CN102516084A - Straight chain type para nitro toluylene photosencitizer containing bromine atoms, synthesis and application thereof - Google Patents

Straight chain type para nitro toluylene photosencitizer containing bromine atoms, synthesis and application thereof Download PDF

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CN102516084A
CN102516084A CN2011102932242A CN201110293224A CN102516084A CN 102516084 A CN102516084 A CN 102516084A CN 2011102932242 A CN2011102932242 A CN 2011102932242A CN 201110293224 A CN201110293224 A CN 201110293224A CN 102516084 A CN102516084 A CN 102516084A
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bromine atoms
nitro
toluylene
straight chain
chain type
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柳猛
李红茹
高放
张雪萍
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Chongqing University
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Abstract

The invention relates to a straight chain type para nitro toluylene photosencitizer containing bromine atoms, synthesis and application thereof, which belongs to the singlet oxygen photosencitizer field. A typical chemical structural formula is shown in a following graph: wherein R1, R2, R3, R4 and R5 in the molecular structure represent hydrogen atoms or bromine atom substituent, and at least one of R1, R2, R3, R4 and R5 is the bromine atom substituent. The benzyl bromide containing bromine atoms is reacted with 4-hydroxyl-4'- nitro toluylene under the alkaline condition, and the straight chain type para nitro toluylene photosencitizer containing bromine atoms is prepared, the straight chain type para nitro toluylene photosencitizer of the invention is capable of sensitizing and generating singlet oxygen under illumination of the visible light.

Description

Straight chain type contain bromine atoms to nitro toluylene photosensitizers and synthetic and application
Technical field
The invention belongs to creating singlet oxygen by using photosensitizers field, particularly straight chain type contain bromine atoms to the synthetic of nitro toluylene photosensitizers dyestuff and use.
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 sensitizing agent 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 can be with 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.The present invention contains the dendritic diphenylethylene creating singlet oxygen by using sensitizing agent of bromine atoms through preparation, under visible light illumination, can photosensitization produce creating singlet oxygen by using.
The general absorption bands of the creating singlet oxygen by using sensitizing agent of being reported at present covers narrower, and perhaps compound method is complicated, and productive rate is lower.
Summary of the invention
The invention reside in deficiency to above-mentioned background technology, through easy method prepare straight chain type contain bromine atoms to the nitro toluylene photosensitizers, it can photosensitization generation creating singlet oxygen by using under radiation of visible light.
Straight chain type involved in the present invention contain bromine atoms to the nitro toluylene photosensitizers, the typical chemical structure of general formula of its compound is following:
Figure 158030DEST_PATH_IMAGE001
R in the molecular structural formula wherein 1, R 2, R 3, R 4, R 5Represent Wasserstoffatoms or bromine atoms substituting group, and R 1, R 2, R 3, R 4, R 5In have at least one to be that bromine atoms replaces.
The compound method to the nitro toluylene photosensitizers that above-mentioned straight chain type contains bromine atoms may further comprise the steps:
(1) the first step: benzyl bromine synthetic that contains bromine atoms
Reaction equation is:
Figure 356930DEST_PATH_IMAGE002
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 1:1.1 (molar weight that is the N-bromo-succinimide is 1.1 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) straight chain type contains the synthesizing the nitro toluylene photosensitizers of bromine atoms
Reaction equation is:
Figure 150443DEST_PATH_IMAGE003
R in the molecular structural formula wherein 1, R 2, R 3, R 4, R 5Represent 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:
4-hydroxyl-4'-nitro diphenyl ethylene is joined in the ground-in three-necked flask exsiccant acetone solution with 200-350 times of volume ratio, and argon shield adds the basic catalyst of mol ratio 1:2; The molar weight that is basic catalyst is 2 times of molar weight of 4-hydroxyl-4'-nitro diphenyl ethylene, and normal-temperature reaction 10 minutes adds the hexaoxacyclooctadecane-6 that mol ratio is 20:1-6 again; 20 times of hexaoxacyclooctadecane-6-6 molar weight that the molar weight that is 4-hydroxyl-4'-nitro diphenyl ethylene is contain the bromobenzyl bromine with mol ratio 2:1 with the first step gained at last, and the molar weight that promptly contains the bromobenzyl bromine is 2 times of molar weight of 4-hydroxyl-4'-nitro diphenyl ethylene; Join in the ground-in three-necked flask, room temperature reaction 24 hours, reaction finishes to remove acetone under the decompression of back; Again dissolve with trichloromethane, add the deionized water extraction, collected organic layer is used anhydrous magnesium sulfate drying; Remove by filter siccative; Solution decompression is concentrated with benzene and chloroform recrystallization 2 times, obtain yellow solid, be the compound of claim 1.
Described basic catalyst is sodium hydride, sodium alkoxide, potassium alcoholate, Anhydrous potassium carbonate or their any mixture.
The present invention through the preparation straight chain type contain bromine atoms to the nitro toluylene photosensitizer compounds; 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:
Figure 268440DEST_PATH_IMAGE004
In the above-mentioned prescription, described organic solvent comprises ester class, ethers, acetonitrile or their any miscellanys.
What straight chain type involved in the present invention contained bromine atoms has following advantage to quick dose of nitro toluylene light:
(1) straight chain type of the present invention contain bromine atoms to quick dose compound method of nitro toluylene light and separate simply, raw material sources conveniently are easy to get, and productive rate is higher.
What (2) straight chain type of the present invention contained bromine atoms absorbs phase of wave to broad to quick dose of nitro toluylene light.
What (3) straight chain type of the present invention contained bromine atoms can produce creating singlet oxygen by using to the nitro toluylene photosensitizers effectively under visible light illumination.
Description of drawings
Fig. 1. the embodiment of the invention 1,4'-(the inferior methoxyl group of 4''-bromobenzene)-4-nitro diphenyl ethylene is dissolved in N, and (concentration is 1 * 10 to dinethylformamide -5Mol/L) relation curve of absorbancy and wavelength in.
Fig. 2. the 4'-of the embodiment of the invention 2 (3'', the inferior methoxyl group of 5''-dibromo-benzene)-4-nitro diphenyl ethylene is dissolved in N, and (concentration is 1 * 10 to dinethylformamide -5Mol/L) relation curve of absorbancy and wavelength in.
Fig. 3. the 4'-of the embodiment of the invention 3 (2'', 3'', 4'', 5'', the inferior methoxyl group of 6''-phenyl-pentabromide)-4-nitro diphenyl ethylene is dissolved in N, and (concentration is 1 * 10 to dinethylformamide -5Mol/L) relation curve of absorbancy and wavelength in.
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 2The mass spectrum of (title: 5,6-dihydro-2H-pyran-2-one).
Embodiment
Below in conjunction with accompanying drawing and embodiment the present invention is described further as follows:
Embodiment 1
The mensuration of the synthetic and ultraviolet-visible absorption spectroscopy of 4'-(the inferior methoxyl group of 4''-bromobenzene)-4-nitro diphenyl ethylene
Synthetic two steps of branch carry out:
(1) 4-bromobenzyl bromine is synthetic
With 3.5g (20.6mmol) 4-toluene bromide and 4.05g (22.7mmol) N-bromo-succinimide (NBS), join successively in the ground-in three-necked flask and mix, at CCl 4The middle backflow 48 hours, cold filtration, filtrating is revolved dried, and with recrystallization in benzene/cyclohexane, filter and obtain white crystal, productive rate 91%, subsequent use;
(2) 4'-(the inferior methoxyl group of 4''-bromobenzene)-4-nitro diphenyl ethylene is synthetic
4-hydroxyl-4'-nitro diphenyl ethylene 0.3g (1.25mmol) is joined in the ground-in three-necked flask with the dissolving of 50ml dry acetone, and argon shield adds salt of wormwood 0.35g (2.5mmol); Normal-temperature reaction 10 minutes adds 0.0165g (0.0625mmol) hexaoxacyclooctadecane-6-6 again, at last 4-bromobenzyl bromine 0.62g (2.5mmol) is joined in the ground-in three-necked flask; Room temperature reaction 24 hours, reaction finish to remove acetone under the decompression of back, dissolve again with trichloromethane; Add the deionized water extraction, collected organic layer is used anhydrous magnesium sulfate drying, removes by filter siccative; Solution decompression is concentrated with benzene and chloroform recrystallization 2 times, obtain yellow solid, productive rate 65%.
With 1 * 10 -5The 4'-of mol/L (the inferior methoxyl group of 4''-bromobenzene)-4-nitro diphenyl ethylene is dissolved in N, in the dinethylformamide, measures its ultraviolet-visible absorption spectroscopy, and as shown in Figure 1, its absorption bands is wide, and maximum absorption wavelength is at the 380nm place.
Embodiment 2
The mensuration of the synthetic and ultraviolet-visible absorption spectroscopy of 4'-(3'', the inferior methoxyl group of 5''-dibromo-benzene)-4-nitro diphenyl ethylene
Synthetic two steps of branch carry out:
Synthesizing of (1) 3,5-dibrominated benzyl bromine
With 5g (20.1mmol) 3,5-dibrominated toluene and 3.6g (22.1mmol) N-bromo-succinimide (NBS) joins in the ground-in three-necked flask, at CCl successively 4The middle backflow 48 hours filtered, and solid is recrystallization in benzene/cyclohexane, and filter and obtain white crystal, productive rate 90%, subsequent use.
(2) 4'-(3'', the inferior methoxyl group of 5''-dibromo-benzene)-4-nitro diphenyl ethylene is synthetic
4'-hydroxyl-4-nitro diphenyl ethylene 0.24g (1mmol) is joined in the ground-in three-necked flask with the dissolving of 50ml dry acetone, and argon shield adds salt of wormwood 0.276g (2mmol), normal-temperature reaction 10 minutes; Add 0.0132g (0.05mmol) hexaoxacyclooctadecane-6-6 again, at last with 3,5-dibrominated benzyl bromine 0.66g (2mmol) joins in the ground-in three-necked flask; Room temperature reaction 24 hours, reaction finish to remove acetone under the decompression of back, dissolve again with trichloromethane; Add the deionized water extraction, collected organic layer is used anhydrous magnesium sulfate drying, removes by filter siccative; Solution decompression is concentrated with benzene and chloroform recrystallization 2 times, obtain yellow solid, productive rate 62%.
With 1 * 10 -5The 4'-of mol/L (3'', the inferior methoxyl group of 5''-dibromo-benzene)-4-nitro diphenyl ethylene is dissolved in N, in the dinethylformamide, measures its ultraviolet-visible absorption spectroscopy, and as shown in Figure 2, its absorption bands is wide, and maximum absorption wavelength is at the 380nm place.
Embodiment 3
The mensuration of the synthetic and ultraviolet-visible absorption spectroscopy of 4'-(2', 3', 4', 5', the inferior methoxyl group of 6'-phenyl-pentabromide)-4-nitro diphenyl ethylene
Synthetic two steps of branch carry out:
(1) 2,3,4,5,6-pentabromo-benzyl bromine synthetic
With 5g (10.4mmol) 2,3,4,5,6-pentabromo-toluene and 2.03g (11.4mmol) N-bromo-succinimide (NBS) joins successively in the ground-in three-necked flask and mixes, at CCl 4The middle backflow 72 hours filtered, and solid is recrystallization in benzene/cyclohexane, and filter and obtain white crystal, productive rate 72%, subsequent use.
(2) 4'-(2', 3', 4', 5', the inferior methoxyl group of 6'-phenyl-pentabromide)-4-nitro diphenyl ethylene is synthetic
4'-hydroxyl-4-nitro diphenyl ethylene 0.3g (1.25mmol) is joined in the ground-in three-necked flask with the dissolving of 50ml dry acetone, and argon shield adds salt of wormwood 0.35g (2.50mmol), normal-temperature reaction 10 minutes; Add 0.0165g (0.0625mmol) hexaoxacyclooctadecane-6-6 again, at last with 2,3; 4,5,6-pentabromo-benzyl bromine 1.42g (2.50mmol) joins in the ground-in three-necked flask; Room temperature reaction 24 hours, reaction finish to remove acetone under the decompression of back, dissolve again with trichloromethane; Add the deionized water extraction, collected organic layer is used anhydrous magnesium sulfate drying, removes by filter siccative; Solution decompression is concentrated with benzene and chloroform recrystallization 2 times, obtain yellow solid, productive rate 75%.
4'-(2', 3', 4', 5', the inferior methoxyl group of 6'-phenyl-pentabromide)-4-nitro diphenyl ethylene is dissolved in N, in the dinethylformamide, measures its ultraviolet-visible absorption spectroscopy, as shown in Figure 3, its absorption bands is wide, and maximum absorption wavelength is at the 377nm place.
Embodiment 4
4'-(4''-bromobenzene benzyloxy)-4-nitro diphenyl ethylene radiation of visible light produces creating singlet oxygen by using down
In the long horminess glass tube of 25cm, adding concentration is 1 * 10 -5The 4'-of mol/L (4''-bromobenzene benzyloxy)-4-nitro diphenyl ethylene acetonitrile solution 15ml and concentration are 2 of 1mol/L; 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'-(3'', 5''-dibrominated benzyloxy)-4-nitro diphenyl ethylene produces creating singlet oxygen by using under radiation of visible light
In the long horminess glass tube of 25cm, adding concentration is 1 * 10 -54'-(the 3'' of mol/L; 5''-dibrominated benzyloxy)-4-nitro diphenyl ethylene acetonitrile solution 15ml and concentration are 2 of 1mol/L; 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'-(2'', 3'', 4'', 5'', the inferior methoxyl group of 6''-phenyl-pentabromide)-4-nitro diphenyl ethylene produces creating singlet oxygen by using under radiation of visible light
In the long horminess glass tube of 25cm, adding concentration is 1 * 10 -5The 4'-of mol/L (2'', 3'', 4''; 5''; The inferior methoxyl group of 6''-phenyl-pentabromide)-and 4-nitro diphenyl ethylene acetonitrile solution 15ml and concentration are 2 of 1mol/L, 3-dihydropyrane acetonitrile solution 5ml is 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 (4)

  1. Straight chain type contain bromine atoms to the nitro toluylene photosensitizers, 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 5Represent 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. 2. the described straight chain type of claim 1 contains the compound method to the nitro toluylene photosensitizers of bromine atoms, it is characterized in that:
    Synthesis step is following:
    The first step: benzyl bromine synthetic that contains bromine atoms
    The toluene and the N-bromo-succinimide (NBS) that contain bromine atoms be with mol ratio 1:1.1 ratio, and promptly the molar weight of N-bromo-succinimide is 1.1 times of molar weight that contain the toluene of bromine atoms, in the ground-in three-necked flask, mixes, and installs condensing works, at CCl 4In refluxed 48 hours, be cooled to room temperature, filter, filtrating is revolved dried, with benzene/cyclohexane recrystallization, must white crystal, subsequent use;
    Reaction equation:
    Figure 960746DEST_PATH_IMAGE004
    R in the molecular structural formula wherein 1, R 2, R 3, R 4, R 5Represent 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: straight chain type contains the synthesizing the nitro toluylene photosensitizers of bromine atoms
    4-hydroxyl-4'-nitro diphenyl ethylene is joined in the ground-in three-necked flask, then with the exsiccant acetone solution of 200-350 times of volume ratio, argon shield; The basic catalyst that adds mol ratio 1:2, promptly the molar weight of basic catalyst is 2 times of molar weight of 4-hydroxyl-4'-nitro diphenyl ethylene, normal-temperature reaction 10 minutes; Add the hexaoxacyclooctadecane-6 that mol ratio is 20:1-6 again, promptly 20 times of the molar weight of 4-hydroxyl-4'-nitro diphenyl ethylene hexaoxacyclooctadecane-6-6 molar weight that is, at last with the bromated benzyl bromine of the first step gained and 4-hydroxyl-4'-nitro diphenyl ethylene with mol ratio 2:1; The molar weight that promptly contains the bromobenzyl bromine is 2 times of 4-hydroxyl-4'-nitro diphenyl ethylene molar weight, joins in the ground-in three-necked flask room temperature reaction 24 hours; Reaction finishes to remove acetone under the decompression of back, dissolves again with trichloromethane, adds the deionized water extraction; Collected organic layer is used anhydrous magnesium sulfate drying; Remove by filter siccative, solution decompression is concentrated, with benzene and chloroform recrystallization 2 times; Obtain yellow solid, be the compound of claim 1.
  3. The described straight chain type of claim 2 contain bromine atoms in the nitro toluylene photosensitizers Preparation Method, described basic catalyst is sodium alkoxide, potassium alcoholate, sodium hydroxide, Pottasium Hydroxide, Anhydrous potassium carbonate etc. or its arbitrary proportion mixture.
  4. The described straight chain type of claim 1 contain bromine atoms to the nitro toluylene photosensitizers, its purposes is: as visible light according to the photosensitizers that produces creating singlet oxygen by using.
CN2011102932242A 2011-10-08 2011-10-08 Straight chain type para nitro toluylene photosencitizer containing bromine atoms, synthesis and application thereof Pending CN102516084A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN101838475A (en) * 2010-05-28 2010-09-22 重庆大学 P-nitryl diphenylethylene dye sensitizing agent containing bromine as well as synthesis and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN101838475A (en) * 2010-05-28 2010-09-22 重庆大学 P-nitryl diphenylethylene dye sensitizing agent containing bromine as well as synthesis and application thereof

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Application publication date: 20120627