CN107880276B - Light-operated fluorescent switch based on coordination polymer and preparation method and application thereof - Google Patents
Light-operated fluorescent switch based on coordination polymer and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a light-operated fluorescent switch based on a coordination polymer, a preparation method and application thereof, wherein the light-operated fluorescent switch is the coordination polymer 1- (zinc (1, 4-benzene diacetic acid) (4,4' -bi (4-pyridyl) -trans-stilbene)]nOr coordination polymer 2- (zinc (1, 4-benzenediacetic acid) (1,2,3, 4-tetrakis (4-phenyl-4' -pyridyl) cyclobutane)0.5]n.4, 4 '-bis (4-pyridyl) -trans-stilbene molecules and 1,2,3, 4-tetra (4-phenyl-4' -pyridyl) cyclobutane molecules in the coordination polymer can be freely switched under the radiation of different wavelengths of light, and the fluorescence emission intensity of the coordination polymer before and after conversion is obviously different. Therefore, the coordination polymer is a typical light-operated fluorescent switch and can be used as a rewritable optical recording material in the field of optical information storage.
Description
Technical Field
The invention relates to preparation and application of a novel fluorescent material, in particular to a light-operated fluorescent switch based on a coordination polymer and a preparation method and application thereof.
Background
The material capable of generating reversible reaction under external stimulation has chemical and physical properties which are often greatly different before and after the reaction, so that the material is widely applied to the aspects of advanced optical, electric, magnetic and mechanical devices and the like. The preparation of controllable optical switches is one of the most interesting areas, since by excitation with light, molecules can be reversibly switched between two stable states. The optical switch presents precise and controllable optical properties, so that the optical switch can be widely applied to the fields of light-operated fluorescent switches, rewritable optical information storage equipment, optical sensors, high-resolution microscopes and the like. Optical switches require a complete reversible transformation of a material from one stable state to another so as to ensure the "on" and "off" stable states of the material and correspondingly stable optical performance. To date, optical switches have been relatively few in type, mainly because most compounds do not possess photosensitive activity, and some photosensitive compounds have limited their application due to poor thermal stability. Therefore, the design and development of novel optical switch compounds have important scientific significance and wide application value.
Disclosure of Invention
In order to avoid the defects of the prior art, the invention aims to provide a light-operated fluorescent switch based on coordination polymer and a preparation method and application thereof, and the technical problem to be solved is to effectively select the synthesis method and synthesis route of the light-operated coordination polymer and the conversion condition of the reversible reaction. The coordination polymer has response to light with different wavelengths, and photosensitive molecules in the coordination polymer can be reversibly transformed under the irradiation of long-wave ultraviolet light and short-wave ultraviolet light.
The invention relates to a light-operated fluorescent switch based on a coordination polymer, which is the coordination polymer 1- (zinc (1, 4-benzene diacetic acid) (4,4' -bi (4-pyridyl) -trans-stilbene)]nOr coordination polymer 2- (zinc (1, 4-benzenediacetic acid) (1,2,3, 4-tetrakis (4-phenyl-4' -pyridyl) cyclobutane)0.5]n. n is the number of repeating units, is any positive integer, and represents that the structural unit repeatedly extends for a plurality of times.
The invention relates to a preparation method of a light-operated fluorescent switch based on coordination polymers, which comprises the following steps:
step 1: preparation of organic ligands
4.32g (10mmol) of 4,4' -diiodo-trans-stilbene, 2.95g (24mmol) of 4-pyridineboronic acid, 0.14g (2 mol) of tetrakis (triphenylphosphine) palladium, 8.15g (25mmol) of cesium carbonate and N, N ' -dimethylformamide (40mL) were charged into a 100mL Schlenk flask, the air in the flask was replaced with high-purity nitrogen gas, and the reaction was stirred at 85-95 ℃ for 12 hours to obtain an organic ligand, 4' -bis (4-pyridyl) -trans-stilbene;
step 2: synthesis of coordination Polymer 1
Adding 1.67g (5mmol) of 4,4' -bis (4-pyridyl) -trans-stilbene, 0.96g (5mmol) of 1, 4-benzenediacetic acid, 1.49g (5mmol) of zinc nitrate hexahydrate and deionized water (90mL) into a 150mL reaction kettle, reacting for 72 hours at the constant temperature of 175 ℃, and then cooling to 5 ℃ per hour to room temperature to obtain a light yellow coordination polymer 1 crystal;
and step 3: synthesis of coordination Polymer 2
Coordination polymer 1(1.18g, 2mmol) was placed in a petri dish with a diameter of 8cm and then placed under an LED lamp (20W) with an emission wavelength of 365nm for 2 hours under illumination at a distance of 2cm, and then completely converted into crystals of coordination polymer 2.
The light-operated fluorescent switch is in an on state to an off state, namely a process of converting coordination polymer 1 into coordination polymer 2, specifically, a single crystal of coordination polymer 1 is placed under an LED lamp (20W) with an emission wavelength of 365nm at a distance of 2cm for illumination for 2 hours, and coordination polymer 1 can be completely converted into coordination polymer 2.
The reverse reaction process of the light-operated fluorescent switch from 'off' to 'on' state, namely the process of converting coordination polymer 2 into coordination polymer 1, specifically, the single crystal of coordination polymer 2 is placed under a low-pressure mercury lamp (50W) with emission wavelength of 254nm for 2cm to illuminate for 2 hours, and coordination polymer 2 is completely converted into coordination polymer 1.
The reversible conversion process of 4,4 '-bis (4-pyridyl) -trans-stilbene and 1,2,3, 4-tetra (4-phenyl-4' -pyridyl) cyclobutane in the photosensitive coordination polymer material under the two states of 'on' and 'off' of the light-operated fluorescent switch is as follows:
the invention relates to an application of a light-operated fluorescent switch based on coordination polymer, which is an application of the light-operated fluorescent switch as a fluorescent switch material in the field of optical information storage.
The invention relates to an application of a light-operated fluorescent switch based on coordination polymers, which can be reversibly transformed under the irradiation of long-wave ultraviolet light and short-wave ultraviolet light, and comprises the following specific processes:
placing the single crystal of the coordination polymer 1 under an LED lamp (20W) with the emission wavelength of 365nm at a distance of 2cm for illumination for 2 hours, wherein the coordination polymer 1 can be completely converted into a coordination polymer 2; by exposing the single crystal of coordination polymer 2 to light for 2 hours at a distance of 2cm under a low-pressure mercury lamp (50W) having an emission wavelength of 254nm, coordination polymer 2 was completely converted into coordination polymer 1.
The coordination polymer 1 of the invention can emit green fluorescence (lambda) under the excitation of light with the wavelength of 420nmmax529nm) and coordination polymer 2 has a 78.1% reduction in fluorescence intensity relative to coordination polymer 1 under the same excitation conditions.
4,4 '-bis (4-pyridyl) -trans-stilbene molecules and 1,2,3, 4-tetra (4-phenyl-4' -pyridyl) cyclobutane molecules in the coordination polymer can be freely switched under the radiation of different wavelengths of light, and the fluorescence emission intensity of the coordination polymer before and after conversion is obviously different. Therefore, the coordination polymer is a typical light-operated fluorescent switch and can be used as a rewritable optical recording material in the field of optical information storage.
The preparation method has the advantages of simple process, mild reaction conditions and high yield.
Drawings
FIG. 1 shows [ Zn (1, 4-benzenediacetic acid) (4,4' -bis (4-pyridyl) -trans-stilbene ]]nCrystal structure of (2).
FIG. 2 shows [ Zn (1, 4-benzenediacetic acid) (4,4' -bis (4-pyridyl) -trans-stilbene ]]nNuclear magnetic resonance hydrogen spectrum of (a).
FIG. 3 shows [ Zinc (1, 4-Benzenediacetic acid) (1,2,3, 4-tetrakis (4-phenyl-4' -pyridyl) cyclobutane)0.5]nCrystal structure of (2).
FIG. 4 shows [ Zinc (1, 4-Benzenediacetic acid) (1,2,3, 4-tetrakis (4-phenyl-4' -pyridyl) cyclobutane)0.5]nNuclear magnetic resonance hydrogen spectrum of (a).
FIG. 5 shows the reverse reaction to form [ Zn (1, 4-benzenediacetic acid) (4,4' -bis (4-pyridyl) -trans-stilbene ]]nNuclear magnetic resonance hydrogen spectrum of (a).
FIG. 6 shows [ Zn (1, 4-benzenediacetic acid) (4,4' -bis (4-pyridyl) -trans-stilbene ]]nAnd [ zinc (1, 4-benzenediacetic acid) (1,2,3, 4-tetrakis (4-phenyl-4' -pyridyl) cyclobutane)0.5]nFluorescence emission spectrum of [ zinc (1, 4-benzenediacetic acid) (4,4' -bis (4-pyridyl) -trans-stilbene ]]nFluorescence photograph of single crystal.
FIG. 7 shows [ Zinc (1, 4-Benzenediacetic acid) (1,2,3, 4-tetrakis (4-phenyl-4' -pyridyl) cyclobutane)0.5]nLaser scanning confocal micro-fluorescence photographs of single crystals for optical information storage.
Detailed Description
Non-limiting examples are set forth below:
4,4 '-diiodo-trans-stilbene, 1, 4-benzenediacetic acid, 4-pyridineboronic acid, cesium carbonate, tetrakis (triphenylphosphine) palladium were all purchased from Shanghai Bailingwei chemical technology Co., Ltd, and sodium hydroxide, anhydrous magnesium sulfate, dichloromethane, and N, N' -dimethylformamide were purchased from national pharmaceutical group Chemicals Co., Ltd.
1. Preparation of organic ligands
4.32g (10mmol) of 4,4 '-diiodo-trans-stilbene, 2.95g (24mmol) of 4-pyridineboronic acid, 0.14g (2 mol%) of tetrakis (triphenylphosphine) palladium, 8.15g (25mmol) of cesium carbonate and N, N' -dimethylformamide (40mL) were charged into a 100mL Schlenk flask, the air in the flask was replaced with high-purity nitrogen gas, and then the mixture was stirred at a temperature of about 90 ℃ to complete the reaction for about 12 hours.
After the reaction is stopped, adding excessive water into the reaction bottle, extracting with 100mL of dichloromethane for three times respectively, and combining organic phases; with 2 mol. L-1The organic phase was washed three times with sodium hydroxide solution, dried over anhydrous magnesium sulfate and finally rotary evaporated to remove dichloromethane to give 4,4' -bis (4-pyridyl) -trans-stilbene as a beige solid in a mass of 2.74g in 82% yield.
The product 4,4' -bis (4-pyridyl) -trans-stilbene is subjected to element analysis and nuclear magnetic resonance hydrogen spectrum characterization. The results are as follows:
elemental analysis (C)24H18N2) Theoretical value (%): C, 86.20; h, 5.43; n, 8.38; the experimental values (%): C, 86.38; h, 5.31; and N, 8.53.
1H NMR(400MHz,DMSO-d6,298K,TMS):δ＝8.63(d,J＝5.2Hz,4H),7.87(d,J＝8.4Hz, 4H),7.77(m,8H),7.45(s,2H)。
2. Synthesis of target product 1
4,4' -bis (4-pyridyl) -trans-stilbene 1.67g (5mmol), 1, 4-benzenediacetic acid 0.96g (5mmol), zinc nitrate hexahydrate 1.49g (5mmol) and deionized water (90mL) were added to a 150mL reaction vessel, reacted at 175 ℃ for 72 hours at constant temperature, and then cooled to room temperature by 5 ℃ per hour to give 2.54g of crystals of pale yellow coordination polymer 1 in 86% yield. The crystallographic parameters are as follows:
crystallographic parameters of coordination polymer 1: c34H26N2O4Zn,Mr＝591.96,triclinic,space group
α＝97.63(3)°,β＝104.80(3)°,γ＝98.88(3)°,
Z＝2,Dc＝1.417g cm-3,μ＝0.928mm-1,25374reflectionsmeasured,6316unique reflections(Rint＝0.0259),5448 observed reflections(I>2σ(I)),612parameters,R1＝0.0368,wR2＝0.0991,S＝1.031。
The structure of the X-ray single crystal of coordination polymer 1 is shown in FIG. 1.
1H NMR(400MHz,DMSO-d6298K, TMS): δ 8.64(d, J ═ 6.0Hz,4H),7.87(d, J ═ 8.4Hz,4H), 7.78(m,8H),7.46(s,2H),7.18(s,4H),3.52(s, 4H). See fig. 2.
Infrared of v (KBr)/cm-11615s,1591s,1559s,1430s,1381s,1235m,1182w,1109m,1041m,965s, 850w,783s,696s,643m,498m。
3. Production of target product 2 from target product 1
The target product 1(1.18g, 2mmol) was placed in a petri dish with a diameter of 8cm and then placed under an LED lamp (20W) with an emission wavelength of 365nm for 2 hours under illumination at a distance of 2cm, and then the crystal was completely converted into 1.18g of the target product 2 with a yield of 100%. The crystallographic parameters are as follows:
crystallographic parameters of coordination polymer 2: c34H26N2O4Zn,Mr＝591.96,triclinic,space group
α＝94.76(3)°,β＝106.97(3)°,γ＝98.35(3)°,
Z＝2,Dc＝1.430g cm-3,μ＝0.936mm-1,23515reflectionsmeasured,6311unique reflections(Rint＝0.0352),4630observed reflections(I>2σ(I)),612parameters,R1＝0.0487,wR2＝0.1215,S＝1.038.
The structure of the X-ray single crystal of coordination polymer 2 is shown in FIG. 3.
1H NMR(400MHz,DMSO-d6298K, TMS): δ 8.55(d, J ═ 6.0Hz,4H),7.63(m,8H),7.43(d, J ═ 8.4Hz,4H),7.18(s,4H),4.72(s,2H),3.52(s, 4H). See fig. 4.
Infrared of v (KBr)/cm-11616s,1591s,1556s,1430s,1379s,1241m,1184w,1110m,1043m,965s, 851w,783s,717s,645m,498m。
4. Can be reversibly changed into a target product 1 from a target product 2
The desired product 2(0.59g, 1mmol) was placed in a petri dish having a diameter of 8cm and then placed under a low-pressure mercury lamp (50W) having an emission wavelength of 254nm under light for 2 hours at a distance of 2cm, to thereby completely convert the desired product 2 into crystals of 0.59g at a yield of 100%.
1H NMR(400MHz,DMSO-d6298K, TMS): δ 8.64(d, J ═ 6.0Hz,4H),7.87(d, J ═ 8.4Hz,4H), 7.77(m,8H),7.45(s,2H),7.18(s,4H),3.52(s, 4H). See fig. 5.
Infrared of v (KBr)/cm-11615s,1590s,1556s,1430s,1381s,1235m,1183w,1109m,1041m,965s, 850w,783s,696s,644m,498m。
5. Fluorescent properties of coordination polymers
The target product 1 can emit green fluorescence (lambda) under the excitation of light with the wavelength of 420nmmax529nm) and the fluorescence intensity of target product 2 is reduced by 78.1% relative to target product 1 under the same conditions. See fig. 6.
Therefore, the distinct fluorescent properties of target products 1 and 2 and the reversible transformation between them indicate that they are typical optically controlled fluorescent switches and can be applied as rewritable optical recording materials in the field of optical information storage.
A photomask with transparent dots is covered on one single crystal of the target product 2, and a transparent origin on the photomask forms a pattern of the English letter SCSC. After 2 hours of irradiation with 254nm light, the photomask was removed and the SCSC pattern was found to be clearly recorded on the single crystal of the target product 2 using laser scanning confocal microscopy. See fig. 7.
Claims (5)
1. A coordination polymer-based optically controlled fluorescent switch, comprising: the light-operated fluorescent switch is coordination polymer 1- (zinc (1, 4-benzene diacetic acid) (4,4' -bi (4-pyridyl) -trans-stilbene)]nOr coordination polymer 2- (zinc (1, 4-benzenediacetic acid) (1,2,3, 4-tetrakis (4-phenyl-4' -pyridyl) cyclobutane)0.5]nAnd n is the number of repeating units, is any positive integer and represents that the structural unit repeatedly extends for multiple times.
2. A method of making a coordination polymer-based optically controlled fluorescent switch according to claim 1, comprising the steps of:
step 1: preparation of organic ligands
4,4' -diiodo-trans-stilbene 4.32g, 4-pyridineboronic acid 2.95g, tetrakis (triphenylphosphine) palladium 0.14g, cesium carbonate 8.15g and N, N ' -dimethylformamide were added to a 100mL Schlenk flask, the air in the flask was replaced with high-purity nitrogen, and the reaction was stirred at 85 to 95 ℃ for 12 hours to obtain an organic ligand, 4' -bis (4-pyridyl) -trans-stilbene;
step 2: synthesis of coordination Polymer 1
Adding 1.67g of 4,4' -bis (4-pyridyl) -trans-stilbene, 0.96g of 1, 4-benzenediacetic acid, 1.49g of zinc nitrate hexahydrate and deionized water into a 150mL reaction kettle, reacting at the constant temperature of 175 ℃ for 72 hours, and then cooling to 5 ℃ per hour to room temperature to obtain a crystal of a light yellow coordination polymer 1;
and step 3: synthesis of coordination Polymer 2
11.18 g of coordination polymer was placed in a 8 cm-diameter petri dish and then placed under an LED lamp having an emission wavelength of 365nm for 2 hours under illumination at a distance of 2cm, thereby completely converting into crystals of coordination polymer 2.
3. Use of the coordination polymer-based photoswitching switch of claim 1, wherein: the fluorescent material is applied as a fluorescent switch material in the field of optical information storage.
4. Use of a coordination polymer-based optically controlled fluorescent switch according to claim 1, wherein: the light-operated fluorescent switch can realize reversible conversion under the irradiation of long-wave ultraviolet light and short-wave ultraviolet light.
5. Use according to claim 4, characterized in that:
placing the single crystal of the coordination polymer 1 under an LED lamp with the emission wavelength of 365nm at a distance of 2cm for illumination for 2 hours, and completely converting the coordination polymer 1 into a coordination polymer 2; the single crystal of coordination polymer 2 was placed under a low-pressure mercury lamp having an emission wavelength of 254nm and irradiated with light for 2 hours at a distance of 2cm, and coordination polymer 2 was completely converted into coordination polymer 1.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250264A (en) * | 2008-03-26 | 2008-08-27 | 天津师范大学 | High nuclear zinc coordination polymer as well as preparation method and uses thereof |
| CN103204883A (en) * | 2013-04-19 | 2013-07-17 | 南开大学 | Cobalt coordination polymer with reversible monocrystal-monocrystal transformation behavior |
| CN104804024A (en) * | 2015-04-27 | 2015-07-29 | 淮阴师范学院 | Highly connected coordination polymer and preparation method thereof |
| CN106380606A (en) * | 2016-09-12 | 2017-02-08 | 桂林理工大学 | Zinc isophthalate coordination polymer and preparation method thereof |
| CN106478960A (en) * | 2016-10-01 | 2017-03-08 | 桂林理工大学 | The zinc complex constructed with trimesic acid and double (4 pyridine radicals) amine and preparation method |
| CN107325030A (en) * | 2016-10-27 | 2017-11-07 | 东北林业大学 | The new trans-stilbene class antitumor agent of one class |
-
2017
- 2017-12-01 CN CN201711248393.8A patent/CN107880276B/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250264A (en) * | 2008-03-26 | 2008-08-27 | 天津师范大学 | High nuclear zinc coordination polymer as well as preparation method and uses thereof |
| CN103204883A (en) * | 2013-04-19 | 2013-07-17 | 南开大学 | Cobalt coordination polymer with reversible monocrystal-monocrystal transformation behavior |
| CN104804024A (en) * | 2015-04-27 | 2015-07-29 | 淮阴师范学院 | Highly connected coordination polymer and preparation method thereof |
| CN106380606A (en) * | 2016-09-12 | 2017-02-08 | 桂林理工大学 | Zinc isophthalate coordination polymer and preparation method thereof |
| CN106478960A (en) * | 2016-10-01 | 2017-03-08 | 桂林理工大学 | The zinc complex constructed with trimesic acid and double (4 pyridine radicals) amine and preparation method |
| CN107325030A (en) * | 2016-10-27 | 2017-11-07 | 东北林业大学 | The new trans-stilbene class antitumor agent of one class |
Non-Patent Citations (2)
| Title |
|---|
| A highly selective ratiometric fluorescent chemosensor for Hg2+ based;Shuhong Jing 等;《Dyes and Pigments》;20041231;第107卷;38-44 * |
| A novel diarylethene-based;Xiaodong Zhang 等;《Journal of Photochemistry and Photobiology A:》;20161231;第330卷;22-29 * |
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