
Vacuum, magnetic agitation, nitrogen protection, 120 DEG C of back flow reaction 3h are cooled to room temperature after the reaction was completed, and revolving removes solvent, are obtained
To crude product I, the petroleum ether for being 10:1 with mass ratio and ethyl acetate dissolve crude product I and obtain 1- thiophene through column chromatography for separation
Pheno -2-piperidinecarboxylic acid methyl esters；
2) 1- thiophene -2-piperidinecarboxylic acid methyl esters and sodium hydroxide are taken according to molar ratio 1-2.8, and water-soluble with 24mL deionization
It solves and is uniformly mixed, magnetic agitation, 105 DEG C of back flow reaction 3h are cooled to room temperature after the reaction was completed, with 10% acetic acid aqueous solution
PH to 2 is adjusted, is filtered under diminished pressure, took filter solid, is dried in vacuo, obtains -2 piperidinecarboxylic acid of 1- thiophene；
3) -2 piperidinecarboxylic acid of 1- thiophene, hydroxyethyl methacrylate, N, N- bis- are taken according to molar ratio 1:1.2:1.5:0.05
Diisopropylcarbodiimide and 4-dimethylaminopyridine, are dissolved and are uniformly mixed with dry methylene chloride, are vacuumized, magnetic agitation,
Nitrogen protection, 120 DEG C of back flow reaction 3h, after the reaction was completed, repetition are filtered under diminished pressure, until rotating molten in filtrate without suspended particulate
Agent obtains crude product II, and the petroleum ether and ethyl acetate for being 15:1 with mass ratio dissolve crude product II, is filtered under diminished pressure, by filtrate
Column chromatography, isolated -2 piperidines -4- formic acid of 1- thiophene-methacrylate -2- hydroxyethyl ester；
4) crocic acid and 1- thiophene -2 piperidines -4- formic acid-methacrylate -2- hydroxyethyl ester are taken according to molar ratio 1:2,
It is dissolved and is uniformly mixed with toluene/n-butanol (v/v=1:1), vacuumized, magnetic agitation, nitrogen protection, 120 DEG C of back flow reactions
1h is cooled to room temperature after the reaction was completed, and revolving removes solvent, washes crude product 2-3 times with methanol, is filtered under diminished pressure, and it is solid to obtain black
Body crocic acid cyanine dyes, yield 49.36%.
Embodiment 2
1) 2- thienyl mercaptan and 4- piperidine methyl formate are taken according to molar ratio 1:1.55, are dissolved and is uniformly mixed with toluene,
It vacuumizing, magnetic agitation, nitrogen protection, 120 DEG C of back flow reaction 3h are cooled to room temperature after the reaction was completed, and revolving removes solvent,
Crude product I is obtained, the petroleum ether for being 10:1 with mass ratio and ethyl acetate dissolve crude product I and obtains 1- thiophene through column chromatography for separation
Pheno -2-piperidinecarboxylic acid methyl esters；
2) 1- thiophene -2-piperidinecarboxylic acid methyl esters and sodium hydroxide are taken according to molar ratio 1:2.75, and with 34mL deionized water
It dissolves and is uniformly mixed, magnetic agitation, 105 DEG C of back flow reaction 3h are cooled to room temperature after the reaction was completed, water-soluble with 10% acetic acid
Liquid adjusts pH to 2.5, is filtered under diminished pressure, took filter solid, is dried in vacuo, obtains -2 piperidinecarboxylic acid of 1- thiophene；
3) -2 piperidinecarboxylic acid of 1- thiophene, hydroxyethyl methacrylate, N, N- bis- are taken according to molar ratio 1:1.2:1.75:0.07
Diisopropylcarbodiimide and 4-dimethylaminopyridine, are dissolved and are uniformly mixed with dry methylene chloride, are vacuumized, magnetic agitation,
Nitrogen protection, 120 DEG C of back flow reaction 3h, after the reaction was completed, repetition are filtered under diminished pressure, until rotating molten in filtrate without suspended particulate
Agent obtains crude product II, and the petroleum ether and ethyl acetate for being 15:1 with mass ratio dissolve crude product II, is filtered under diminished pressure, by filtrate
Column chromatography, isolated -2 piperidines -4- formic acid of 1- thiophene-methacrylate -2- hydroxyethyl ester；
4) crocic acid and 1- thiophene -2 piperidines -4- formic acid-methacrylate -2- ethoxy are taken according to molar ratio 1:2.25
Ester is dissolved and is uniformly mixed with toluene/n-butanol (v/v=1:1), vacuumized, magnetic agitation, nitrogen protection, and 120 DEG C of reflux are anti-
Answer 1h, after the reaction was completed, be cooled to room temperature, revolving removes solvent, washes crude product 2-3 times with methanol, is filtered under diminished pressure, obtains black
Solid crocic acid cyanine dyes, yield 35.91%.
Embodiment 3
1) 2- thienyl mercaptan and 4- piperidine methyl formate are taken according to molar ratio 1:1.7, is dissolved and is uniformly mixed with toluene, taken out
Vacuum, magnetic agitation, nitrogen protection, 120 DEG C of back flow reaction 3h are cooled to room temperature after the reaction was completed, and revolving removes solvent, are obtained
To crude product I, the petroleum ether for being 10:1 with mass ratio and ethyl acetate dissolve crude product I and obtain 1- thiophene through column chromatography for separation
Pheno -2-piperidinecarboxylic acid methyl esters；
2) 1- thiophene -2-piperidinecarboxylic acid methyl esters and sodium hydroxide are taken according to molar ratio 1:2.8, and water-soluble with 44mL deionization
It solves and is uniformly mixed, magnetic agitation, 105 DEG C of back flow reaction 3h are cooled to room temperature after the reaction was completed, with 10% acetic acid aqueous solution
PH to 3 is adjusted, is filtered under diminished pressure, took filter solid, is dried in vacuo, obtains -2 piperidinecarboxylic acid of 1- thiophene；
3) -2 piperidinecarboxylic acid of 1- thiophene, hydroxyethyl methacrylate, N, N- diisopropyl are taken according to molar ratio 1:1.2:2:0.1
Base carbodiimide and 4-dimethylaminopyridine, are dissolved and are uniformly mixed with dry methylene chloride, are vacuumized, magnetic agitation, nitrogen
Protection, 120 DEG C of back flow reaction 3h, after the reaction was completed, repetition are filtered under diminished pressure, until rotating solvent without suspended particulate in filtrate, obtaining
To crude product II, the petroleum ether and ethyl acetate for being 15:1 with mass ratio dissolve crude product II, are filtered under diminished pressure, by filtrate column layer
Analysis, isolated -2 piperidines -4- formic acid of 1- thiophene-methacrylate -2- hydroxyethyl ester；
4) crocic acid and 1- thiophene -2 piperidines -4- formic acid-methacrylate -2- ethoxy are taken according to molar ratio 1:2.5
Ester is dissolved and is uniformly mixed with toluene/n-butanol (v/v=1:1), vacuumized, magnetic agitation, nitrogen protection, and 120 DEG C of reflux are anti-
Answer 1h, after the reaction was completed, be cooled to room temperature, revolving removes solvent, washes crude product 2-3 times with methanol, is filtered under diminished pressure, obtains black
Solid crocic acid cyanine dyes, yield 60.05%.
Finally, it should be noted that the above examples are only used to illustrate the technical scheme of the present invention rather than limits, although ginseng
Technical solution of the present invention is described in detail according to preferred embodiment, it will be appreciated by those skilled in the art that can be to this
The technical solution of invention is modified or replaced equivalently, and without departing from the purpose and scope of the invention, should all be covered at this
In the protection scope of invention.
Claims (4)
1. a kind of crocic acid cyanine dyes, which is characterized in that structural formula is as follows:
。
2. a kind of method for preparing crocic acid cyanine dyes as described in claim 1, which comprises the steps of:
1) 2- thienyl mercaptan and 4- piperidine methyl formate are taken according to molar ratio 1:1.4-1.7, is dissolved and is uniformly mixed with toluene, taken out
Vacuum, stirring, 115-125 DEG C of back flow reaction 2-4h is after the reaction was completed, cooling, dries and removes solvent, obtains crude product I, use body
Product dissolves crude product I, isolated 1- thiophene -2-piperidinecarboxylic acid methyl esters than the petroleum ether and ethyl acetate for being 9-11:1；
2) 1- thiophene -2-piperidinecarboxylic acid methyl esters and sodium hydroxide are taken according to molar ratio 1:2.7-2.8, and simultaneously with deionized water dissolving
It is uniformly mixed, stirring, 100-110 DEG C of back flow reaction 2-4h, it is after the reaction was completed, cooling, pH to 2-3 is adjusted, is filtered under diminished pressure, took
Filter solid, vacuum drying, obtains -2 piperidinecarboxylic acid of 1- thiophene；
3) -2 piperidinecarboxylic acid of 1- thiophene, hydroxyethyl methacrylate, N, N- are taken according to molar ratio 1:1.2:1.5-2:0.05-0.1
Diisopropylcarbodiimide and 4-dimethylaminopyridine, are dissolved and are uniformly mixed with dry methylene chloride, are vacuumized, stirring,
115-125 DEG C of back flow reaction 2-4h, after the reaction was completed, repetition are filtered under diminished pressure, until without suspended particulate in filtrate, it is dry, it obtains
Crude product II, the petroleum ether and ethyl acetate for being 15:1 with volume ratio dissolve crude product II, are filtered under diminished pressure, isolated 1- thiophene
- 2 piperidines -4- formic acid of pheno-methacrylate -2- hydroxyethyl ester；
4) crocic acid and 1- thiophene -2 piperidines -4- formic acid-methacrylate -2- hydroxyethyl ester are taken according to molar ratio 1:2-2.5,
Toluene/the n-Butanol soluble for being 1:1 with volume ratio is simultaneously uniformly mixed, and is vacuumized, stirring, 115-125 DEG C of back flow reaction 1-2h, instead
It is cooling after the completion of answering, solvent is dried and removed, crude product is washed with methanol, is filtered under diminished pressure, obtains black solid crocic acid cyanine dyes.
3. the application of the crocic acid cyanine dyes as described in any right of claim 1-2.
4. using including: that can be used as crosslinking agent described in claim 3, for synthesizing visualization light-induced shape-memory polymer.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111040060A (en) * | 2019-12-27 | 2020-04-21 | 苏州大学 | Method for polymerizing 'active' free radical of vinyl monomer under near-infrared photo-thermal conversion |
| CN111848596A (en) * | 2020-07-27 | 2020-10-30 | 上海大学 | Near-infrared light stimulus response type functional macromolecule and intelligent nano material and preparation method thereof |
| CN115010850A (en) * | 2022-06-08 | 2022-09-06 | 上海大学 | Near-infrared photo-thermal polymer functional material with cross-linked stable structure, preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1989015A (en) * | 2004-07-15 | 2007-06-27 | 惠普开发有限公司 | Compositions, systems and methods for imaging |
| CN105733504A (en) * | 2016-02-04 | 2016-07-06 | 东南大学 | Near-infrared wave-absorbing material having liquid-crystal properties |
| CN107365401A (en) * | 2017-06-15 | 2017-11-21 | 东南大学 | A kind of near-infrared response backbone chain type liquid crystal elastomer and preparation method thereof |
-
2019
- 2019-05-07 CN CN201910376058.9A patent/CN110105786A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1989015A (en) * | 2004-07-15 | 2007-06-27 | 惠普开发有限公司 | Compositions, systems and methods for imaging |
| CN105733504A (en) * | 2016-02-04 | 2016-07-06 | 东南大学 | Near-infrared wave-absorbing material having liquid-crystal properties |
| CN107365401A (en) * | 2017-06-15 | 2017-11-21 | 东南大学 | A kind of near-infrared response backbone chain type liquid crystal elastomer and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 橡胶工业原材料与装备简明手册编审委员会编著: "《橡胶工业原材料与装备简明手册（2016年版）》", 31 December 2016, 北京理工大学出版社 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111040060A (en) * | 2019-12-27 | 2020-04-21 | 苏州大学 | Method for polymerizing 'active' free radical of vinyl monomer under near-infrared photo-thermal conversion |
| CN111040060B (en) * | 2019-12-27 | 2020-12-29 | 苏州大学 | Method for polymerizing 'active' free radical of vinyl monomer under near-infrared photo-thermal conversion |
| CN111848596A (en) * | 2020-07-27 | 2020-10-30 | 上海大学 | Near-infrared light stimulus response type functional macromolecule and intelligent nano material and preparation method thereof |
| CN115010850A (en) * | 2022-06-08 | 2022-09-06 | 上海大学 | Near-infrared photo-thermal polymer functional material with cross-linked stable structure, preparation method and application thereof |
| CN115010850B (en) * | 2022-06-08 | 2023-09-15 | 上海大学 | Near-infrared photo-thermal polymer functional material with cross-linked stable structure, preparation method and application thereof |
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Application publication date: 20190809 |