CN113045597A - Visible light driven boron-doped thick photochromic material and preparation and application thereof - Google Patents
Visible light driven boron-doped thick photochromic material and preparation and application thereof Download PDFInfo
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Abstract
The invention belongs to the field of photoelectric materials, and particularly discloses a visible light driven photochromic material. The material of the invention has great application prospect in the technical fields of optical information storage, logic gates, anti-counterfeiting, lossless data reading and the like.
Description
Technical Field
The invention relates to the field of organic photochromic materials, in particular to a visible light driven boron doped thick photochromic material.
Background
The potential applications of visible light driven photochromic switch molecules in the fields of photoswitches, bioimaging, and photopharmacology have attracted considerable attention, primarily because of the less destructive and hazardous nature of visible light to optical devices and biological cells. At present, the design of visible light driven diarylethene molecules generally extends the conjugated system of aryl units, reduces the HOMO-LUMO energy gap of ring-opened isomers, and enables the ring-opened isomers to have absorption in the visible region. Lehn et al, 1997, have first synthesized a visible light-driven diarylethene compound by introducing two thiophene rings at the 5-and 5' -positions of the thiophene ring, respectively, to make the absorption of the open/closed ring isomers reach the visible region. It was found that an increase in the aryl pi system leads to a decrease in the open/ring quantum yield (. PHI.) (o–cAnd phic–oLess than 0.01), thereby limiting the development of visible light driven diarylethene photochromic functional materials.
Heteroatom doping can regulate and control the electronic structure and the physicochemical property of a conjugated pi system. The boron hetero-condensed ring system has typical Lewis acidity and electron acceptor capacity, and can provide electron delocalized channel for pi electrons of a conjugated system. However, boron atoms themselves are extremely electrophilic, and particularly exhibit high sensitivity to air, water and the like, and the development of the boron hetero fused ring system is limited to a certain extent.
Disclosure of Invention
The first purpose of the invention is to provide a visible light driven photochromic material with a brand new structure.
The second purpose of the invention is to provide a preparation method of the visible light driven boron doped thick photochromic material with a brand new structure.
The third purpose of the invention is to provide the application of the visible light driven boron doped thick photochromic material.
The fourth purpose of the invention is to provide a visible light driven boron doped thick photochromic device.
A visible light driven boron doped thick photochromic material has a structural general formula of formula 1:
ar is1、Ar2Independently is heterocyclic aryl or heterocyclic aryl with substituent, and the substituent is halogen and C1～C6Alkyl radical, C1～C6At least one of alkoxy, phenyl and substituted phenyl;
said X1、X2O, S or N independently;
said R1Is an aromatic group, a substituted aromatic group;
ar is3Is an aromatic group or a substituted aromatic group.
The invention provides a compound with a brand new structure, and the structure based on the compound is found to enable the compound to have photochromic characteristics under the drive of visible light, and moreover, the compound also has excellent quantum yield and fluorescence change, so that the compound has a larger application prospect in the field of nondestructive identification.
Preferably, Ar is1、Ar2The heterocyclic aryl group is preferably a five-membered heterocyclic aryl group or a six-membered heterocyclic aryl group; or a five-membered heterocyclic ring or a six-membered heterocyclic ring having a substituent. The heteroatom in said heterocyclic aryl group is for example O, S or a N heteroatom; the number of hetero atoms is preferably 1 to 3. Further preferably, Ar is1、Ar2Is a thiophene ring or a thiophene ring with the substituent.
In the present invention, Ar is3Is five-membered heterocyclic aryl, phenyl, six-membered heterocyclic aryl, or condensed ring aryl formed by the condensation of two or more aromatic rings in the five-membered heterocyclic aryl, phenyl and six-membered heterocyclic aryl;
the aromatic ring of the five-membered heterocyclic aryl, the phenyl, the six-membered heterocyclic aryl and the condensed ring aryl is allowed to have a substituent;
said substituent is preferably C1～C6Alkyl of (C)1～C6Alkoxy, halogen, nitro, phenyl, benzyl.
Preferably, Ar is3Is phenyl or substituted phenyl.
In the present invention, X is1、X2Independently is O, S or an N heteroatom when X1Or X2When N is N, N also has R substituent; said R substituent being, for example, C1～C6Alkyl group of (1). Further preferably, X is1、X2Independently is O or S; further preferred is X1Is S, X2Is O.
In the present invention, R1The aromatic group is preferably a five-membered heterocyclic aryl group, a phenyl group, a six-membered heterocyclic aryl group, or a condensed ring aryl group formed by condensing two or more aromatic rings in the five-membered heterocyclic aryl group, the phenyl group and the six-membered heterocyclic aryl group; the aromatic ring of the five-membered heterocyclic aryl, the phenyl, the six-membered heterocyclic aryl and the condensed ring aryl is allowed to have a substituent; said substituent is preferably C1～C6Alkyl of (C)1～C6Alkoxy, halogen, nitro, phenyl, benzyl.
Further preferably, R is1Is phenyl or substituted phenyl.
The substituted phenyl group of the present invention has 1 to 5 substituents selected from C1～C3Alkyl of (C)1～C3Alkoxy of (2) and phenyl as a substituent in the halogen.
Preferably, the visible light driven boron doped photochromic material has the following structural formula:
said X1、X2O, S or NR alone;
said R1Independently is phenyl or substituted phenyl.
Further preferably, the visible light driven boron hybrid thick photochromic material preferably has the following structural formula:
in the formula 1-A, the R2、R3、R4、R5Is alone H, C1～C6Alkyl of (C)1～C6Alkoxy or halogen of (a); said X1、X2O, NR or S independently; said R1Independently phenyl or alkyl substituted phenyl.
Preferably, in formula 1-A, R is2、R3、R4、R5The same substituents are preferred.
Further preferably, R is2、R3、R4、R5Is methyl.
The invention also provides a preparation method of the visible light driven boron hybrid thick photochromic material, which comprises the steps of carrying out coupling reaction on a compound shown in a formula 2 and a compound shown in a formula 3 to prepare a compound shown in a formula 4; then the compound of formula 4 and boron trihalide are subjected to ring closure reaction, and then R is used1MgX quenching reaction to obtain the visible light driven photochromic material;
y is halogen; said R6Is C1～C6Alkyl groups of (a); said R7、R8Is H, C1～C6Or a cyclic ether structure (the selection range of other substituents in the formulas 2 to 3 is the same as that in the formula 1).
According to the technical scheme, the visible light driven photochromic material can be obtained with high yield and high purity based on the coupling and ring closing and format reagent quenching substitution preparation process. According to the technical scheme, a brand new compound is prepared, and the brand new compound can show good photochromic reaction characteristics without being excited by high-energy ultraviolet light.
In the invention, the coupling reaction is carried out under the action of alkali and a catalyst;
the alkali is at least one of hydroxide, carbonate, bicarbonate and phosphate of alkali metal.
Preferably, the amount of the base used is not less than the theoretical reaction amount, preferably 6 to 10 times the theoretical reaction amount.
Preferably, the catalyst is a palladium catalyst, preferably tetrakis (triphenylphosphine) palladium; the amount of the catalyst is 5-20 mol% of the compound of formula 2.
The solvent for the coupling reaction is a solvent capable of dissolving the raw materials of formulae 2 and 3, and is at least one of toluene, ethanol, water, and the like.
The temperature during the coupling reaction may be reflux.
In the present invention, the coupling product (compound of formula 4) and boron trihalide are subjected to ring closure, and R is used1Quenching MgX to obtain the visible light driven photochromic material;
in the present invention, the boron trihalide is preferably boron tribromide, and more preferably 1 to 1.5 times the theoretical reaction amount.
The solvent for the boron ring-closing reaction and quenching process is preferably a solvent capable of dissolving the reactant, for example, a hydrophobic solvent, and more preferably anhydrous toluene.
The temperature of the ring closing reaction process is preferably 0 ℃ and then refluxing. Preferably, the temperature in the feeding process is 0-5 ℃, and the reflux is carried out after the feeding is finished.
The time of the ring-closing reaction is, for example, 6 to 24 hours.
Further preferably, R is1MgX is 2,4, 6-trimethylbenzene magnesium bromide; preferably, R is1MgX is not less than the theoretical reaction amount, and more preferably 2 to 2.5 times the theoretical reaction amount.
The temperature of the quenching reaction is preferably 0-5 ℃.
The invention also provides application of the visible light driven boron hybrid thick photochromic material, and the application of the visible light driven boron hybrid thick photochromic material is used for a reversible photochromic material under the drive of visible light.
Preferably, the use is for materials for at least one of anti-counterfeiting, information storage, logic gates, and non-destructive data readout.
The invention also provides a visible light driven photochromic device which comprises the visible light driven photochromic material.
Advantageous effects
1. The invention provides a compound with a brand-new structure. It was found that, based on the structure of the said novel compound, it was possible to achieve surprisingly visible light-driven photochromism, but also excellent quantum yields.
The research finds that the compound shown in the formula 1 can be reversibly interconverted under the irradiation of UV and visible light, the fluorescence intensity of the compound is slowly reduced along with the photochromic reaction process, because the ultraviolet absorption spectrum and the fluorescence emission spectrum of the closed-ring compound are overlapped, an energy transfer (FRET) process exists to cause fluorescence quenching, and the fluorescence quantum yield of the pure product of the separated open-ring compound is phiF2.14%. The quantum yield of photocyclization and photoring reduction is respectively 0.47 and 0.26, the conversion rate of photocyclization is 71 percent,
2. the visible light driven photochromic material can be obtained through simple coupling and boron ring closing treatment;
3. the invention develops and processes the brand new compound and has wide application prospect in the fields of anti-counterfeiting, information storage, logic gates, nondestructive data reading and the like.
Drawings
FIG. 1 shows the NMR spectrum of a compound of formula B obtained in example 1.
FIG. 2 is a NMR carbon spectrum of formula B obtained in example 1.
FIG. 3 is a NMR spectrum of formula C obtained in example 1.
FIG. 4 is a NMR carbon spectrum of the compound of formula C obtained in example 1.
FIG. 5 shows the NMR spectrum of formula D obtained in example 1.
FIG. 6 is a carbon nuclear magnetic resonance spectrum of the compound of formula D obtained in example 1.
FIG. 7 shows the UV absorption spectrum of (A) under the illumination of formula D prepared in example 1, with the color of the solution before and after the illumination of formula D being plotted. (B) A reversible cyclic photochromic of formula D.
FIG. 8 is a fluorescence spectrum of the compound of formula D obtained in example 1 with light (excitation wavelength 376 nm).
FIG. 9 is a comparison of the NMR spectra of the open-closed cyclic compounds of formula D obtained in example 1.
Detailed Description
Example 1
To a dry 100mL single-neck flask were added compound a (200mg, 0.4mmol) and anhydrous dichloromethane (50mL), and after sufficient dissolution, it was cooled to 0 ℃. N-bromosuccinimide (79.5mg, 0.4mmol) was added portionwise under the exclusion of light. The reaction was carried out for 4h at room temperature in the dark and the reaction progress was monitored by spotting. After the reaction was completed, 2mL of water was added to quench the reaction. Followed by extraction with 50mL of saturated brine and 50mL of dichloromethane. Anhydrous Na for organic phase2SO4Drying, filtering and removing the solvent. The residue was flash-purified with a silica gel chromatography column (petroleum ether) to give 227mg of yellow compound B in 98% yield.
The structure of the compound of formula B is confirmed by means of hydrogen and carbon nuclear magnetic resonance spectroscopy.
1H NMR(400MHz,CDCl3):δ7.71(d,J＝7.6Hz,2H),7.34(t,J＝7.4Hz,2H),7.18(t,J＝7.3Hz,2H),7.05(d,J＝7.5Hz,2H),6.82(s,1H),6.45(s,1H),5.27(s,1H),2.46(s,3H),1.99(s,3H),1.90(s,3H),1.71(s,3H).
13C NMR(100MHz,CDCl3):δ149.2,147.3,144.1,142.2,136.6,134.8,134.5,134.3,133.5,131.5,131.2,127.9,127.5,125.2,124.1,123.9,123.2,120.2,111.8,68.7,15.3,15.0,14.4,13.9.
A100 mL two-necked round-bottomed flask was charged with Compound B (200mg, 0.3mmol), 2-methoxyphenylboronic acid (69.1mg, 0.4mmol), and potassium carbonate (386.9mg, 2.8mmol), and after replacing nitrogen three times, toluene (35mL), ethanol (10mL), and water (2mL) were added. Under a nitrogen protection atmosphere, air was blown for 30min, and then tetrakis (triphenylphosphine) palladium (23.0mg, 0.02mmol) was added. The reaction was heated to reflux overnight and the progress of the reaction was monitored by spotting plates. After the reaction was completed, the mixture was extracted with 50mL of saturated brine and 100mL of ethyl acetate. Anhydrous Na for organic phase2SO4Drying, filtering and removing the solvent. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to give 163mg of the yellow compound of formula C in 78% yield.
The structure of the compound of formula C is confirmed by means of hydrogen nuclear magnetic resonance spectroscopy and carbon spectroscopy.
1H NMR(400MHz,CDCl3):δ7.73(d,J＝7.6Hz,2H),7.49(d,J＝7.8Hz,1H),7.34(t,J＝7.4Hz,2H),7.19-7.09(m,5H),6.86-6.91(m,4H),5.27(s,1H),3.88(s,3H),2.48(s,3H),2.00(s,3H),1.94(s,3H),1.72(s,3H).
13C NMR(100MHz,CDCl3):δ155.1,149.8,147.8,145.1,142.2,140.5,136.1,134.5,134.4,134.2,134.1,131.9,127.7,127.6,127.4,125.8,124.2,123.5,120.8,120.0,119.1,111.5,68.4,55.5,15.3,15.1,14.5,13.9.
To a dry 50mL two-necked round bottom flask, under a nitrogen blanket, was added compound C (100mg, 0.2mmol) and dry toluene (15 mL). After sufficient dissolution, it was cooled to 0 ℃. In the above system, boron tribromide solution (1M, 0.18mL, 0.2mmol) was slowly added dropwise. After the reaction is carried out for 0.5h, the mixture is slowly heated and refluxed and reacted overnight (7-12 h). The reaction was cooled to 0 ℃ and a solution of 2,4, 6-trimethylbenzenemagnesium bromide (0.5M,1mL, 0.5mmol) was slowly added dropwise. The reaction was heated slowly to reflux for 2h and the reaction was monitored by spotting plates. After the reaction was completed, 50mL of saturated brine and 50mL of dioxane were usedExtracting with chloromethane, and extracting organic phase with anhydrous Na2SO4Drying, filtering and removing the solvent. The residue was purified by flash chromatography on silica gel (petroleum ether/dichloromethane ═ 10:1) to give 53mg of the pale yellow compound of formula D in 45% yield.
The structure of the compound of formula D is confirmed by means of hydrogen and carbon nuclear magnetic resonance spectroscopy.
1H NMR(400MHz,CDCl3)δ7.91(d,J＝7.8Hz,1H),7.42-7.28(m,3H),7.18-7.17(m,4H),7.06-7.02(m,2H),6.96-6.90(m,3H),6.22(s,2H),4.85(s,1H),2.49(s,3H),2.25(s,3H),1.91(s,3H),1.87(s,3H),1.63(s,3H),1.32(s,6H).
13C NMR(100MHz,CDCl3)δ154.6,151.9,150.3,148.8,146.5,143.5,142.7,138.8,136.5,136.4,134.7,134.4,133.7,132.3,131.4,131.3,128.4,127.9,127.1,126.8,126.7,125.4,124.1,123.4,123.3,122.7,122.5,120.3,119.9,76.7,69.2,22.4,21.7,21.2,15.4,14.9,14.4,13.8.
Example 2:
at room temperature, we are right at 5X 10-5A tetrahydrofuran solution of the compound D in mol/L was subjected to ultraviolet absorption spectroscopy, and the results are shown in FIG. 7 (A). Compound D at 382nm (ε ═ 2.64X 104L mol-1cm-1) A strong absorption peak appears, the absorption end extends to about 445nm and can be excited by visible light. After being irradiated by visible light of 400nm, the compound D has ring closure reaction and has the ring closure reaction at 487nm (epsilon is 5.66X 10)3Lmol-1cm-1) New absorption bands appear. With the light irradiation time, a light steady state was reached after 45 s. This process is also accompanied by a color change of the compound, the solution changing from colorless to yellow. But in the visible (lambda)>450nm) light, the yellow solution returns to the original colorless solution. As shown in FIG. 7(B), the tetrahydrofuran solution of Compound D was repeatedly circulated ten times or more by alternate short-wave and long-wave excitation.
Example 4:
fluorescence properties of compound D in tetrahydrofuran solution. As a result, as shown in FIG. 8, a significant fluorescence emission peak appeared at 446nm, and as the light irradiation was prolonged, the fluorescence intensity was gradually reduced at that point, and the fluorescence intensity was gradually reduced at that pointAfter 45s a light steady state is reached. This is probably due to the overlap of the ultraviolet absorption spectrum and the fluorescence emission spectrum of the closed ring isomer D, and the presence of energy transfer (FRET) processes, resulting in fluorescence quenching. The separated pure product of the ring-opening isomer D is tested to have the fluorescence quantum yield phi of the tetrahydrofuran solutionF2.14% (with 0.5M quinoline sulfate as reference).
Example 5:
the photochromic conversion of compound D can be calculated by the integrated area ratio of the hydrogen spectrum of nuclear magnetic resonance. As shown in FIG. 9, the closed ring isomer of the compound was dissolved in deuterated chloroform solution, and its proton H was observedaThe chemical shift was 4.85 ppm. In the photostable state, the proton HaThe chemical shift was 4.09 ppm. The integral area ratio of the two gives 71% conversion of the closed-ring isomer of the compound.
Claims (10)
1. A visible light driven boron doped thick photochromic material is characterized by having a structural general formula of a formula 1:
ar is1、Ar2Independently is heterocyclic aryl or heterocyclic aryl with substituent, and the substituent is halogen and C1～C6Alkyl radical, C1～C6At least one of alkoxy, phenyl and substituted phenyl;
said X1、X2O, S or N independently;
said R1Is an aromatic group, a substituted aromatic group;
ar is3Is an aromatic group or a substituted aromatic group.
2. The visible-light-driven boron hybrid photochromic material of claim 1 wherein Ar is3Is five-membered heterocyclic aryl, phenyl, six-membered heterocyclic aryl, or is composed of five-membered heterocyclic aryl, phenyl, six-membered heterocyclic arylA condensed ring aryl group formed by condensing two or more aromatic rings in the ring aryl group;
the aromatic ring of the five-membered heterocyclic aryl, the phenyl, the six-membered heterocyclic aryl and the condensed ring aryl is allowed to have a substituent;
said substituent is preferably C1～C6Alkyl of (C)1～C6Alkoxy, halogen, nitro, phenyl, benzyl.
3. The visible light driven, boron heterofused photochromic material of claim 1 having the formula:
said X1、X2O, S or NR alone;
said R1Independently is phenyl or substituted phenyl;
preferably, the visible light driven boron hetero-thick photochromic material has a structure of formula 1-A:
in the formula 1-A, the R2、R3、R4、R5Is alone H, C1～C6Alkyl of (C)1～C6Alkoxy or halogen of (a); said X1、X2O, N or S, independently; said R1Independently is phenyl or alkyl substituted phenyl;
preferably, in formula 1-A, R is2、R3、R4、R5Preferably the same substituent;
further preferably, R is2、R3、R4、R5Is methyl.
4. A kind ofThe preparation method of the visible light driven boron hybrid thick photochromic material of any one of claims 1 to 3, wherein the compound of formula 2 and the compound of formula 3 are subjected to coupling reaction to prepare a compound of formula 4; then the compound of formula 4 and boron trihalide are subjected to ring closure reaction, and then R is used1MgX quenching reaction to obtain the visible light driven photochromic material;
said R6Is C1～C6Alkyl groups of (a); said R7、R8Is H, C1～C6Or a ring-synthesized cyclic ether structure;
and Y is halogen.
5. The method of preparing the visible light driven bora-hybrid photochromic material of claim 4 wherein the coupling reaction is carried out in the presence of a base and a catalyst;
the alkali is at least one of hydroxide, carbonate, bicarbonate and phosphate of alkali metal;
the catalyst is a palladium catalyst, preferably tetrakis (triphenylphosphine) palladium; the amount of the catalyst is 5-20 mol% of the compound of formula 2.
6. The method for producing a visible light-driven boron heterodense photochromic material as claimed in claim 4, wherein the boron trihalide is preferably boron tribromide, and more preferably 1 to 1.5 times the theoretical reaction amount.
7. The method of claim 4, wherein R is selected from the group consisting of1MgX is 2,4, 6-trimethylbenzene magnesium bromide.
8. Use of the visible light driven boron doped photochromic material of any one of claims 1 to 3 in a reversible photochromic material under visible light drive;
preferably, it is used as a reversible photochromic material that is driven by visible light and has fluorescent emission.
9. Use according to claim 8, characterized in that the material is used for at least one of anti-counterfeiting, information storage, logic gates, lossless data read-out.
10. A visible light-driven boron doped photochromic device, which is characterized by comprising the visible light-driven photochromic material as claimed in any one of claims 1 to 3.
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| CN108083969A (en) * | 2017-12-21 | 2018-05-29 | 湖南大学 | Spiral shell indene compound and its preparation and application |
| CN109679644A (en) * | 2019-01-17 | 2019-04-26 | 安徽师范大学 | Vis/NIR Spectroscopy induced discoloration fluorescent dye, fluorine boron fluorescent dye of α-α dimerization and its preparation method and application |
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| JP2002069439A (en) * | 2000-08-30 | 2002-03-08 | Kyocera Corp | Photochromic thin film and method of producing it and optical function element using it |
| KR20030012090A (en) * | 2001-07-30 | 2003-02-12 | 한국화학연구원 | Diarylethene derivatives and the photochromic thin film using of them |
| JP2012056861A (en) * | 2010-09-07 | 2012-03-22 | Nara Institute Of Science & Technology | Photochromic compound, postscript type optical recording molecule material, display material, and fluorescence label material |
| CN108083969A (en) * | 2017-12-21 | 2018-05-29 | 湖南大学 | Spiral shell indene compound and its preparation and application |
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