CN101768112B - Two-photon induced luminous compound with symmetrical both ends and synthesis method and purposes thereof - Google Patents
Two-photon induced luminous compound with symmetrical both ends and synthesis method and purposes thereof Download PDFInfo
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Abstract
The invention relates to the technical fields of luminous material, two-photon absorption material, optical storage and the like, in particular to two-photon induced luminous compound with symmetrical both ends and a synthesis method and purposes thereof. Raw material sodium methoxide is added into N, N-DMF solvent which is dissolved with phosphate reagent to be uniformly stirred, and then aldehyde is added in to react; the reaction solution is poured into water and filtered; the prepared hot ethanol for residue is filtered; and chromatographic separation is carried out to the rest solid, and the two-photon induced luminous compound with symmetrical both ends is prepared. After being doped into an epoxy resin solid matrix, the two-photon induced luminous compound with both ends symmetrical prepares strong two-photon induced luminous solid material which can be used for fluorescent probes or fluorescence imaging material. The two-photon induced luminous compound with symmetrical both ends of the invention is a type of two-photon induced luminous 1, 2, 2 and 4-tetramethyl-dihydro-quinoline compound with both ends symmetrical, and the structure of the two-photon induced luminous compound is shown as the accompanying drawing.
Description
Technical field
The present invention relates to luminescent material, technical fields such as two-photon absorbing material and optical storage, particularly symmetric photon induced luminous compound in two ends and preparation method and use thereof.
Background technology
Luminescent material is meant the material that after receiving various energy excitations, can send visible light.This type material has been widely used in high-tech areas such as FPD, laser, illumination optical, probe biomolecule.In the today that gets into the information age, can satisfy various information and show that the luminescent material development of demand is particularly rapid.Luminous organic material mainly is made up of organism, has to be easy to purify through structural modification adjustment performance, easily and advantage such as with low cost, and has the film forming meliority of easy big area.Photon induced luminous material has crucial application in fields such as two-photon fluorescence imaging and microscopy, three-dimensional information storage, optical dynamic therapy, non-linear up-conversion and two-photon fluorescence transmitters.
Most representative about the photon induced luminous field of organic cpds at present is Prasad and Marder research group, and the most molecule of research also all concentrates on molecule (He, the G.S of substituted phenylethylene type; Bhawalkar, J.D; Zhao, C.F; Park, C.K; Prasad, P.N.Opt.Lett.1995,20,2393).Two photon absorption cross section character δ and fluorescence quantum yield Φ are two importances weighing the photon induced luminous compound performance.And their product Φ δ to be photon induced fluorescent emission cross section be weighs the primary index of photon induced luminous compound performance.Previous studies shows that under the identical conjugate length of the molecule condition identical with same test concentration etc., the two photon absorption cross section character δ of symmetric form molecule obviously is superior to unsymmetric molecule (Albota, M; Beljonne, D; Bredas, J-L; Ehrlich, J.E; Fu, J-Y; Heikal, A.A; Hess, S.E; Kogej, T; Levin, M.D; Marder, S.R; McCord-Maughon, D; Perry, J.W; Rockel, H; Rumi, M; Subramaniam, G; Webb, W.W; Wu, X-L.Xu, C.Science.1998,281,1653).In addition, strong electron-donating group, such as the adding of amido, the conjugated system with increasing compound helps increasing two photon absorption cross section δ.Yet the rotation meeting of amido is in the reduction that causes compound light-emitting efficient in varying degrees (Entwistle C.D., Marder, T.B., Chem.Mater., 2004,16,4574).End through with the N atom is fixed into ring, helps to reduce the non-radiation deactivation rate that the amido rotation causes, increases the fluorescence quantum yield Φ of compound, correspondingly increases Φ δ value.Photon induced luminous quantum yield of the present invention (quantum yield of embodiment 1 is 0.83) is wanted high many (Tian Yupeng, Wu Jieying, Hao Fuying, Yang Jiaxiang, Zhang Shengyi than the compound (PDASB, quantum yield are 0.112) of Tian Yupeng group report.Chinese invention patent, application number 03112764.9).
Summary of the invention
One of the object of the invention is to provide one type of symmetric photon induced luminous compound in two ends.
Two of the object of the invention is to provide the compound method of one type of symmetric photon induced luminous compound in two ends.
Three of the object of the invention is to provide the purposes of one type of symmetric photon induced luminous compound in two ends.
The symmetric photon induced luminous compound in two ends of the present invention is the strong two-photon induced luminous compound of the symmetric toluylene skeleton in two ends; It is one type and has 1,2,2 of two ends symmetric strong two-photon induced luminescence characteristic; 4-tetramethyl-compound in category of dihydro quinolines has following structure:
Wherein: R is H, methyl, ethyl, allyl group, phenyl, tolyl, itrile group, a kind of in the methoxy or ethoxy.
The compound method of the symmetric photon induced luminous compound in two ends of the present invention:
1). with raw material according to aldehyde: SULPHOSUCCINIC ACID ESTER reagent: sodium methylate=(2～2.5): (0.9～1): the mol ratio of (5.5～6.5); Earlier sodium methylate is joined the N that is dissolved with SULPHOSUCCINIC ACID ESTER reagent; In the dinethylformamide solvent; Stir (being generally 20～40 minutes), added aldehyde reaction again 1.5～3 hours;
2). in the reaction solution impouring water that step 1) is obtained, filter; The filter residue that obtains filters with the ethanol of heat below the boiling point; Remaining solid with silica gel column chromatography separate the symmetric photon induced luminous compound in two ends.
Described aldehyde is 1,2,2,4-tetramethyl--1,2-dihydro-6-formyl radical quinoline.
Described SULPHOSUCCINIC ACID ESTER reagent be 2,5 substituted 1,4-two (diethoxy phosphoryl) methyl-benzene.
Described 2,5 substituted 1, the substituting group in 4-two (diethoxy phosphoryl) methyl-benzene is selected from H, methyl, ethyl, allyl group, phenyl, tolyl, itrile group, a kind of in the methoxy or ethoxy.
The symmetric photon induced luminous compound in two ends of the present invention in being doped to the epoxy resin solid substrate after, can prepare the solid material of strong two-photon induced luminescence.
Adopt epoxy resin to prepare and be doped with 1 of the symmetric photon induced luminous characteristic in two ends that has of the present invention; 2; 2, the solid two-photon luminescent material of 4-tetramethyl-compound in category of dihydro quinolines, embrittlement takes place in gel glass easily in the sol-gel method in heat treatment process to overcome; The material mechanical performance and the snappiness that make are very poor, and the porousness of gel glass also is prone to cause the shortcoming of bigger scattering loss.Be doped with 1 of the symmetric photon induced luminous characteristic in two ends that has of the present invention; 2,2, the solid material transparency of the strong two-photon induced luminescence of 4-tetramethyl-compound in category of dihydro quinolines is high; Have the strong two-photon luminescent properties, can be used for fluorescent probe or fluorescence imaging material and use.
Get the epoxy resin of 4～4.5ml, 2～3ml polyamine (EP3302UCL-B) is in container, and stirring mixes it under the room temperature, and adding 40～60ul concentration again is 1 * 10
-3Mol have 1,2,2 of a symmetric photon induced luminous characteristic in two ends, THF (THF) solution of 4-tetramethyl-compound in category of dihydro quinolines is stirred to mixture homogeneous, transparent; This mixture is moved in the flat quartz container; Place in the vacuum drier, vacuumize under the room temperature, begin heating after about 2～4 hours to remove the bubble in the mixture; Make it 80～100 ℃ of curing, obtain homogeneous, transparent photon induced luminous solid material after 8～10 hours.This photon induced luminous solid material can be used for fluorescent probe or the fluorescence imaging material uses.
Described epoxy resin is bisphenol-A neutral (referring to that acid-basicity is neutral) epoxy resin (EP3302UCL-A).
The two-photon absorption performance that the present invention is based on toluylene has been invented the strong two-photon induced luminous compound with two ends symplex structure that N one end becomes to encircle, and it is doped in the solid substrate, obtains adulterated solid luminescent material.This adulterating method is simple, and can overcome the generation embrittlement easily in heat treatment process of conventional gel glass, and the material mechanical performance and the snappiness that make are very poor, and the porousness of gel glass also is prone to cause the shortcoming of bigger scattering loss.It is high to obtain solid doped material transparency with this method, has the strong two-photon luminescent properties.
Strong two-photon inducing compounds of the present invention and solid doped material have bigger two photon absorption cross section, have potential in fields such as two-photon fluorescence imaging and microscopy and light amplitude limits and use.
Description of drawings
Fig. 1. the embodiment of the invention 1 synthetic 1,4-two (E)-(1 ', 2 '-dihydro-1 ', 2 ', 2 ', 4 '-tetramethyl-quinolyl-6 ') vinyl-2, the 5-dimethoxy benzene is doped to the photo of the solid material of gained in the solid substrate.
Fig. 2. the embodiment of the invention 3 synthetic 1,4-two (E)-(1 ', 2 '-dihydro-1 ', 2 ', 2 ', 4 '-tetramethyl-quinolyl-6 ') vinyl-2, the 5-dimethyl benzene is doped to the photon induced luminous photo of the solid material of gained in the solid substrate.
Embodiment
Embodiment 1
Restrain (7.2mmol) 2 to being dissolved with 2.96,5-dimethoxy-1,50 milliliters of 4-two (diethoxy phosphoryl) methyl-benzene are heavily steamed N, add 2.38 gram (44.0mmol) sodium methylates in dinethylformamide (DMF) solution; Stir after 20 minutes, add 3.44 gram (16.0mmol) 1,2; 2,4-tetramethyl--1,2-dihydro-6-formyl radical quinoline; Reaction is 1.5 hours under the room temperature, afterwards with in the product solution impouring water, filters.Filter residue filters with the ethanol of heat below the boiling point, and the separation of recycle silicon glue column chromatography (eluant: methylene dichloride/hexanaphthene=100/20, v/v), rotary evaporation removes and desolvates, and vacuum-drying obtains pure article.The present invention is with 1,2,2,4-tetramethyl--1; 2-dihydro-6-formyl radical quinoline and 2,5-dimethoxy-1,4-two (diethoxy phosphoryl) methyl-benzene is raw material, 1 of the symmetric photon induced luminous characteristic of processing in two ends; 2,2,4-tetramethyl-compound in category of dihydro quinolines.M.P.230～233℃.
1HNMR(300MHz，CDCl3)：δ7.30-7.14(m，10H)，6.51(d，2H，J＝7.7Hz)，5.37(s，2H)，3.86(s，6H)，2.76(s，6H)，1.96(s，6H)，1.32(s，12H).MALDI-TOF-MS：M?560.3.Anal.Calcd.(％)For?C
38H
44N
2O
2：C?81.39，H?7.91，N?5.00；found：C?81.29，H?7.90，N?5.00。
Single two-photon performance test data of the compound 1 that embodiment 1 obtains is as shown in table 1.
To being dissolved with 2.60 gram (7.4mmol) 1,50 milliliters of 4-two (diethoxy phosphoryl) methyl-benzene are heavily steamed adding 2.51 gram (46.4mmol) sodium methylates in the DMF solution, stir after 25 minutes; Add 3.70 gram (17.2mmol) 1,2,2; 4-tetramethyl--1,2-dihydro-6-formyl radical quinoline, reaction is 3 hours under the room temperature; With in the product solution impouring water, filter afterwards.Filter residue filters with the ethanol of heat below the boiling point, and the separation of recycle silicon glue column chromatography (eluant: methylene dichloride/hexanaphthene=100/20, v/v), rotary evaporation removes and desolvates, and vacuum-drying obtains pure article.The present invention is with 1,2,2,4-tetramethyl--1, and 2-dihydro-6-formyl radical quinoline and 1,4-two (diethoxy phosphoryl) methyl-benzene is raw material, 1,2,2 of the symmetric photon induced luminous characteristic of processing in two ends, 4-tetramethyl-compound in category of dihydro quinolines.
1HNMR(300MHz，CDCl3)：δ7.51(s，4H)，7.33-6.89(m，8H)，6.53(d，2H，J＝8.6Hz)，5.45(s，2H)，2.84(s，6H)，2.00(s，6H)，1.29(s，12H).MALDI-TOF-MS：M?500.4。Anal.Calcd.(％)for?C
36H
40N
2：C?86.35，H?8.05，N?5.59；found：C?86.11，H?8.03，N?5.60。
Single two-photon performance test data of the compound 2 that embodiment 2 obtains is as shown in table 1.
Restrain (7.8mmol) 2 to being dissolved with 2.95,5-dimethyl--1,50 milliliters of 4-two (diethoxy phosphoryl) methyl-benzene are heavily steamed adding 2.72 gram (50.4mmol) sodium methylates in the DMF solution; Stir after 30 minutes, add 4.13 gram (19.2mmol) 1,2; 2,4-tetramethyl--1,2-dihydro-6-formyl radical quinoline; Reaction is 2.0 hours under the room temperature, afterwards with in the product solution impouring water, filters.The filter residue filter residue filters with the ethanol of heat below the boiling point, and the separation of recycle silicon glue column chromatography (eluant: methylene dichloride/hexanaphthene=100/20, v/v), rotary evaporation removes and desolvates, and vacuum-drying obtains pure article.The present invention is with 1,2,2,4-tetramethyl--1; 2-dihydro-6-formyl radical quinoline and 2,5-dimethyl--1,4-two (diethoxy phosphoryl) methyl-benzene is raw material, 1 of the symmetric photon induced luminous characteristic of processing in two ends; 2,2,4-tetramethyl-compound in category of dihydro quinolines.
1HNMR(300MHz，CDCl3)：δ7.28-6.54(m，12H)，5.40(s，2H)，2.80(s，6H)，2.35(s，6H)，2.00(s，6H)，1.31(s，12H).MALDI-TOF-MS：M?528.3。Anal.Calcd.(％)for?C
38H
44N
2：C?86.31，H?8.39，N?5.30；found：C?86.10，H?8.38，N?5.32。
Embodiment 4
Restrain (7.5mmol) 2 to being dissolved with 3.23,5-diallyl-1,50 milliliters of 4-two (diethoxy phosphoryl) methyl-benzene are heavily steamed adding 2.59 gram (48.0mmol) sodium methylates in the DMF solution; Stir after 40 minutes, add 3.79 gram (17.6mmol) 1,2; 2,4-tetramethyl--1,2-dihydro-6-formyl radical quinoline; Reaction is 2.5 hours under the room temperature, afterwards with in the product solution impouring water, filters.The filter residue filter residue filters with the ethanol of heat below the boiling point, and the separation of recycle silicon glue column chromatography (eluant: methylene dichloride/hexanaphthene=100/20, v/v), rotary evaporation removes and desolvates, and vacuum-drying obtains pure article.The present invention is with 1,2,2,4-tetramethyl-1; 2-dihydro-6-formyl radical quinoline and 2,5-diallyl-1,4-two (diethoxy phosphoryl) methyl-benzene is raw material, 1 of the symmetric photon induced luminous characteristic of processing in two ends; 2,2,4-tetramethyl-compound in category of dihydro quinolines.
1HNMR(300MHz，CDCl3)：δ7.29-6.30(m，14H)，5.39(s，2H)，4.78-4.72(m，4H)，3.20(d，4H，J＝7.9Hz)，2.81(s，6H)，1.99(s，6H)，1.32(s，12H).MALDI-TOF-MS：M?580.38。Anal.Calcd.(％)for?C
42H
48N
2：C?86.85，H?8.33，N?4.82；found：C?86.70，H?8.31，N?4.82。
Embodiment 5
Restrain (8.0mmol) 2 to being dissolved with 4.01,5-phenylbenzene-1,50 milliliters of 4-two (diethoxy phosphoryl) methyl-benzene are heavily steamed adding 2.81 gram (52.0mmol) sodium methylates in the DMF solution; Stir after 25 minutes, add 4.31 gram (2.0mmol) 1,2; 2,4-tetramethyl--1,2-dihydro-6-formyl radical quinoline; Reaction is 1.5 hours under the room temperature, afterwards with in the product solution impouring water, filters.The filter residue filter residue filters with the ethanol of heat below the boiling point, and the separation of recycle silicon glue column chromatography (eluant: methylene dichloride/hexanaphthene=100/20, v/v), rotary evaporation removes and desolvates, and vacuum-drying obtains pure article.The present invention is with 1,2,2,4-tetramethyl--1; 2-dihydro-6-formyl radical quinoline and 2,5-phenylbenzene-1,4-two (diethoxy phosphoryl) methyl-benzene is raw material, 1 of the symmetric photon induced luminous characteristic of processing in two ends; 2,2,4-tetramethyl-compound in category of dihydro quinolines.
1HNMR(300MHz，CDCl3)：δ7.31-6.52(m，22H)，5.41(s，2H)，2.82(s，6H)，2.01(s，6H)，1.29(s，12H).MALDI-TOF-MS：M652.4。Anal.Calcd.(％)for?C
48H
48N
2：C?88.30，H?7.41，N?4.29；found：C?88.01，H?7.39，N?4.28。
Embodiment 6
Get epoxy resin (EP3302UCL-A) in 4 milliliters of bisphenol-As, 2 milliliters of polyamine (EP3302UCL-B) are in weighing bottle, and stirring mixes it under the room temperature, and adding 40 microlitre concentration again is 1 * 10
-31 of the embodiment 1 of mol, 4-two (E)-(1 ', 2 '-dihydro-1 ', 2 ', 2 ', 4 '-tetramethyl-quinolyl-6 ') vinyl-2, the tetrahydrofuran solution of 5-dimethoxy benzene is stirred to mixture homogeneous, transparent.This mixture is moved in the flat quartz container; Place in the vacuum drier, vacuumize under the room temperature, begin heating after about 2 hours to remove the bubble in the mixture; Make it 80 ℃ of curing, obtain the solid material of homogeneous, transparent strong two-photon induced luminescence after 10 hours.The solid material of this strong two-photon induced luminescence can be used for fluorescent probe or the fluorescence imaging material uses.The photo of the solid material of the strong two-photon induced luminescence of gained is as shown in Figure 1.
Embodiment 7
Get epoxy resin (EP3302UCL-A) in 4.5 milliliters of bisphenol-As, 3 milliliters of polyamine (EP3302UCL-B) are in weighing bottle, and stirring mixes it under the room temperature, and adding 60 microlitre concentration again is 1 * 10
-3Among the embodiment 3 of mol 1 of gained, 4-two (E)-(1 ', 2 '-dihydro-1 ', 2 ', 2 ', 4 '-tetramethyl-quinolyl-6 ') vinyl-2, the tetrahydrofuran solution of 5-dimethyl benzene is stirred to mixture homogeneous, transparent.This mixture is moved in the flat quartz container; Place in the vacuum drier, vacuumize under the room temperature, begin heating after about 4 hours to remove the bubble in the mixture; Make it 100 ℃ of curing, obtain the solid material of homogeneous, transparent strong two-photon induced luminescence after 8 hours.The solid material of this strong two-photon induced luminescence can be used for fluorescent probe or the fluorescence imaging material uses.The photon induced luminous photo of the solid material of the strong two-photon induced luminescence of gained is as shown in Figure 2.
Table 1:
| λ OPA (nm) | ?λ OPF?(nm) | Φ | δ a (GM) | |
| Compound 1 | 429 | 492 | 0.83 | 1160 |
| Compound 2 | 414 | 477 | 0.78 | 570 |
Annotate: λ
OPA: the maximum linear absorbing wavelength; λ
FPA: maximum emission wavelength; Φ: fluorescence quantum yield; δ
a: for two photon absorption cross section δ at the observed value at excitation wavelength 705nm place (with the δ of resorcinolphthalein at excitation wavelength 720nm place
TPA=30GM (1GM=1 * 10
-50Centimetre
4Second photon
-1) be the calculated value of reference.
Claims (6)
1. symmetric photon induced luminous compound in two ends, it is one type and has 1,2,2 of the symmetric photon induced luminous characteristic in two ends, and 4-tetramethyl-compound in category of dihydro quinolines is characterized in that, and this photon induced luminous compound has following structure:
Wherein: R is H, methyl, ethyl, allyl group, phenyl, tolyl, itrile group, a kind of in the methoxy or ethoxy.
2. the compound method of the symmetric photon induced luminous compound in two ends according to claim 1:
1). with raw material according to aldehyde: SULPHOSUCCINIC ACID ESTER reagent: the sodium methylate mol ratio is 2～2.5: 0.9～1: 5.5～6.5, earlier sodium methylate is joined the N that is dissolved with SULPHOSUCCINIC ACID ESTER reagent, in the dinethylformamide solvent, stir, added aldehyde reaction again 1.5～3 hours;
2). in the reaction solution impouring water that step 1) is obtained, filter; The filter residue that obtains filters with the ethanol of heat below the boiling point; Remaining solid with silica gel column chromatography separate the symmetric photon induced luminous compound in two ends;
Described aldehyde is 1,2,2,4-tetramethyl--1,2-dihydro-6-formyl radical quinoline;
Described SULPHOSUCCINIC ACID ESTER reagent be 2,5 substituted 1,4-two (diethoxy phosphoryl) methyl-benzene;
Described 2,5 substituted 1, the substituting group in 4-two (diethoxy phosphoryl) methyl-benzene is selected from H, methyl, ethyl, allyl group, phenyl, tolyl, itrile group, a kind of in the methoxy or ethoxy.
3. the purposes of the symmetric photon induced luminous compound in two ends according to claim 1; It is characterized in that: the symmetric photon induced luminous compound in described two ends in being doped to the epoxy resin solid substrate after, prepare photon induced luminous solid material.
4. purposes according to claim 3 is characterized in that: get the epoxy resin of 4～4.5ml, 2～3ml polyamine is in container, and stirring mixes it under the room temperature, and adding 40～60ul concentration again is 1 * 10
-3The tetrahydrofuran solution of the symmetric photon induced luminous compound in two ends of mol is stirred to mixture homogeneous, transparent; This mixture is moved in the flat quartz container; Place in the vacuum drier; Vacuumize under the room temperature to remove the bubble in the mixture, begin heating after 2～4 hours, make it after 80～100 ℃ of curing, obtain homogeneous, transparent photon induced luminous solid material.
5. according to claim 3 or 4 described purposes, it is characterized in that: described photon induced luminous solid material is used for fluorescent probe or the fluorescence imaging material uses.
6. according to claim 3 or 4 described purposes, it is characterized in that: described epoxy resin is epoxy resin in the bisphenol-A.
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| Martina Hauck等.Phenothiazine Cruciforms: Synthesis and Metallochromic Properties.《J. Org. Chem》.2007,第72卷第6714-6725页. * |
| 黄池宝等.2 ,5-二氰基-1 ,4-二(3′,4′,5′- 三甲氧基苯乙烯基) 苯的合成和非线性光学性质.《化学与生物工程》.2007,第24卷(第4期),第33-36页. |
| 黄池宝等.2,5-二氰基-1,4-二(3′,4′,5′- 三甲氧基苯乙烯基) 苯的合成和非线性光学性质.《化学与生物工程》.2007,第24卷(第4期),第33-36页. * |
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