CN101838475A - P-nitryl diphenylethylene dye sensitizing agent containing bromine as well as synthesis and application thereof - Google Patents
P-nitryl diphenylethylene dye sensitizing agent containing bromine as well as synthesis and application thereof Download PDFInfo
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- CN101838475A CN101838475A CN 201010185136 CN201010185136A CN101838475A CN 101838475 A CN101838475 A CN 101838475A CN 201010185136 CN201010185136 CN 201010185136 CN 201010185136 A CN201010185136 A CN 201010185136A CN 101838475 A CN101838475 A CN 101838475A
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- nitryl
- diphenylethylene
- sensitizing agent
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Abstract
The invention relates to a P-nitryl diphenylethylene dye sensitizing agent containing bromine as well as synthesis and application thereof, belonging to the field of singlet oxygen sensitizing agents. A compound of the P-nitryl diphenylethylene dye sensitizing agent has a typical chemical structural formula shown in the structural formula, wherein R1, R2, R3, R4 and R5 in a molecular structural formula represent a hydrogen atom substituent group or a bromine atom substituent group, and at least one of the R1, R2, R3, R4 and R5 is the bromine atom substituent group. Benzyl bromine containing the bromine is added into a glass container to react with 3',4'-dyhydroxyl-4-nitryl diphenylethylene under the alkali condition to prepare the P-nitryl diphenylethylene dye containing bromine which can be sensitized under the irradiation of near ultraviolet and visible light to generate singlet oxygen.
Description
Technical field
The invention belongs to creating singlet oxygen by using sensitizing agent field, particularly bromated synthetic and application to the nitro toluylene dyestuff.
Background technology
Creating singlet oxygen by using occupies extremely important status in photochemistry, photo bio, polymer science.Darmany A.P. in 1992 and Foote C.S. at exercise question are: " the sensitizing agent heavy atom produces the influence of efficient to creating singlet oxygen by using " (Effect ofsensitizer heavy atoms on singlet oxygen generation efficiency), Journal of PhysicalChemistry 1992, confirmed in 96:3723-3728 (physical chemistry magazine) paper that heavy atom can increase excited state be between pass through coefficient, molecular energy effectively generates excited triplet state.Contain the heavy atom molecule and rail takes place easily when excited state revolve coupling and interact, increased the efficient that is converted into triplet state by singlet state, pass through efficient between promptly being, this phenomenon is called " heavy atoms effect ".Yet the general absorption bands covering of creating singlet oxygen by using sensitizing agent that contains heavy atom at present is narrower, and perhaps synthetic method is complicated, and productive rate is lower, and the creating singlet oxygen by using quantum yield that produces when being used for sensitization ground state oxygen is lower.
Summary of the invention
The objective of the invention is at above-mentioned the deficiencies in the prior art, prepare bromatedly by easy method, can photosensitization under near ultraviolet and radiation of visible light produce creating singlet oxygen by using nitryl diphenylethylene dye sensitizing agent.
Involved in the present invention is bromated to nitro toluylene creating singlet oxygen by using sensitizing agent, and the typical chemical structure of general formula of its compound is as follows:
R in the molecular structural formula wherein
1, R
2, R
3, R
4, R
5All represent hydrogen atom 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.
Above-mentioned bromated synthetic method to nitro toluylene creating singlet oxygen by using sensitizing agent may further comprise the steps:
(1) contains the bromination of toluene bromide
Reaction equation is:
Concrete steps are as follows:
Contain toluene bromide and mix in three mouthfuls ground flask with 1: 1 ratio of mol ratio, add condensing works, at CCl with N-bromo-succinimide (NBS)
4The middle backflow 36 to 72 hours filtered, and solid is recrystallization in benzene/cyclohexane, filters and obtains crystal, and be standby.
(2) 3,4-dihydroxyl-synthesizing to nitro diphenyl ethylene
Concrete steps are as follows:
Add paranitrophenylacetic acid, 3 in there-necked flask, 4-Dihydroxy benzaldehyde and hexahydropyridine are heated to 100 ℃ of reactions 3-4 hour, produce until no bubble.Be warmed up to 130 ℃ then, continue reaction 2 hours.Reactant obtains the brownish black solid, drying for standby with hot dehydrated alcohol recrystallization 2 times.
(3) bromated synthesizing to nitro toluylene creating singlet oxygen by using sensitizing agent
Reaction equation is:
Concrete steps are as follows:
With second the step gained 3 '; 4 '-dihydroxyl-4-nitro diphenyl ethylene and the corresponding brominated product of the first step gained join with mol ratio in three mouthfuls the ground flask and mix at 1: 6; use an amount of exsiccant acetone solution then respectively; add 1: 6 basic catalyst of mol ratio; added phase-transfer catalyst hexaoxacyclooctadecane-6-6 again in 1: 0.05 in molar ratio; room temperature reaction is 48 hours under argon shield; reaction finishes the concentrated acetone of removing in back; again dissolve with methylene dichloride; add the water extraction; get the organic layer anhydrous sodium sulfate drying; remove by filter siccative; solution concentration is dissolved with an amount of benzene and hexanaphthene, and silicagel column separates, and gets yellow solid with benzene and hexanaphthene recrystallization again.
Among the bromated preparation method to nitro toluylene creating singlet oxygen by using sensitizing agent involved in the present invention, the 3rd step, described basic catalyst was sodium alkoxide, sodium hydroxide, Anhydrous potassium carbonate etc. or their any mixture.
Of the present invention bromated to the nitro toluylene compound by preparation, can be used as the sensitizing agent of creating singlet oxygen by using, and because its absorption bands is wide, and absorbing wavelength is near ultraviolet and 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 sensitizing agent that produces creating singlet oxygen by using under near ultraviolet and visible light condition.
Concrete operations are as follows:
In the long horminess glass tube of 25cm, be sensitizing agent with the The compounds of this invention, vinyl monomer at room temperature uses near ultraviolet and visible light source apart from 5cm as substrate, logical oxygen illumination 3 hours, check obtains the creating singlet oxygen by using reaction product.
Bromated sensitizing agent to the nitro toluylene creating singlet oxygen by using involved in the present invention has following advantage:
(1) bromated synthetic method and separation to the nitro toluylene sensitizing agent of the present invention is simple, and raw material sources conveniently are easy to get.Wherein precursor contain bromobenzyl bromine and 3 ', 4 '-dihydroxyl-4-nitro diphenyl ethylene compound all can be by conventional method preparation.With the two condensation under alkaline condition, just can make bromated sensitizing agent of the present invention, and productive rate is higher then to nitro toluylene.
(2) of the present invention bromated to nitro toluylene creating singlet oxygen by using sensitizing agent absorption bands covering broad.
(3) the bromated creating singlet oxygen by using quantum yield height that nitro toluylene creating singlet oxygen by using sensitizing agent is used for the generation of sensitization oxygen of the present invention.
Description of drawings
Fig. 1. 3 of the embodiment of the invention 4 ', 4 '-two (4 " bromobenzene inferior methoxyl group)-4-nitro diphenyl ethylene is dissolved in the relation curve of absorbancy and wavelength in the methylene dichloride.
Fig. 2. 3 of the embodiment of the invention 5 ', 4 '-two (the inferior methoxyl group of 3 ", 5 " dibromo-benzene)-4-nitro diphenyl ethylenes are dissolved in the relation curve of absorbancy and wavelength in the methylene dichloride.
Fig. 3. 3 of the embodiment of the invention 6 ', 4 '-two (2 ", 3 ", 4 ", 5 ", 6 " the inferior methoxyl group of phenyl-pentabromide)-4-nitro diphenyl ethylene is dissolved in the relation curve of absorbancy and wavelength in the methylene dichloride.
Embodiment
Embodiment 1
3 ', 4 '-two (4 " bromobenzene inferior methoxyl group)-4-nitro diphenyl ethylene synthetic
Divided for three steps carried out:
(1) 4-bromobenzyl bromine is synthetic
1.69 gram 4-toluene bromide in three mouthful ground flask mixes with mol ratio with 1.78 gram N-bromo-succinimides (NBS) at 1: 1, adds condensing works, at CCl
4The middle backflow 36 hours filtered, and solid is recrystallization in benzene/cyclohexane, and filter and obtain crystal, productive rate 90%, standby.
(2) 3 ', 4 '-dihydroxyl-4-nitro diphenyl ethylene synthetic
In there-necked flask, add compound paranitrophenylacetic acid (5.0g), 3,4-Dihydroxy benzaldehyde (5.7g) and hexahydropyridine (4.1ml) (paranitrophenylacetic acid: 3, the 4-Dihydroxy benzaldehyde: hexahydropyridine is 1: 1.5: 1.5) mix, be heated to 100 ℃ of back flow reaction 3-4 hours, and produced until no bubble.Be warmed up to 130 ℃ then, continue reaction 2 hours.Reactant obtains target compound (5.0g), productive rate 70% with hot dehydrated alcohol recrystallization 2 times.
(3) 3 ', 4 '-two (4 " bromobenzene inferior methoxyl group)-4-nitro diphenyl ethylene synthetic
Adding compound 3 in there-necked flask '; 4 '-dihydroxyl-4-nitro diphenyl ethylene (0.256g), 4-bromobenzyl bromine (1.482g), salt of wormwood (0.828g) (3 '; 4 '-dihydroxyl-4-nitro diphenyl ethylene: 4-bromobenzyl bromine: salt of wormwood is 1: 6: 6) mix; then with an amount of dry acetone dissolving; add phase-transfer catalyst hexaoxacyclooctadecane-6-6 (0.02g) again, room temperature reaction is 48 hours under argon shield.Concentrate after reaction finishes and remove acetone, dissolve again, add the water extraction with methylene dichloride, get the organic layer anhydrous sodium sulfate drying, remove by filter siccative, solution concentration is dissolved with an amount of benzene and hexanaphthene, silicagel column separates, and gets yellow solid with benzene and hexanaphthene recrystallization again, productive rate 50%.
Embodiment 2
3 ', 4 '-two (3 ", 5 " the inferior methoxyl group of dibromo-benzene)-synthesizing of 4-nitro diphenyl ethylene divided for three steps carried out:
Synthesizing of (1) 3,5-two bromo benzyl bromines
2.499 restrain 3,5-two bromo toluene in three mouthful ground flask mix with mol ratio with 1.78 gram N-bromo-succinimides (NBS) at 1: 1, add condensing works, at CCl
4The middle backflow 48 hours filtered, and solid is recrystallization in benzene/cyclohexane, and filter and obtain crystal, productive rate 90%, standby;
(2) 3 ', 4 '-dihydroxyl-4-nitro diphenyl ethylene synthetic
Synthetic pressing second step among the embodiment 1;
(3) 3 ', 4 '-two (the inferior methoxyl group of 3 ", 5 " dibromo-benzene)-4-nitro diphenyl ethylenes synthetic
Adding compound 3 in there-necked flask '; 4 '-dihydroxyl-4-nitro diphenyl ethylene (0.256g), 3; 5-two bromo benzyl bromines (1.967g), salt of wormwood (0.828g) (3 '; 4 '-dihydroxyl-4-nitro diphenyl ethylene: 3; 5-two bromo benzyl bromines: salt of wormwood is 1: 6: 6) mix; with an amount of dry acetone dissolving, add phase-transfer catalyst hexaoxacyclooctadecane-6-6 (0.02g) more then, room temperature reaction is 48 hours under argon shield.Concentrate after reaction finishes and remove acetone, dissolve again, add the water extraction with methylene dichloride, get the organic layer anhydrous sodium sulfate drying, remove by filter siccative, solution concentration is dissolved with an amount of benzene and hexanaphthene, silicagel column separates, and gets yellow solid with benzene and hexanaphthene recrystallization again, productive rate 40%.
Embodiment 3
3 ', 4 '-two (2 ", 3 ", 4 " and, 5 ", 6 " and the inferior methoxyl group of phenyl-pentabromide)-synthesizing of 4-nitro diphenyl ethylene divided for three steps carried out:
(1) 2,3,4,5,6-pentabromo-benzyl bromine synthetic
5 grams 2,3,4,5,6-pentabromo-toluene in three mouthful ground flask mixes with mol ratio with 1.78 gram N-bromo-succinimides (NBS) at 1: 1, adds condensing works, at CCl
4The middle backflow 72 hours filtered, and solid is recrystallization in benzene/cyclohexane, and filter and obtain crystal, productive rate 60%, standby;
3 (2)) ', 4 '-dihydroxyl-4-nitro diphenyl ethylene synthetic
Synthetic pressing second step among the embodiment 1;
(3) 3 ', 4 '-two (2 ', 3 ', 4 ', 5 ', 6 '-the inferior methoxyl group of phenyl-pentabromide)-4-nitro diphenyl ethylene synthetic
Adding compound 3 in there-necked flask ', 4 '-dihydroxyl-4-nitro diphenyl ethylene (0.256g), 2,3; 4,5,6-pentabromo-benzyl bromine (3.366g), salt of wormwood (0.828g) (3 '; 4 '-dihydroxyl-4-nitro diphenyl ethylene: 2; 3,4,5; 6-pentabromo-benzyl bromine: salt of wormwood is 1: 6: 6) mix; with an amount of dry acetone dissolving, add phase-transfer catalyst hexaoxacyclooctadecane-6-6 (0.02g) more then, room temperature reaction is 48 hours under argon shield.Concentrate after reaction finishes and remove acetone, dissolve again, add the water extraction with methylene dichloride, get the organic layer anhydrous sodium sulfate drying, remove by filter siccative, solution concentration is dissolved with an amount of benzene and hexanaphthene, silicagel column separates, and gets yellow solid with benzene and hexanaphthene recrystallization again, productive rate 35%.
Embodiment 4
With 1 * 10
-53 of mol/L ', 4 '-two (4 " bromobenzene inferior methoxyl group)-4-nitro diphenyl ethylene is dissolved in the methylene dichloride, measures its ultraviolet-visible absorption spectroscopy, as Fig. 1.
Embodiment 5
With 1 * 10
-53 of mol/L ', 4 '-two (the inferior methoxyl group of 3 ", 5 " dibromo-benzene)-4-nitro diphenyl ethylenes are dissolved in the methylene dichloride, measure its ultraviolet-visible absorption spectroscopy, as Fig. 2.
Embodiment 6
With 1 * 10
-53 of mol/L ', 4 '-two (2 ", 3 ", 4 ", 5 ", 6 " the inferior methoxyl group of phenyl-pentabromide)-4-nitro diphenyl ethylene is dissolved in the methylene dichloride, measures its ultraviolet-visible absorption spectroscopy, as Fig. 3.
Embodiment 7
3 ', 4 '-two (4 " the bromobenzene benzyloxy)-4-nitro diphenyl ethylene near ultraviolet and the following creating singlet oxygen by using that produces of radiation of visible light
In the long horminess glass tube of 25cm, add 1mol/L3 ', 4 '-two (4 " bromobenzene inferior methoxyl group)-dichloromethane solution 15ml of 4-nitro diphenyl ethylene and the vinylbenzene of 5ml; under the room temperature apart near ultraviolet light source and visible light source 5cm; logical oxygen illumination 3 hours, by the generation of gas chromatography mass spectrometry with the photo-oxidation product phenyl aldehyde of nucleus magnetic hydrogen spectrum check affirmation creating singlet oxygen by using.
Embodiment 8
3 ', 4 '-two (3 ", 5 " the inferior methoxyl group of dibromo-benzene)-4-nitro diphenyl ethylene near ultraviolet and the following creating singlet oxygen by using that produces of radiation of visible light
In the long horminess glass tube of 25cm, add 1mol/L3 ', 4 '-two (3 "; 5 " the inferior methoxyl group of-dibromo-benzene)-the dichloromethane solution 15ml of 4-nitro diphenyl ethylene and the vinylbenzene of 5ml, under the room temperature apart near ultraviolet light source and visible light source 5cm, the generation of the photo-oxidation product phenyl aldehyde of creating singlet oxygen by using is confirmed in logical oxygen illumination 3 hours by gas chromatography mass spectrometry and nucleus magnetic hydrogen spectrum check.
Embodiment 9
3 ', 4 '-two (2 ", 3 ", 4 " and, 5 ", 6 " and the inferior methoxyl group of phenyl-pentabromide)-4-nitro diphenyl ethylene near ultraviolet and the following creating singlet oxygen by using that produces of radiation of visible light
In the long horminess glass tube of 25cm, add 1mol/L3 ', 4 '-two (2 "; 3 ", 4 ", 5 ", 6 " the inferior methoxyl group of phenyl-pentabromide)-and the dichloromethane solution 15ml of 4-nitro diphenyl ethylene and the vinylbenzene of 5ml; at room temperature apart near ultraviolet light source and visible light source 5cm, logical oxygen illumination 3 hours is by the generation of gas chromatography mass spectrometry with the photo-oxidation product phenyl aldehyde of nucleus magnetic hydrogen spectrum check affirmation creating singlet oxygen by using.
Claims (3)
- One kind bromated to nitryl diphenylethylene dye sensitizing agent, 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 5All represent hydrogen atom 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. one kind prepares the described bromated synthetic method to nitryl diphenylethylene dye sensitizing agent of claim 1, it is characterized in that step is as follows:The first step: contain the synthetic of bromobenzyl bromineBromated toluene mixes in three mouthfuls ground flask with 1: 1 ratio of mol ratio with N-bromo-succinimide (NBS), adds condensing works, at CCl 4The middle backflow 36 to 72 hours filtered, and solid is recrystallization in benzene/cyclohexane, filters and obtains crystal, and be standby;Reaction equation:
R in the molecular structural formula wherein 1, R 2, R 3, R 4, R 5All represent hydrogen atom 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: 3 ', 4 '-preparation of dihydroxyl-4-nitro diphenyl ethyleneBe 1: 1.5: 1.5 adding paranitrophenylacetic acid, 3 in molar ratio in there-necked flask, 4-Dihydroxy benzaldehyde and hexahydropyridine, be heated to 100 ℃ of reactions 3-4 hour, produce until no bubble, be warmed up to 130 ℃ then, continue reaction 2 hours, reactant is with hot dehydrated alcohol recrystallization 2 times, obtain the brownish black solid, drying for standby;The 3rd step: bromated synthesizing to nitryl diphenylethylene dye sensitizing agentWith 3 ' of the second step gained; 4 '-dihydroxyl-4-nitro diphenyl ethylene and the corresponding brominated product of the first step gained join with mol ratio in three mouthfuls the ground flask at 1: 6 mixes; use an amount of exsiccant acetone solution then respectively; add 1: 6 basic catalyst of mol ratio; added phase-transfer catalyst hexaoxacyclooctadecane-6-6 again in 1: 0.05 in molar ratio; room temperature reaction is 48 hours under argon shield; reaction finishes the concentrated acetone of removing in back; again dissolve with methylene dichloride; add the water extraction; get the organic layer anhydrous sodium sulfate drying; remove by filter siccative, solution concentration is dissolved with an amount of benzene and hexanaphthene, silicagel column separates; the yellow solid that obtains with benzene and hexanaphthene recrystallization is bromated to nitryl diphenylethylene dye sensitizing agent again. - 3. a claim 1 is bromated to nitryl diphenylethylene dye sensitizing agent, and its purposes is: as the photosensitizer that produces creating singlet oxygen by using.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102417460A (en) * | 2011-09-19 | 2012-04-18 | 重庆大学 | Bromine atom-containing branched stilbene singlet oxygen photosensitizer and synthesis and application thereof |
| CN102516084A (en) * | 2011-10-08 | 2012-06-27 | 重庆大学 | Straight chain type para nitro toluylene photosencitizer containing bromine atoms, synthesis and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101220212A (en) * | 2007-12-17 | 2008-07-16 | 重庆大学 | Diphenyl ketone containing nitryl stilbene dye formed with ester linkage, synthesis and application thereof |
| CN101367890A (en) * | 2008-10-16 | 2009-02-18 | 重庆大学 | Para nitro toluylene visible light photosencitizer, synthesis and uses thereof |
| CN101440038A (en) * | 2008-11-17 | 2009-05-27 | 重庆大学 | Polybrominated diphenyl ethylene dye sensitizing agent, synthesis and use thereof |
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2010
- 2010-05-28 CN CN 201010185136 patent/CN101838475A/en active Pending
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| CN101220212A (en) * | 2007-12-17 | 2008-07-16 | 重庆大学 | Diphenyl ketone containing nitryl stilbene dye formed with ester linkage, synthesis and application thereof |
| CN101367890A (en) * | 2008-10-16 | 2009-02-18 | 重庆大学 | Para nitro toluylene visible light photosencitizer, synthesis and uses thereof |
| CN101440038A (en) * | 2008-11-17 | 2009-05-27 | 重庆大学 | Polybrominated diphenyl ethylene dye sensitizing agent, synthesis and use thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102417460A (en) * | 2011-09-19 | 2012-04-18 | 重庆大学 | Bromine atom-containing branched stilbene singlet oxygen photosensitizer and synthesis and application thereof |
| CN102516084A (en) * | 2011-10-08 | 2012-06-27 | 重庆大学 | Straight chain type para nitro toluylene photosencitizer containing bromine atoms, synthesis and application thereof |
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Application publication date: 20100922 |