CN102417460A - Bromine atom-containing branched stilbene singlet oxygen photosensitizer and synthesis and application thereof - Google Patents
Bromine atom-containing branched stilbene singlet oxygen photosensitizer and synthesis and application thereof Download PDFInfo
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- CN102417460A CN102417460A CN2011102767673A CN201110276767A CN102417460A CN 102417460 A CN102417460 A CN 102417460A CN 2011102767673 A CN2011102767673 A CN 2011102767673A CN 201110276767 A CN201110276767 A CN 201110276767A CN 102417460 A CN102417460 A CN 102417460A
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Abstract
A bromine atom-containing branched stilbene singlet oxygen photosensitizer belongs to the field of singlet oxygen photosensitizers, and a typical chemical structure general formula of the compound is as follows, wherein in the molecular structural formula, R1, R2, R3 ,R4, R5 represent hydrogen atom or bromine atom substituents, and at least one of R1, R2, R3 ,R4, R5 is a bromine atom substituent. Bromine atom-containing benzyl diethyl phosphate is obtained by a reaction of bromine atom-containing benzyl bromide and triethyl phosphate; and the bromine atom-containing branched stilbene singlet oxygen photosensitizer, which can generate singlet oxygen by sensitization under visible light, is prepared by allowing the bromine atom-containing benzyl diethyl phosphate to react with 4-(p- nitrostyrene)yl-4'-aldehyde-triphenylamine in a glass container under an alkaline condition.
Description
Technical field
The invention belongs to the photosensitizers field of creating singlet oxygen by using, particularly relate to one type of synthetic and application that contains the dendritic diphenylethylene creating singlet oxygen by using photosensitizers of bromine atoms.
Background technology
Since nineteen sixty was found creating singlet oxygen by using, the chemistry of creating singlet oxygen by using was paid close attention to biological research greatly, all relates to creating singlet oxygen by using like the photosensitized oxidation of organic molecule, many research work such as photodegradation of polymkeric substance.Compare with ground state oxygen, creating singlet oxygen by using can with many electron rich molecule generation selective reactions, product can be as material or medicinal intermediates.Particularly creating singlet oxygen by using plays an important role in bioprocess, can be used for optical dynamic therapy.The current photosensitizers that is used for creating singlet oxygen by using all is the common compound that absorbs near-ultraviolet light and visible light; Like porporino etc.; Because the restriction of excited state character, mainly be that the coefficient that passes through between being is difficult to regulation and control, it is not fine to make that their photoinductions produce the quantum yield of creating singlet oxygen by using.Darmanyan in 1992 and Foote etc. have confirmed that heavy atom such as bromine atoms can increase excited state passes through coefficient between being, molecular energy effectively generates excited triplet state, and can effectively produce creating singlet oxygen by using in photosensitization under the illumination.Exercise question is: " the sensitizing agent heavy atom produces the influence of efficient to creating singlet oxygen by using " (Effect of sensitizer heavy atoms on singlet oxygen generation efficiency); Journal of Physical Chemistry 1992,96:3723-3728 (physical chemistry magazine).Therefore the molecule that contains bromine atoms should have and high passes through coefficient between being, improves the formation of excited triplet state greatly, produces creating singlet oxygen by using thereby help photosensitization, but at present report to contain bromine atoms class sensitiser absorption wavelength short partially.
Summary of the invention
The objective of the invention is to deficiency, prepare the dendritic diphenylethylene creating singlet oxygen by using photosensitizers that contains bromine atoms, under radiation of visible light, can photosensitization produce creating singlet oxygen by using through easy method to above-mentioned prior art.
The dendritic diphenylethylene creating singlet oxygen by using photosensitizers that passes through to contain bromine atoms involved in the present invention, the typical chemical structure of general formula of its compound is following:
R in the molecular structural formula wherein
1, R
2, R
3, R
4, R
5Expression Wasserstoffatoms or bromine atoms substituting group, and R
1, R
2, R
3, R
4, R
5In have one at least for the bromine atoms substituting group.
The dendritic diphenylethylene creating singlet oxygen by using photosensitizers compound method that preparation contains bromine atoms may further comprise the steps:
(1) the first step: Bian bromine synthetic that contains bromine atoms
Reaction equation is:
R in the molecular structural formula wherein
1, R
2, R
3, R
4, R
5Expression Wasserstoffatoms or bromine atoms substituting group, and R
1, R
2, R
3, R
4, R
5In have one at least for the bromine atoms substituting group; NBS is the N-bromo-succinimide.
Concrete steps:
According to Takahito Itoh and H. K. Hall Jr at " macromole " (Macromolecules) 1990; 23; The 4879-4881 report, exercise question: 7-chloro-7-phenyl-8,8-dicyano Kui quinoline bismethane: one is the new initiator (7-chloro-7-phenyl-8 of cationoid polymerisation; 8-dicyanoquinodimethane. reported method A novel initiator for cationic polymerizations) is improved.The toluene that contains bromine atoms and N-bromo-succinimide (NBS) mix in three mouthfuls ground flask with mol ratio 1:1.2 ratio (molar weight that is the N-bromo-succinimide is 1.2 times of molar weight that contain the toluene of bromine atoms), add condensing works, at CCl
4The middle backflow 48 hours filtered, and solid is recrystallization in benzene/cyclohexane, filters and obtains crystal, and be subsequent use;
(2) second steps: benzyl diethyl phosphoric acid synthetic that contains bromine atoms
Reaction equation:
R in the molecular structural formula wherein
1, R
2, R
3, R
4, R
5Expression Wasserstoffatoms or bromine atoms substituting group, and R
1, R
2, R
3, R
4, R
5In have one at least for the bromine atoms substituting group.
Concrete steps:
The benzyl bromine that contains bromine atoms that the first step is made and triethyl-phosphite mix in three mouthfuls ground flask with mol ratio 1:5 ratio (molar weight that is triethyl-phosphite is five times of molar weight that contain the benzyl bromine of bromine atoms), at 130-160
0C stirred 6 hours, and decompression steams unnecessary triethyl-phosphite again, obtains white crystal, and is subsequent use;
R in the molecular structural formula wherein
1, R
2, R
3, R
4, R
5Expression Wasserstoffatoms or bromine atoms substituting group, and R
1, R
2, R
3, R
4, R
5In have one at least for the bromine atoms substituting group.
(3) the 3rd steps: dendritic diphenylethylene creating singlet oxygen by using photosensitizers synthetic that contains bromine atoms
Reaction equation is:
Concrete steps:
The second benzyl diethyl phosphoric acid (II) that contains bromine atoms that make of step and 4-(p-nitrophenyl ethene) base-4 '-aldehyde radical-triphenylamine (III) be mixed to join with mol ratio 2:1 (molar weight that promptly contains the benzyl diethyl phosphoric acid of bromine atoms is two times of molar weight of 4-(p-nitrophenyl ethene) base-4 '-aldehyde radical-triphenylamine) in three mouthfuls the ground flask; Add condensing works,, add the basic catalyst of mol ratio 1:2 then with the tetrahydrofuran solvent dissolving of 200-350 times of volume ratio; The molar weight that is basic catalyst is two times of molar weight that contain the benzyl diethyl phosphoric acid of bromine atoms; Return time 24 hours is removed THF under the decompression, uses dichloromethane extraction; And washing; Drying, with solvent revolve do after, adopt silicagel column to separate the compound that obtains claim 1.
Described basic catalyst is sodium hydride, sodium alkoxide, potassium alcoholate, Anhydrous potassium carbonate or their any mixture.
The present invention contains the dendritic diphenylethylene compounds of bromine atoms through preparation, can be used as the photosensitizers of creating singlet oxygen by using, and because its absorption bands is wide, and maximum absorption wavelength is at visible region, can with now all light source such as tungsten-iodine lamp, xenon lamp, Ar
+Laser apparatus etc. are complementary.Therefore, compound of the present invention can be used as the photosensitizers that under visible light illumination, produces creating singlet oxygen by using.
Concrete operations are following:
In the long horminess glass tube of 25cm; Adding with The compounds of this invention as the creating singlet oxygen by using photosensitizers; 2, the 3-dihydropyrane is as the mixing solutions of substrate, at room temperature with visible light source at a distance of 5cm; Logical oxygen illumination 8 hours obtains the photooxidation reaction product between creating singlet oxygen by using and the substrate through mass spectrometric detection
1Formic acid-4-oxo-butyl ester) and reaction product (title:
2(title: 5,6-dihydro-2
H-pyran-2-one), the photooxidation reaction formula is following:
In the above-mentioned prescription, described organic solvent comprises ester class, ethers, acetonitrile or their any miscellanys.
The dendritic diphenylethylene creating singlet oxygen by using photosensitizers that preparation involved in the present invention contains bromine atoms has following advantage:
(1) compound method of the dendritic diphenylethylene creating singlet oxygen by using photosensitizers that contains bromine atoms involved in the present invention and separation are simple, and raw material sources conveniently are easy to get, and productive rate is moderate.Wherein precursor contain the benzyl diethyl phosphoric acid of bromine atoms can be through conventional method preparation.
(2) the dendritic diphenylethylene creating singlet oxygen by using sensitiser absorption wave band that contains bromine atoms involved in the present invention covers broad.
(3) the creating singlet oxygen by using quantum yield of the dendritic diphenylethylene creating singlet oxygen by using photosensitizers that contains bromine atoms involved in the present invention is higher.
Description of drawings
Fig. 1. the embodiment of the invention 1 is 1 * 10
-5(4-(4-nitrostyrolene base)-triphenylamine is dissolved in absorbancy and the relation curve of wavelength in the benzene to the 4-of mol/L (4-bromostyrol base)-N-.
Fig. 2. the embodiment of the invention 2 is 1 * 10
-5(4-(4-nitrostyrolene base)-triphenylamine is dissolved in absorbancy and the relation curve of wavelength in the benzene to the 4-of mol/L (3,5-dibromo-benzene vinyl)-N-.
Fig. 3. the embodiment of the invention 3 is 1 * 10
-5(4-(4-nitrostyrolene base)-triphenylamine is dissolved in absorbancy and the relation curve of wavelength in the benzene to the 4-of mol/L (phenyl-pentabromide vinyl)-N-.
Fig. 4. the embodiment of the invention 4,5,6 and 2,3-dihydropyrane photosensitized oxidation reaction product
1(title: mass spectrum formic acid-4-oxo-butyl ester).
Fig. 5. the embodiment of the invention 4,5,6 and 2,3-dihydropyrane photosensitized oxidation reaction product
2(title: 5,6-dihydro-2
H-pyran-2-one) mass spectrum.
Embodiment
Below in conjunction with accompanying drawing and embodiment the present invention is described further as follows:
Embodiment 1
4-(the 4-bromostyrol base)-N-(mensuration of the synthetic and ultraviolet-visible absorption spectroscopy of 4-(4-nitrostyrolene base)-triphenylamine
Synthetic three steps of branch carry out:
(1) 4-bromo benzyl bromine is synthetic
(0.035mol, 6.00g) (0.042mol 7.48g) mixes in three mouthfuls ground flask 4-bromo toluene, adds condensing works, at CCl with N-bromo-succinimide (NBS)
4The middle backflow 48 hours filtered, and solid is recrystallization in benzene/cyclohexane, and filter and obtain crystal, productive rate 78%, subsequent use;
(2) 4-benzyl bromide diethyl phosphoric acid is synthetic
(0.012mol, 3.00g) (0.060mol 9.96g) mixes in there-necked flask the 4-bromo benzyl bromine that the first step is made, at 130-160 with triethyl-phosphite
0C stirred 6 hours down, and decompression steams unnecessary triethyl-phosphite again, obtains white crystal, and productive rate 94% is subsequent use;
(3) 4-(4-bromostyrol base)-N-(synthesizing of 4-(4-nitrostyrolene base)-triphenylamine
The 4-benzyl bromide diethyl phosphoric acid that second step was made (3.26mmol, 1.00g)-4 '-aldehyde radical-(1.63mmol 0.69g) mixes in three mouthfuls ground flask triphenylamine with 4-(p-nitrophenyl ethene) base; Add condensing works, then with the dissolving of 50ml tetrahydrofuran solvent, sodium methylate (6.52mmol; 0.35g) as basic catalyst, return time 24 hours is removed THF under the decompression; Use dichloromethane extraction, and washing, the anhydrous sodium sulfate drying organic layer.With solvent revolve do after, adopt silicagel column to separate to obtain the compound of being invented, productive rate 43%.
With 1 * 10
-5(4-(4-nitrostyrolene base)-triphenylamine is dissolved in the benzene 4-of mol/L (4-bromostyrol base)-N-, measures its ultraviolet-visible absorption spectroscopy, and as shown in Figure 1, its absorption bands is wide, and maximum absorption wavelength is at the 435nm place.
Embodiment 2
4-(3, the 5-dibromo-benzene vinyl)-N-(mensuration of the synthetic and ultraviolet-visible absorption spectroscopy of 4-(4-nitrostyrolene base)-triphenylamine
Synthetic three steps of branch carry out:
Synthesizing of (1) 3,5-dibrominated benzyl bromine
3, (0.024mol, 6.00g) (0.029mol 5.13g) mixes in three mouthfuls ground flask 5-dibrominated toluene, adds condensing works, at CCl with N-bromo-succinimide (NBS)
4The middle backflow 48 hours filtered, and solid is recrystallization in benzene/cyclohexane, and filter and obtain crystal, productive rate 76%, subsequent use;
Synthesizing of (2) 3,5-dibrominated benzyl diethyl phosphoric acids
With the first step make 3, (0.009mol, 3.00g) (0.045mol 7.48g) mixes in three mouthfuls ground flask, at 130-160 5-dibrominated benzyl bromine with triethyl-phosphite
0C stirred 6 hours, and decompression steams unnecessary triethyl-phosphite again, obtains white crystal, and productive rate 93% is subsequent use;
(3) 4-(3,5-dibromo-benzene vinyl)-N-(synthesizing of 4-(4-nitrostyrolene base)-triphenylamine
With second step make 3,5-dibrominated benzyl diethyl phosphoric acid (2.60mmol, 1.00g)-4 '-aldehyde radical-(1.30mmol 0.55g) mixes in three mouthfuls ground flask triphenylamine with 4-(p-nitrophenyl ethene) base; Add condensing works, then with the dissolving of 50ml tetrahydrofuran solvent, sodium methylate (5.20mmol; 0.28g) as basic catalyst, refluxed 24 hours, remove THF under the decompression; Use dichloromethane extraction, and washing, the anhydrous sodium sulfate drying organic layer.With solvent revolve do after, adopt silicagel column to separate to obtain the compound of being invented, productive rate 40%.
With 1 * 10
-5(4-(4-nitrostyrolene base)-triphenylamine is dissolved in the benzene 4-of mol/L (3,5-dibromo-benzene vinyl)-N-, measures its ultraviolet-visible absorption spectroscopy, and as shown in Figure 2, its absorption bands is wide, and maximum absorption wavelength is at the 430nm place.
Embodiment 3
4-(the phenyl-pentabromide vinyl)-N-(mensuration of the synthetic and ultraviolet-visible absorption spectroscopy of 4-(4-nitrostyrolene base)-triphenylamine
Synthetic three steps of branch carry out:
(1) pentabromo-Bian bromine is synthetic
(0.012mol, 6.00g) (0.014mol 2.56g) mixes in three mouthfuls ground flask pentabromotoluene, adds condensing works, at CCl with N-bromo-succinimide (NBS)
4The middle backflow 48 hours filtered, and solid is recrystallization in benzene/cyclohexane, and filter and obtain crystal, productive rate 77%, subsequent use;
(2) pentabromo-benzyl diethyl phosphoric acid is synthetic
(0.005mol, 3.00g) (0.025mol 4.15g) mixes in three mouthfuls ground flask, at 130-160 the pentabromo-Bian bromine that the first step is made with triethyl-phosphite
0C stirred 6 hours, and decompression steams unnecessary triethyl-phosphite again, obtains white crystal, and productive rate 95% is subsequent use;
(3) 4-(phenyl-pentabromide vinyl)-N-(synthesizing of 4-(4-nitrostyrolene base)-triphenylamine
The pentabromo-benzyl diethyl phosphoric acid that second step was made (1.60mmol, 1.00g)-4 '-aldehyde radical-(0.80mmol 0.34g) mixes in three mouthfuls ground flask triphenylamine with 4-(p-nitrophenyl ethene) base; Add condensing works, then with the dissolving of 50ml tetrahydrofuran solvent, sodium methylate (3.20 mmol; 1.73g) as basic catalyst, return time 24 hours is removed THF under the decompression; Use dichloromethane extraction, and washing, the anhydrous sodium sulfate drying organic layer.With solvent revolve do after, adopt silicagel column to separate to obtain the compound of being invented, productive rate 41%.
With 1 * 10
-5(4-(4-nitrostyrolene base)-triphenylamine is dissolved in the benzene 4-of mol/L (phenyl-pentabromide vinyl)-N-, measures its ultraviolet-visible absorption spectroscopy, and as shown in Figure 3, its absorption bands is wide, and maximum absorption wavelength is at the 430nm place.
Embodiment 4
(4-(4-nitrostyrolene base)-triphenylamine radiation of visible light produces creating singlet oxygen by using down to 4-(4-bromostyrol base)-N-
In the long horminess glass tube of 25cm, adding concentration is 1 * 10
-5(4-(4-nitrostyrolene base)-triphenylamine acetonitrile solution 15ml and concentration are 2 of 1mol/L to the 4-of mol/L (4-bromostyrol base)-N-; 3-dihydropyrane acetonitrile solution 5ml; At room temperature apart from visible light source 5cm; Logical oxygen illumination 8 hours is through the photooxidation reaction product of mass spectrometric detection affirmation creating singlet oxygen by using
1Formic acid-4-oxo-butyl ester) and reaction product (title:
2(title: 5,6-dihydro-2
H-pyran-2-one) generation.
Embodiment 5
(4-(4-nitrostyrolene base)-triphenylamine radiation of visible light produces creating singlet oxygen by using down to 4-(3,5-dibromo-benzene vinyl)-N-
In the long horminess glass tube of 25cm, adding concentration is 1 * 10
-5The 4-(3 of mol/L; 5-dibromo-benzene vinyl)-(4-(4-nitrostyrolene base)-triphenylamine acetonitrile solution 15ml and concentration are 2 of 1mol/L to N-; 3-dihydropyrane acetonitrile solution 5ml; At room temperature apart from visible light source 5cm, logical oxygen illumination 8 hours is through the photooxidation reaction product of mass spectrometric detection affirmation creating singlet oxygen by using
1Formic acid-4-oxo-butyl ester) and reaction product (title:
2(title: 5,6-dihydro-2
H-pyran-2-one) generation.
Embodiment 6
(4-(4-nitrostyrolene base)-triphenylamine radiation of visible light produces creating singlet oxygen by using down to 4-(phenyl-pentabromide vinyl)-N-
In the long horminess glass tube of 25cm, adding concentration is 1 * 10
-5(4-(4-nitrostyrolene base)-triphenylamine acetonitrile solution 15ml and concentration are 2 of 1mol/L to the 4-of mol/L (phenyl-pentabromide vinyl)-N-; 3-dihydropyrane acetonitrile solution 5ml; At room temperature apart from visible light source 5cm; Logical oxygen illumination 8 hours is through the photooxidation reaction product of mass spectrometric detection affirmation creating singlet oxygen by using
1Formic acid-4-oxo-butyl ester) and reaction product (title:
2(title: 5,6-dihydro-2
H-pyran-2-one) generation.
Claims (3)
1. contain the dendritic diphenylethylene creating singlet oxygen by using photosensitizers of bromine atoms, the typical chemical structure of general formula of its compound is:
R in the molecular structural formula wherein
1, R
2, R
3, R
4, R
5Expression Wasserstoffatoms or bromine atoms substituting group, and R
1, R
2, R
3, R
4, R
5In have one at least for the bromine atoms substituting group.
2. the described compound method that contains the dendritic diphenylethylene creating singlet oxygen by using photosensitizers of bromine atoms of claim 1
,It is characterized in that: step is following:
The first step: benzyl bromine synthetic that contains bromine atoms
The toluene that contains bromine atoms and N-bromo-succinimide (NBS) mix in three mouthfuls ground flask with mol ratio 1:1.2 ratio (molar weight that is the N-bromo-succinimide is 1.2 times of molar weight that contain the toluene of bromine atoms), add condensing works, at CCl
4The middle backflow 48 hours filtered, and solid is recrystallization in benzene/cyclohexane, filters and obtains crystal, and be subsequent use;
R in the molecular structural formula wherein
1, R
2, R
3, R
4, R
5Expression Wasserstoffatoms or bromine atoms substituting group, and R
1, R
2, R
3, R
4, R
5In have one at least for the bromine atoms substituting group;
Second step: benzyl diethyl phosphoric acid synthetic that contains bromine atoms
The benzyl bromine that contains bromine atoms that the first step is made and triethyl-phosphite mix in three mouthfuls ground flask with mol ratio 1:5 ratio (molar weight that is triethyl-phosphite is five times of molar weight that contain the benzyl bromine of bromine atoms), at 130-160
0C stirred 6 hours, and decompression steams unnecessary triethyl-phosphite again, obtains white crystal, and is subsequent use;
R in the molecular structural formula wherein
1, R
2, R
3, R
4, R
5Expression Wasserstoffatoms or bromine atoms substituting group, and R
1, R
2, R
3, R
4, R
5In have one at least for the bromine atoms substituting group;
The 3rd step: dendritic diphenylethylene creating singlet oxygen by using photosensitizers synthetic that contains bromine atoms
The second benzyl diethyl phosphoric acid (II) that contains bromine atoms that make of step and 4-(p-nitrophenyl ethene) base-4 '-aldehyde radical-triphenylamine (III) are mixed in three mouthfuls ground flask with mol ratio 2:1 ratio (molar weight that promptly contains the benzyl diethyl phosphoric acid of bromine atoms is two times of molar weight of basic-the 4 '-aldehyde radical of 4-(p-nitrophenyl ethene)-triphenylamine); Add condensing works,, add the basic catalyst of mol ratio 1:2 then with the tetrahydrofuran solvent dissolving of 200-350 times of volume ratio; The molar weight that is basic catalyst is two times of molar weight that contain the benzyl diethyl phosphoric acid of bromine atoms; Return time 24 hours is removed THF under the decompression, uses dichloromethane extraction; And washing; Drying, with solvent revolve do after, adopt silicagel column to separate the compound that obtains claim 1.
3. the dendritic diphenylethylene creating singlet oxygen by using photosensitizers that contains bromine atoms as claimed in claim 1 is characterized in that: purposes is that visible light is according to the photosensitizers that produces creating singlet oxygen by using.
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Cited By (1)
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| CN103242133A (en) * | 2013-04-15 | 2013-08-14 | 西安近代化学研究所 | Synthesis method of 4-[2-(trans-4-alkylcyclohexyl)ethyl] bromobenzene |
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Application publication date: 20120418 |