CN113754560A - Preparation method of salicylaldehyde-based fluorescent compound - Google Patents
Preparation method of salicylaldehyde-based fluorescent compound Download PDFInfo
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- CN113754560A CN113754560A CN202010489713.4A CN202010489713A CN113754560A CN 113754560 A CN113754560 A CN 113754560A CN 202010489713 A CN202010489713 A CN 202010489713A CN 113754560 A CN113754560 A CN 113754560A
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- salicylaldehyde
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- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 63
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000010992 reflux Methods 0.000 claims abstract description 22
- 238000005406 washing Methods 0.000 claims abstract description 22
- MYUNWHTZYXUCIK-WEVVVXLNSA-N 2-[(E)-hydrazinylidenemethyl]phenol Chemical compound N\N=C\C1=CC=CC=C1O MYUNWHTZYXUCIK-WEVVVXLNSA-N 0.000 claims abstract description 20
- 238000001035 drying Methods 0.000 claims abstract description 20
- 238000001914 filtration Methods 0.000 claims abstract description 20
- 238000010438 heat treatment Methods 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 15
- 235000019441 ethanol Nutrition 0.000 claims abstract description 14
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 13
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000005457 ice water Substances 0.000 claims abstract description 10
- 239000002244 precipitate Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 3
- 229940125904 compound 1 Drugs 0.000 claims description 14
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 229930014626 natural product Natural products 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002262 Schiff base Substances 0.000 abstract description 2
- 150000004753 Schiff bases Chemical class 0.000 abstract description 2
- 239000000126 substance Substances 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000012984 biological imaging Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 description 1
- 229960002529 benzbromarone Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
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- 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
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of a salicylaldehyde-based fluorescent compound. The invention utilizes the characteristic of the reaction of natural products and Schiff base, and the prepared fluorescent compound has good biocompatibility, is not easy to dissolve in water, and has orange (or yellow) fluorescence emission in a solid state. The method comprises the following steps: (1) dissolving 40-80 mmol of hydrazine hydrate (mass fraction 85%) in 10-20 ml of absolute ethyl alcohol according to a molar volume ratio, heating to 60-70 ℃, slowly dropwise adding 40mmol of salicylaldehyde into a reaction container under the condition of continuous stirring, refluxing for 2-3 h, filtering while hot to obtain yellow powdery solid, washing with absolute ethyl alcohol, and drying to obtain salicylaldehyde hydrazone; (2) dissolving salicylaldehyde hydrazone and 20-30 mmol 1, 4-benzaldehyde in 20-30 ml DMF according to a molar volume ratio, adding 0.8-1.2 ml acetic acid as a catalyst, heating and refluxing for 4-6 h, crystallizing in an ice water bath, filtering to obtain a precipitate, washing with ethanol for three times, and drying to obtain the fluorescent compound 1. The raw materials used in the invention are low in price and environment-friendly, and the yield of the prepared fluorescent compound is up to 58-72%.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of a salicylaldehyde-based fluorescent compound.
Background
Salicylaldehyde is a natural product of colorless to yellow oily liquid, can be used as a spice, a food additive and the like, can be used as an organic synthesis intermediate with extremely wide application, and is commonly used for synthesizing gypenzine, benzbromarone, acetominophenidone and the like in the synthesis of medicaments. The aldehyde group in the salicylaldehyde is an important functional group in organic synthesis, can react with amino to increase the length of a carbon chain, introduces a carbon-nitrogen double bond with bioactivity, can expand a conjugated system of the salicylaldehyde through the reaction, and expands the application of the salicylaldehyde in other fields.
Aggregation-induced emission (AIE) was proposed in 2001 by tangzhizhong et al, which solves the problem of aggregation-induced quenching of the conventional fluorescent materials, has stable chemical properties, very strong fluorescence in high water content, strong environmental adaptability, and excellent application prospects in the fluorescence detection field, can realize very sensitive detection of heavy metals and the like, and can also be applied to the related fields of biological imaging and the like. It is known that a fluorescent compound with a longer emission wavelength is more beneficial to biological imaging, and because the long emission wavelength has less photodamage to biological tissues and small interference to biological tissue autofluorescence, but at present, a fluorescent substance with a long emission wavelength is synthesized by complex chemical reactions, so that not only is the production cost high, but also due to the complex structure, the fluorescent substance has the disadvantages of high toxicity to biological tissues, poor biocompatibility and the like.
Disclosure of Invention
The invention aims to provide a preparation method of a fluorescent compound prepared by taking a natural product salicylaldehyde as a raw material, wherein the prepared fluorescent compound can emit orange or yellow fluorescence in a solid state.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a method for preparing a fluorescent compound by using a natural product salicylaldehyde as a raw material comprises the following steps:
(1) dissolving 40-80 mmol of hydrazine hydrate (mass fraction 85%) in 10-20 ml of absolute ethyl alcohol according to a molar volume ratio, heating to 60-70 ℃, slowly dropwise adding 40mmol of salicylaldehyde into a reaction container under the condition of continuous stirring, refluxing for 2-3 h, filtering while hot to obtain yellow powdery solid, washing with absolute ethyl alcohol, and drying to obtain salicylaldehyde hydrazone;
(2) dissolving salicylaldehyde hydrazone and 20-30 mmol 1, 4-benzaldehyde in 20-30 ml DMF according to a molar volume ratio, adding 0.8-1.2 ml acetic acid as a catalyst, heating and refluxing for 4-6 h, crystallizing in an ice water bath, filtering to obtain a precipitate, washing with ethanol for three times, and drying to obtain the fluorescent compound 1.
The salicylaldehyde, the hydrazine hydrate (the mass fraction is 85%) and the 1, 4-benzenedialdehyde are directly purchased by an alatin reagent company.
Preferably, in step (2), the residual ethanol is removed by vacuum drying after ethanol washing to obtain fluorescent compound 1.
The invention has the beneficial effects that:
(1) the used raw materials are low in price and environment-friendly;
(2) a simple and green synthesis path is used, so that the energy consumption is low;
(3) the yield of the fluorescent compound prepared by the invention is up to 58-72%;
(4) the invention utilizes the characteristic of the reaction of natural products and Schiff base, and the prepared fluorescent compound has good biocompatibility, is not easy to dissolve in water, and has orange (or yellow) fluorescence emission in a solid state.
Drawings
FIG. 1 is an infrared spectrum of a fluorescent compound 1 prepared according to the present invention, and the structures of the functional groups of the fluorescent compound 1 are determined.
FIG. 2 shows the NMR spectrum of fluorescent compound 1 prepared according to the present invention, and the structure of fluorescent compound 1 is determined.
FIG. 3 is a fluorescence spectrum of fluorescent compound 1 prepared according to the present invention, and it can be seen that the maximum excitation wavelength of fluorescent compound 1 is 410nm and the maximum emission wavelength is 580 nm.
Detailed Description
The first embodiment is as follows: dissolving 40mmol of hydrazine hydrate (85 mass percent) in 10ml of absolute ethyl alcohol, heating to 60 ℃, slowly dropwise adding 40mmol of salicylaldehyde into a reactor under the condition of continuous stirring, refluxing for 2 hours, filtering while hot to obtain yellow powdery solid, washing with absolute ethyl alcohol, putting into an oven for drying to obtain salicylaldehyde hydrazone, dissolving the obtained salicylaldehyde hydrazone and 30mmol of 1, 4-benzaldehyde in 30ml of DMF, adding 1.2ml of acetic acid as a catalyst, heating to 60 ℃, refluxing for 6 hours, crystallizing in an ice water bath, filtering to obtain precipitate, washing with ethanol for three times, and drying in vacuum to obtain a yellow powdery fluorescent compound 1 with the yield of 58%, wherein the fluorescent compound emits orange light under the irradiation of an ultraviolet lamp.
The second embodiment is as follows: dissolving 60mmol of hydrazine hydrate (85 mass percent) in 15ml of absolute ethyl alcohol, heating to 65 ℃, slowly dropwise adding 40mmol of salicylaldehyde into a reactor under the condition of continuous stirring, refluxing for 2.5 hours, filtering while hot to obtain a yellow powdery solid, washing with absolute ethyl alcohol, putting into an oven for drying to obtain salicylaldehyde hydrazone, dissolving the obtained salicylaldehyde hydrazone and 30mmol of 1, 4-benzaldehyde in 30ml of DMF, adding 1.2ml of acetic acid as a catalyst, heating to 60 ℃, refluxing for 6 hours, crystallizing in an ice water bath, filtering to obtain a precipitate, washing with ethanol for three times, drying in vacuum to obtain a yellow powdery fluorescent compound 1 with the yield of 60%, and emitting orange light by irradiating an ultraviolet lamp with the fluorescent compound.
The third concrete implementation mode: dissolving 80mmol of hydrazine hydrate (85 mass percent) in 20ml of absolute ethyl alcohol, heating to 70 ℃, slowly dripping 40mmol of salicylaldehyde into a reactor under the condition of continuous stirring, refluxing for 3 hours, filtering while the salicylaldehyde is hot to obtain yellow powdery solid, washing with the absolute ethyl alcohol, putting into an oven for drying to obtain salicylaldehyde hydrazone, dissolving the obtained salicylaldehyde hydrazone and 30mmol of 1, 4-benzaldehyde in 30ml of DMF, adding 1.2ml of acetic acid as a catalyst, heating to 60 ℃, refluxing for 6 hours, crystallizing in an ice water bath, filtering to obtain precipitate, washing with ethanol for three times, and drying in vacuum to obtain a yellow powdery fluorescent compound 1 with the yield of 63%, wherein the fluorescent compound emits orange light under the irradiation of an ultraviolet lamp.
The fourth concrete implementation mode: dissolving 40mmol of hydrazine hydrate (85 mass percent) in 10ml of absolute ethyl alcohol, heating to 60 ℃, slowly dropwise adding 40mmol of salicylaldehyde into a reactor under the condition of continuous stirring, refluxing for 2 hours, filtering while hot to obtain yellow powdery solid, washing with absolute ethyl alcohol, putting into an oven for drying to obtain salicylaldehyde hydrazone, dissolving the obtained salicylaldehyde hydrazone and 20mmol of 1, 4-benzaldehyde in 20ml of DMF, adding 0.8ml of acetic acid as a catalyst, heating to 60 ℃, refluxing for 4 hours, crystallizing in an ice water bath, filtering to obtain precipitate, washing with ethanol for three times, and drying in vacuum to obtain a yellow powdery fluorescent compound 1 with the yield of 65%, wherein the fluorescent compound emits orange light under the irradiation of an ultraviolet lamp.
The fifth concrete implementation mode: dissolving 60mmol of hydrazine hydrate (85 mass percent) in 15ml of absolute ethyl alcohol, heating to 65 ℃, slowly dropwise adding 40mmol of salicylaldehyde into a reactor under the condition of continuous stirring, refluxing for 2.5 hours, filtering while hot to obtain a yellow powdery solid, washing with absolute ethyl alcohol, putting into an oven for drying to obtain salicylaldehyde hydrazone, dissolving the obtained salicylaldehyde hydrazone and 20mmol of 1, 4-benzaldehyde in 20ml of DMF, adding 0.8ml of acetic acid as a catalyst, heating to 60 ℃, refluxing for 4 hours, crystallizing in an ice water bath, filtering to obtain a precipitate, washing with ethanol for three times, drying in vacuum to obtain a yellow powdery fluorescent compound 1, wherein the yield is 67%, and the fluorescent compound emits orange light under the irradiation of an ultraviolet lamp.
The sixth specific implementation mode: dissolving 80mmol of hydrazine hydrate (85 mass percent) in 20ml of absolute ethyl alcohol, heating to 70 ℃, slowly dripping 40mmol of salicylaldehyde into a reactor under the condition of continuous stirring, refluxing for 3 hours, filtering while the salicylaldehyde is hot to obtain yellow powdery solid, washing with the absolute ethyl alcohol, putting the yellow powdery solid into an oven for drying to obtain salicylaldehyde hydrazone, dissolving the obtained salicylaldehyde hydrazone and 20mmol of 1, 4-benzaldehyde in 20ml of DMF, adding 0.8ml of acetic acid as a catalyst, heating to 60 ℃, refluxing for 4 hours, crystallizing in an ice water bath, filtering to obtain precipitate, washing with ethanol for three times, and drying in vacuum to obtain a yellow powdery fluorescent compound 1 with the yield of 70%, wherein the fluorescent compound emits orange light under the irradiation of an ultraviolet lamp.
The seventh embodiment: dissolving 80mmol of hydrazine hydrate (85 mass percent) in 20ml of absolute ethyl alcohol, heating to 70 ℃, slowly dripping 40mmol of salicylaldehyde into a reactor under the condition of continuous stirring, refluxing for 3 hours, filtering while the salicylaldehyde is hot to obtain yellow powdery solid, washing with the absolute ethyl alcohol, putting the yellow powdery solid into an oven for drying to obtain salicylaldehyde hydrazone, dissolving the obtained salicylaldehyde hydrazone and 20mmol of 1, 4-benzaldehyde in 20ml of DMF, adding 0.8ml of acetic acid as a catalyst, heating to 70 ℃, refluxing for 6 hours, crystallizing in an ice water bath, filtering to obtain precipitate, washing with ethanol for three times, and drying in vacuum to obtain a yellow powdery fluorescent compound 1 with the yield of 72%, wherein the fluorescent compound emits orange light under the irradiation of an ultraviolet lamp.
Claims (8)
1. The preparation method of the salicylaldehyde-based fluorescent compound is characterized by comprising the following steps of:
(1) dissolving 40-80 mmol of hydrazine hydrate (mass fraction 85%) in 10-20 ml of absolute ethyl alcohol according to a molar volume ratio, heating to 60-70 ℃, slowly dropwise adding 40mmol of salicylaldehyde into a reaction container under the condition of continuous stirring, refluxing for 2-3 h, filtering while hot to obtain yellow powdery solid, washing with absolute ethyl alcohol, and drying to obtain salicylaldehyde hydrazone;
(2) dissolving salicylaldehyde hydrazone and 20-30 mmol 1, 4-benzaldehyde in 20-30 ml DMF according to molar volume ratio, adding 0.8-1.2 ml acetic acid as a catalyst, heating and refluxing for 4-6 h, crystallizing in an ice water bath, filtering to obtain a precipitate, washing with ethanol for three times, and drying to obtain a fluorescent compound 1 with the molecular formula of C22H18N4O2The concrete structure is as follows:
2. the preparation method according to claim 1, wherein in the step (1), the ratio of the hydrazine hydrate to the absolute ethyl alcohol is 40-80 mmol: 10 to 20 ml.
3. The preparation method according to claim 1, wherein in the step (1), the ratio of the hydrazine hydrate to the salicylaldehyde is 40-80 mmol: 40 mmol.
4. The preparation method according to claim 1, wherein in the step (1), the reaction temperature is 60-70 ℃ and the reflux time is 2-3 h.
5. The preparation method according to claim 1, wherein in the step (2), the ratio of the amount of 1, 4-benzenedialdehyde to DMF is 20-30 mmol: 20-30 ml.
6. The preparation method according to claim 1, wherein in the step (2), the ratio of the amount of the 1, 4-benzenedialdehyde to the amount of the acetic acid is 20-30 mmol: 0.8 to 1.2 ml.
7. The preparation method according to claim 1, wherein in the step (2), the reaction temperature is 40-50 ℃ and the reflux time is 4-6 h.
8. The method according to claim 1, wherein in the step (2), the residual ethanol is removed by vacuum drying after ethanol washing to obtain the fluorescent compound 1.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010489713.4A CN113754560A (en) | 2020-06-02 | 2020-06-02 | Preparation method of salicylaldehyde-based fluorescent compound |
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| CN202010489713.4A CN113754560A (en) | 2020-06-02 | 2020-06-02 | Preparation method of salicylaldehyde-based fluorescent compound |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114395247A (en) * | 2022-01-28 | 2022-04-26 | 福州大学 | Polyamide 6 fluorescent composite material and preparation method thereof |
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2020
- 2020-06-02 CN CN202010489713.4A patent/CN113754560A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114395247A (en) * | 2022-01-28 | 2022-04-26 | 福州大学 | Polyamide 6 fluorescent composite material and preparation method thereof |
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Application publication date: 20211207 |