CN110396113A - A kind of preparation method of red fluorescence silane coupling agent - Google Patents
A kind of preparation method of red fluorescence silane coupling agent Download PDFInfo
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- CN110396113A CN110396113A CN201810379811.5A CN201810379811A CN110396113A CN 110396113 A CN110396113 A CN 110396113A CN 201810379811 A CN201810379811 A CN 201810379811A CN 110396113 A CN110396113 A CN 110396113A
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- 239000006087 Silane Coupling Agent Substances 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 22
- 229910052693 Europium Inorganic materials 0.000 claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 13
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 13
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 10
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- -1 separation condition Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000013110 organic ligand Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000010668 complexation reaction Methods 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 3
- 230000006870 function Effects 0.000 abstract description 2
- 206010070834 Sensitisation Diseases 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 abstract 1
- 239000003550 marker Substances 0.000 abstract 1
- 230000008313 sensitization Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 229960000935 dehydrated alcohol Drugs 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- 150000002910 rare earth metals Chemical class 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VFKZTMPDYBFSTM-KVTDHHQDSA-N Mitobronitol Chemical compound BrC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-KVTDHHQDSA-N 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The invention discloses a kind of preparation methods of red fluorescence silane coupling agent, both have fluorescent functional, exist simultaneously hydrolysis key function, and chemical expression is Eu (DBM-Si)3.Eu indicates rare earth elements europium；Ligand is dibenzoyl methane (DBM)；The chemical expression of beta-diketon one type of silane coupling agent is DBM-Si, and Si indicates silane coupling agent.It is raw material using DBM, isocyano group silane coupling agent (ICPTES), optimum synthesis condition improves yield to 90%, isolates and purifies using silica gel column chromatography, obtain beta-diketon one type of silane coupling agent (DBM-Si).Sensitization chelating rare earth ion has excellent fluorescence property after coordination, is prepared into red fluorescence silane coupling agent, inspires 610 nm feature red fluorescence of europium ion in 394 nm.Simplification of flowsheet of the present invention improves purity, yield, has silane coupling agent specific functional, is widely used in fluorescent marker field.
Description
Technical field
The present invention relates to a kind of red fluorescence silane coupling agent synthesis conditions, the method for separation condition, specifically relate to
And a kind of silane coupling agent with rare earth coordination function.
Background technique
Recently, rare earth composite material is due to its excellent optical property, display technology, optical detection, it is biomedical at
Extensive research has been carried out in picture and fluorescence or laser system.But the special physicochemical property of rare earth ion, cause its compared with
Low fluorescence intensity and thermal stability.So Chang Liyong beta-diketon class rare earth organic ligand carries out chelating ligands to rare earth ion,
And then it is sensitized the luminescent properties of rare earth ion.
The design, synthesis type of silane coupling agent are more various at present, and the preparation of functional silane coupling agent can be further
Meet demand, such as containing mercaptosilane coupling agents synthesis (CN 102875588A), the synthesis of silane coupler containing sulfur(CN 1931862A).In order to keep the silane coupling agent scope of application more extensive, the other end of silane coupling agent is constantly modified, β-is such as utilized
Diketone modifies mercaptosilane coupling agents(CN 10105022A).But the designed functional silane coupling agent synthesized is equal now
There are complex process, purifying technique lack, yield is indefinite the problems such as.
Red fluorescence silane coupling agent proposed by the invention is to be sensitized for beta-diketon with rare earth ion chelating ligands
Feature, and combine the broad applicability of silane coupling agent.The chemical expression of the beta-diketon one type of silane coupling agent is DBM-Si,
Organic ligand DBM indicates dibenzoyl methane；Si indicates silane coupling agent, such as: isocyanatopropyl triethoxysilane
(ICPTES).The process of beta-diketon one type of silane coupling agent synthesis is as shown in Figure 1.
Beta-diketon is the aobvious acidity in part, and due to the electrophilic inductive effect of double carbonyls, there is only on methine for beta-diketon
Hydrogen Energy is substituted and very active.Under the action of highly basic, the Hydrogen Energy on methine is formed new by stronger electrophilic reagent attack
Carbon-carbon bond.Specific electronic transfer process is as shown in Figure 2.
To the combined coefficient of invention red fluorescence silane coupling agent optimize, purification is improved using silica gel column chromatography
Technique optimizes reaction condition, its yield is made to reach 70-90%, and it is red in 394 nm to inspire 610 nm feature of rare-earth europium ion
Color fluorescence.Beta-diketon one type of silane coupling agent further with rare-earth ion coordination, successfully prepares red fluorescence silane coupling agent Eu
(DBM-Si)3, wherein Eu indicates rare earth elements europium (Eu), and corresponding fluorescence color is red.Its detailed process is as shown in Figure 3.
Summary of the invention
The synthesis optimizing and way of purification of a kind of red fluorescence silane coupling agent provided by the invention, specifically include following two
A step:
(1) using DBM, DBM and ICPTES as raw material, tetrahydrofuran (THF) is solvent, and NaH is catalyst, synthesizes L-Si.It utilizes
Silica gel column chromatography (eluant, eluent ratio is petroleum ether: ethyl acetate=12:1-17:1 V/V and 1:1-6:1 V/V) carrys out purification of samples.
By to reaction temperature (25-65 DEG C), the reaction time (2-10 h), reactant mol ratio (M DBM:M TESPIC =1:1-1:8)
Regulation；
(2) L-Si and rare earth ion (Eu3+) be coordinated, adjust appropriate pH, temperature and reaction time.It is prepared red glimmering
Light silane coupling agent.
Advantages of the present invention:
(1) synthesis of beta-diketon one type of silane coupling agent and purification condition are optimized in the present invention, and synthesis obtains purified monomer, are produced
Rate reaches 70-90%；
(2) present invention has successfully prepared the fluorescent silane coupling agent with red fluorescence characteristic, can inspire in 394 nm
610 nm feature red fluorescence of rare-earth europium ion.
Detailed description of the invention
The flow chart of Fig. 1 synthesis beta-diketon one type of silane coupling agent；The electronics that Fig. 2 synthesizes beta-diketon one type of silane coupling agent turns
Move procedure chart；Fig. 3 red fluorescence silane coupling agent preparation flow figure；Fig. 4 is the glimmering of prepared red fluorescence silane coupling agent
Light excites spectrogram (left side)；Fluorescent emission spectrogram (right side)；Interior view is the digital photograph before and after 365 nm burst of ultraviolel.
Specific embodiment
The present invention is further illustrated in combination with embodiment:
Embodiment 1
It weighs 1 mmol DBM and 1 mmol NaH is dissolved in 20 ml THF, 65 DEG C of 2 h of stirring.Molar ratio, which is slowly added dropwise, is
The ICPTES of 1:1 continues 25 DEG C of stirring 10h, rotates away solvent, utilizes silica gel column chromatography and eluant, eluent (petroleum ether: acetic acid second
Ester=12:1 V/V and 6:1 V/V) it isolates and purifies, vacuum drying obtains DBM-Si, and yield reaches 70%.Weigh 0.3 mmol
DBM-Si, which is dissolved in 10 ml dehydrated alcohols, obtains a liquid, 0.1 mmol Eu (NO3)3 It is dissolved in 3ml dehydrated alcohol and obtains b liquid.
After 10 min of a liquid ultrasonic disperse, b liquid is added dropwise in 50 DEG C, and adjusting pH using certain proportion ammonium hydroxide is 7 or so, is stirred
It is isolated and purified after mixing 1 h, obtains Eu (DBM-Si)3, 610 nm feature red fluorescence of rare-earth europium ion is inspired in 394 nm.
Embodiment 2
It weighs 1 mmol DBM and 1 mmol NaH is dissolved in 20 ml THF, 65 DEG C of 2 h of stirring.Molar ratio, which is slowly added dropwise, is
The ICPTES of 1:2 continues 35 DEG C of stirring 8h, rotates away solvent, utilizes silica gel column chromatography and eluant, eluent (petroleum ether: acetic acid second
Ester=13:1 V/V and 5:1 V/V) it isolates and purifies, vacuum drying obtains DBM-Si, and yield reaches 78%.Weigh 0.3 mmol
DBM-Si, which is dissolved in 10 ml dehydrated alcohols, obtains a liquid, 0.1 mmol Eu (NO3)3 It is dissolved in 3ml dehydrated alcohol and obtains b liquid.
After 10 min of a liquid ultrasonic disperse, b liquid is added dropwise in 50 DEG C, and adjusting pH using certain proportion ammonium hydroxide is 8 or so, is stirred
It is isolated and purified after mixing 2 h, obtains Eu (DBM-Si)3, 610 nm feature red fluorescence of rare-earth europium ion is inspired in 394 nm.
Embodiment 3
It weighs 1 mmol DBM and 1 mmol NaH is dissolved in 20 ml THF, 65 DEG C of 2 h of stirring.Molar ratio, which is slowly added dropwise, is
The ICPTES of 1:3 continues 45 DEG C of 6 h of stirring, rotates away solvent, utilize silica gel column chromatography and eluant, eluent (petroleum ether: acetic acid second
Ester=14:1 V/V and 4:1 V/V) it isolates and purifies, vacuum drying obtains DBM-Si, and yield reaches 82%.Weigh 0.3 mmol
DBM-Si, which is dissolved in 10 ml dehydrated alcohols, obtains a liquid, 0.1 mmol Eu (NO3)3 It is dissolved in 3ml dehydrated alcohol and obtains b liquid.
After 10 min of a liquid ultrasonic disperse, b liquid is added dropwise in 50 DEG C, and adjusting pH using certain proportion ammonium hydroxide is 9 or so, is stirred
It is isolated and purified after mixing 3 h, obtains Eu (DBM-Si)3, 610 nm feature red fluorescence of rare-earth europium ion is inspired in 394 nm.
Embodiment 4
It weighs 1 mmol DBM and 1 mmol NaH is dissolved in 20 ml THF, 65 DEG C of 2 h of stirring.Molar ratio, which is slowly added dropwise, is
The ICPTES of 1:5 continues 55 DEG C of 6 h of stirring, rotates away solvent, utilize silica gel column chromatography and eluant, eluent (petroleum ether: acetic acid second
Ester=15:1 V/V and 3:1 V/V) it isolates and purifies, vacuum drying obtains DBM-Si, and yield reaches 86%.Weigh 0.3 mmol
DBM-Si, which is dissolved in 10 ml dehydrated alcohols, obtains a liquid, 0.1 mmol Eu (NO3)3 It is dissolved in 3ml dehydrated alcohol and obtains b liquid.
After 10 min of a liquid ultrasonic disperse, b liquid is added dropwise in 50 DEG C, and adjusting pH using certain proportion ammonium hydroxide is 9 or so, is stirred
It is isolated and purified after mixing 1 h, obtains Eu (DBM-Si)3, 610 nm feature red fluorescence of rare-earth europium ion is inspired in 394 nm.
Embodiment 5
It weighs 1 mmol DBM and 1 mmol NaH is dissolved in 20 ml THF, 65 DEG C of 2 h of stirring.Molar ratio, which is slowly added dropwise, is
The ICPTES of 1:8 continues 65 DEG C of 4 h of stirring, rotates away solvent, utilize silica gel column chromatography and eluant, eluent (petroleum ether: acetic acid second
Ester=16:1 V/V and 2:1 V/V) it isolates and purifies, vacuum drying obtains DBM-Si, and yield reaches 90%.Weigh 0.3 mmol
DBM-Si, which is dissolved in 10 ml dehydrated alcohols, obtains a liquid, 0.1 mmol Eu (NO3)3 It is dissolved in 3ml dehydrated alcohol and obtains b liquid.
After 10 min of a liquid ultrasonic disperse, b liquid is added dropwise in 50 DEG C, and adjusting pH using certain proportion ammonium hydroxide is 8 or so, is stirred
It is isolated and purified after mixing 2 h, obtains Eu (DBM-Si)3, 610 nm feature red fluorescence of rare-earth europium ion is inspired in 394 nm.
Claims (2)
1. a kind of method of synthesis condition of red fluorescence silane coupling agent, separation condition, chemical general formula are expressed as Eu (DBM-
Si)3, wherein Eu indicates rare earth elements europium (Eu), and DBM indicates that dibenzoyl methane, DBM-Si indicate the coupling of beta-diketon one type of silane
Agent；Specific preparation process is as follows: organic ligand (DBM) and silane coupling agent (ICPTES) are raw material, and THF is solvent, and NaH is to urge
Agent, by reaction temperature (25-65 DEG C), the reaction time (2-10 h), reactant mol ratio (M DBM:M TESPIC =1:1-
Regulation 1:8), synthesis obtains beta-diketon one type of silane coupling agent (DBM-Si), and uses silica gel column chromatography separating purification；By DBM-
Si and Eu (NO3)3It is each configured to certain density ethanol solution, using the mol ratio of DBM-Si and Eu ion, in certain temperature
Complexation reaction occurs within the scope of degree and appropriate pH, red fluorescence silane coupling agent Eu (DBM-Si is made after washing, drying
)3, 610 nm feature red fluorescence of rare-earth europium ion is inspired in 394 nm.
2. a kind of preparation method of red fluorescence silane coupling agent as described in claim 1:
(1) rare earth element uses europium (Eu)；Beta-diketon class organic ligand uses dibenzoyl methane (DBM)；Silane coupling agent makes
With isocyanatopropyl triethoxysilane (ICPTES)；
(2) synthesizing the temperature controlling range of beta-diketon one type of silane coupling agent (DBM-Si) is 25-65 DEG C, and reaction time range is 2-
10h, reactant mol ratio range areM DBM:M TESPIC =1:1-1:8；Pass through silica gel column chromatography separating purification, eluant, eluent ratio
Range is petroleum ether: ethyl acetate=12:1-17:1 V/V and 1:1-6:1 V/V；Synthesis obtains the production of beta-diketon one type of silane coupling agent
Rate reaches 70-90%；
(3) red fluorescence silane coupling agent (Eu (DBM-Si) is prepared3) pH scope control in 7-9 or so, reaction temperature control exists
40-60 DEG C, the reaction time controls in 1-3 h.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5316909A (en) * | 1991-03-15 | 1994-05-31 | Wallac Oy | Method for increasing fluorescence |
| CN101220266A (en) * | 2008-01-24 | 2008-07-16 | 同济大学 | Process for producing beta-diketone functionalization rare earth mesoporous hybridisation luminescent material |
| CN102002359A (en) * | 2010-11-17 | 2011-04-06 | 同济大学 | Method for preparing beta-diketone functional rare-earth organic luminous gel based on silicon-boron composite network |
| CN102618260A (en) * | 2012-03-14 | 2012-08-01 | 同济大学 | Method for preparing carbon nano tube/silica network/ligand/rare-earth organic and inorganic composite luminescent material |
| US20130231468A1 (en) * | 2010-11-22 | 2013-09-05 | Takeshi Yamashita | Rare earth metal complex |
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-
2018
- 2018-04-25 CN CN201810379811.5A patent/CN110396113A/en active Pending
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|---|---|---|---|---|
| US5316909A (en) * | 1991-03-15 | 1994-05-31 | Wallac Oy | Method for increasing fluorescence |
| CN101220266A (en) * | 2008-01-24 | 2008-07-16 | 同济大学 | Process for producing beta-diketone functionalization rare earth mesoporous hybridisation luminescent material |
| CN102002359A (en) * | 2010-11-17 | 2011-04-06 | 同济大学 | Method for preparing beta-diketone functional rare-earth organic luminous gel based on silicon-boron composite network |
| US20130231468A1 (en) * | 2010-11-22 | 2013-09-05 | Takeshi Yamashita | Rare earth metal complex |
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Application publication date: 20191101 |
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