CN105566199A - Conjugated aralkynyl carbazole compound - Google Patents

Conjugated aralkynyl carbazole compound Download PDF

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CN105566199A
CN105566199A CN201410538960.3A CN201410538960A CN105566199A CN 105566199 A CN105566199 A CN 105566199A CN 201410538960 A CN201410538960 A CN 201410538960A CN 105566199 A CN105566199 A CN 105566199A
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carbazole
sweet
conjugation
compound
smelling alkynyl
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CN105566199B (en
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王涛
赵宝东
刘吉强
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Beijing University of Chemical Technology
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Beijing University of Chemical Technology
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Abstract

The invention discloses a conjugated aralkynyl carbazole compound. The conjugated aralkynyl carbazole compound is characterized in that a benzene ring is the center of the compound and a basin-shaped molecule is formed by symmetric substitution of the position 1 and position 4 of the benzene ring with carbazole groups containing aralkynyl groups. The compound is prepared by subjecting halogenated ferrocenium salt to a nucleophilic substitution reaction and then carrying out a photolysis reaction; so the compound is simple to prepare. The conjugated aralkynyl carbazole compound has high fluorescence quantum yield and strong two-photon absorption performance and can be applied to two-photon absorption materials like two-photon fluorescence probe compounds and optical information recording mediums.

Description

One class conjugation sweet-smelling alkynyl carbazole compound
Technical field
The present invention relates to a class conjugation sweet-smelling alkynyl carbazole compound, be specifically related to a kind of centered by phenyl ring, conjugation sweet-smelling alkynyl carbazole, at the disubstituted asymmetric conjugate molecule in the Isosorbide-5-Nitrae position of phenyl ring, belongs to two-photon absorbing material technical field.
Background technology
Carbazole, as a kind of special heteroaromatic compound, has extremely important application at chemical industry and field of medicaments.Three aspects below this main attribution (J.Polym.Sci., PartA:Polym.Chem., 2008,46,5180-5193): (1) have planarity, etc. electro rigid structure; (2) at its C-1,8,3,6,2,7 and N-9 position can replace by other groups; (3) good hole transport ability.
Carbazole derivative, because its special optical physics feature, comprises good transferring charge, electroluminescent, heat and morphology stable, makes it have application prospect in fields such as electroluminescent organic material, unbodied organic light refraction material, dye-sensitized cells.
Aromatic hydrocarbons has the rigid structure of conjugacy, planarity, and acetylene union has transmission electronic, the bridge connector of prolongation conjugated system can be bridged in various structure, and both combine thus form the conjugation aryne derivative of abundant species.This compounds generally has larger conjugated system, and after being stimulated, system has Intramolecular electron transfer largely, so this analog derivative generally all has a wide range of applications in photoelectricity special material field.
Molecule with carbazole unit has good thermostability, special electrochemistry and photochemical activity, has been designed at present to be applied in the functional materialss such as nonlinear optical material, electroluminescent organic material, organic photovoltaic material, organic molecule wire.And diaryl acetylene structural unit has the rigid structure of line style, there is good electronic transmission performance, usually used as the bridge linkage group of large conjugated molecule.Diaryl acetylene compounds with carbazole unit has had the character of carbazole and conjugation aryl ethane and functional concurrently, and therefore, this quasi-molecule has become one of focus of development research novel photoelectric functional materials.
The polymkeric substance that ToshioMasuda group reports (Polymer., 2008,49,4494 – 4501) is prepared by sweet-smelling alkynyl substituted carbazole is potential is applied to electroluminescent, embedded photoluminescent material; Yang Yang reports (J.Org.Chem., 2009,74,383 – 395), and a kind of dendritic macromole containing sweet-smelling alkynyl substituted carbazole structure is applied to Organic Light Emitting Diode (OLED); 3 compounds connected by groups such as aryne of VandanaBhalla also reports (RSCAdv., 2013,3,14722-14730) azanyl substituted carbazole molecule are applied to OLEDs.But there is conjugation sweet-smelling alkynyl carbazole derivative and be applied to the report of two-photon absorbing material aspect or fewer.
three. summary of the invention
The object of the invention is to provide a kind of conjugation sweet-smelling alkynyl carbazole compound thing with two-Photon Absorption Properties, and this compounds has high single molecular fluorescence quantum yield and comparatively strong two-photon absorption cross section, and is comparatively easy to synthesis.
For achieving the above object, the technical solution used in the present invention is: a class conjugation sweet-smelling alkynyl carbazole compound, and it is characterized in that, it is centered by phenyl ring, and conjugation sweet-smelling alkynyl carbazole is at 1 and 4 disubstituted asymmetric conjugate molecules of phenyl ring, and its general formula is:
Wherein R 1, R 2, R 3, R 4be selected from by following structure by oneself:
Wherein R abe selected from by the following group formed by oneself: hydrogen, alkyl, alkoxyl group, alkynyl, aryl and heteroaryl; R bbe selected from by the following group formed by oneself: hydrogen, alkyl, thiazolinyl, allyl group, aryl and heteroaryl; R c, R d, R ebe selected from by the following group formed by oneself: hydrogen, alkyl, alkoxyl group, amino, thiazolinyl, alkynyl, aryl and heteroaryl.
The object of the present invention is to provide the preparation method of conjugation sweet-smelling alkynyl carbazole compound, its step comprises:
(1), before reaction heating start heating after first nitrogen bubble 0-60min, treat that temperature is raised to 60-100 DEG C and adds terminal arylalkyne again.Bromo carbazole, terminal alkyne compound, Pd (PPh 3) 2cl 2, CuI, PPh 3amount ratio is 1:1-3:0.001-0.05:0.05-0.10:0.00-0.10.Until bromo carbazole reacts completely, filter, filtrate pouring into pour in the aqueous solution of saturated ammonium chloride, with dichloromethane extraction and dry organic phase, column chromatography is purified and is obtained carbazole alkine compounds.
(2), under lucifuge condition, the luxuriant molysite of dichlorobenzene, carbazole alkyne derivatives and K 2cO 3adding in reaction flask, take DMF as solvent, reacting by heating to 60 DEG C.Be poured in large water gaging after reaction terminates, separate out yellow mercury oxide, lucifuge operation in process.Filter filter cake lucifuge are dried, column chromatography is purified;
(3), obtain luxuriant molysite and obtain final part product by above-mentioned by photodissociation.
Conjugation sweet-smelling alkynyl carbazole compound is the object of the present invention is to provide to be applied to two-photon absorbing material, as the application of the aspects such as two-photon fluorescence probe compound, optical data recording medium
The present invention compared with prior art has following characteristic:
1, conjugation sweet-smelling alkynyl carbazole compound of the present invention has comparatively strong two-photon absorption cross section and single molecular fluorescence quantum yield, and at 720nm place, the two photon absorption cross section of described compound 4 is 448.1GM, single molecular fluorescence quantum yield can reach 0.63
2, in the present invention, conjugation sweet-smelling alkynyl carbazole compound makes raw material with sweet-smelling alkynyl carbazole, the luxuriant molysite of santochlor, obtains part product by nucleophilic substitution reaction and photolysis.Compared with bibliographical information, synthetic method of the present invention is more simple, does not take high temperature, does not need metal catalyst; Raw material is easy to get, and cost is low.
four. accompanying drawing explanation
Accompanying drawing 1 is the compound of embodiment 1 acquisition 1hNMR schemes.
Accompanying drawing 2 is the compound of embodiment 2 acquisition 1hNMR schemes.
Accompanying drawing 3 is the compound of embodiment 3 acquisition 1hNMR schemes.
Accompanying drawing 4 is the compound of embodiment 4 acquisition 1hNMR schemes.
Accompanying drawing 5 is the two-photon fluorescence spectrum of the compound that the embodiment of the present invention 1 obtains.
Accompanying drawing 6 is the two photon absorption cross section of the compound of the embodiment of the present invention 1 ~ 4.
five. embodiment
embodiment 1: the synthesis of Isosorbide-5-Nitrae-two (9-(3-phenylacetylene carbazyl)) benzene.
(1) by carbazole (16.7g, 100mmol) be dissolved in the DMF of 100mL, mechanical stirring in the four-hole boiling flask of 500mL, with cryosel bath control temperature between-5 DEG C to-10 DEG C, add 100mL again and be dissolved with NBS (18.7g, DMF solution 105mmol), slowly drips, and continues stirring reaction and spends the night.Reaction solution is inclined and is added to the water vigorous stirring, filter and dry filter cake.Re-crystallizing in ethyl acetate, obtains 16.6g3-bromo carbazole, productive rate 67.6%.
(2) in the four-hole boiling flask of 500ml, add 3-bromine carbazole (10.0g, 40.6mmol), dissolved with 50mL triethylamine and 100mLDMF, then add Pd (PPh 3) 2cl 2(200mg, 0.28mmol), CuI (1.5g, 8.0mmol), PPh 3(3.14g, 12.0mmol).First logical nitrogen bubble 30min, is slowly heated to backflow, then adds phenylacetylene and continue logical nitrogen protection heated and stirred backflow 8h.By reacting liquid filtering desalination after reaction terminates, filtrate decompression revolves steaming, debris to be poured in the aqueous solution of saturated ammonium chloride with dichloromethane extraction and dry organic phase, filtrate being spin-dried for is obtained viscous brown thing by elimination solid, column chromatography purification (sherwood oil: ethyl acetate is 3:1) obtains white plates crystal 3-phenylacetylene carbazole, and productive rate is 74.6%.
(3) 3-is replaced bromine carbazole, the luxuriant molysite of santochlor, K 2cO 3be placed in 250mL there-necked flask, add 100mLDMF, temperature control 60 DEG C of lucifuge magnetic agitation reaction 6h.Be poured in large water gaging after reaction terminates, separate out yellow mercury oxide, lucifuge operation in process.Filter filter cake lucifuge are dried.Column chromatography carry out purification obtain yellow solid [( η 6-Isosorbide-5-Nitrae-two (9-(3-phenylacetylene carbazyl)) phenyl)-iron-( η 5-cyclopentadienyl)] hexafluorophosphate, productive rate is 62.1%.
(4): get 1g [( η 6-Isosorbide-5-Nitrae-two (9-(3-phenylacetylene carbazyl)) phenyl)-iron-( η 5-cyclopentadienyl)] hexafluorophosphate is dissolved in 20mLDMF solution and fully dissolves, and under being positioned over high voltage mercury lamp, liquid level of solution is apart from mercury lamp condensation sleeve pipe 110mm, and magnetic agitation, illumination is until fragrant luxuriant iron cpd point disappears.After photodissociation completely, filter and obtain filter cake, column chromatography purifies (sherwood oil: ethyl acetate=5:1).Organic phase pours in water, and have a small amount of solid to separate out, filtration is dried, column chromatography is purified (sherwood oil: ethyl acetate=5:1), merges purification gained Isosorbide-5-Nitrae-two (9-(3-phenylacetylene carbazyl)) benzene, faint yellow solid, productive rate 81.9%, fusing point is greater than 260 DEG C.
1HNMR(400MHz,DMSO- d 6 )δ8.59(s,2H),8.39(t, J=10.0Hz,2H),7.98(d, J=8.9Hz,4H),7.77–7.52(m,12H),7.51–7.36(m,8H)； 13CNMR(100MHz,CDCl 3)δ141.18,140.32,136.54,131.54,129.78,128.45,128.39,127.97,126.68,124.12,123.75,123.70,123.19,120.87,120.67,114.98,109.98,109.84,90.48,88.10；IR(KBr;?(cm -1)):2215.5(ν,C≡C),1185.5(ν,C-N)，MS:[M] +608.86。
The compound molecule formula that the present embodiment obtains is,
embodiment 2:the synthesis of Isosorbide-5-Nitrae-two (9-(3-(4-p-methoxy-phenyl) ethynyl) carbazyl) benzene.
Synthetic method is similar to Example 1, only need change the phenylacetylene in step (2) in embodiment 1 into 4-Methoxy-phenylacetylene according to acquisition compound.
Productive rate 84.5%, 1hNMR (400MHz, DMSO- d 6 ) δ 8.55 (s, 2H), 8.39 (d, j=7.8Hz, 2H), 7.98 (s, 4H), 7.73 – 7.60 (m, 6H), 7.60 – 7.50 (m, 6H), 7.40 (t, j=7.4Hz, 2H), 7.03 (d, j=8.8Hz, 4H), 3.82 (s, 6H), 13cNMR (100MHz, CDCl 3) δ 159.44,141.16,140.15,136.54,132.96,129.66,128.42,126.61; 123.89,123.67,123.21,120.80,120.65,115.86,115.32; 114.04,109.96,109.80,89.03,87.96,55.33, IR (KBr; (cm -1)): 2225.5 (ν, C ≡ C), 1187.9 (ν, C-N).
The molecular formula obtained is,
embodiment 3: the synthesis of Isosorbide-5-Nitrae-two (9-(3,6-bis-(phenylacetylene base)) carbazyl) benzene.
Synthetic method and embodiment 1similar, only need to change embodiment 1step (1) is following steps:
(1) carbazole (17.6g, 100mmol) is dissolved in the DMF of 150mL, mechanical stirring in the four-hole boiling flask of 500mL, then drips the DMF solution that 150mL is dissolved with NBS (35.6g, 200mmol), add complete in batches.Cryosel bath hierarchy of control temperature, below 0 DEG C, continues stirring reaction again and spends the night after dropwising.Reaction solution is inclined and is added to the water vigorous stirring, filter and dry filter cake.The two bromine carbazole of 3,6-is obtained, productive rate 80.1% by re-crystallizing in ethyl acetate.
And embodiment (2) 1in (2-4) similar, only need change and embodiment 13-bromo carbazole in step (2).
Productive rate 86.2%, 1hNMR (400MHz, DMSO- d 6 ) δ 8.41 (s, 4H), 7.89 (s, 4H), 7.71 (dd, j=8.5,1.3Hz, 4H), 7.64 (d, j=6.5Hz, 8H), 7.56 (d, j=8.5Hz, 4H), 7.47 – 7.35 (m, 12H), 13cNMR (100MHz, CDCl 3) δ 140.67,131.56,130.24,129.05,128.53,128.40,128.07,124.26,123.61,123.28,115.63,110.04,90.17, IR (KBr; (cm -1)): 2203.2 (ν, C ≡ C), 1172.3 (ν, C-N).
The molecular formula obtained is,
embodiment 4: the synthesis of Isosorbide-5-Nitrae-two (9-(3,6-bis-(((4-methoxyl group) phenyl) ethynyl)) carbazyl) benzene.
Synthetic method and embodiment 3similar, only need according to acquisition compound by embodiment 3phenylacetylene in middle step (2) changes 4-Methoxy-phenylacetylene into.
Productive rate is 85.3%, 1hNMR (400MHz, DMSO- d 6 ) δ 8.61 (s, 4H), 8.01 (s, 4H), 7.68 (m, 8H), 7.56 (d, j=8.6Hz, 8H), 7.03 (d, j=8.7Hz, 8H), 3.83 (s, 12H), 13cNMR (100MHz, CDCl 3) δ 158.47,139.43,135.35,131.96,129.03,127.41,122.97,122.25,114.86,114.71,113.03,108.95,103.97,87.78,87.22,54.31, IR (KBr; (cm -1)): 2203.1 (ν, C ≡ C), 1169.2 (ν, C-N).
The molecular formula obtained is,
embodiment 5: the two-photon absorption property detection of conjugation sweet-smelling alkynyl carbazole compound
Whether have two-photon absorption at a kind of material of numerous detection or measure in the method for its two photon absorption cross section, two-photon fluorescence excitation (TPEF) method is that wherein one the most simply detects and measuring method.
The test condition of sample is: Tsunami-Spitfire-OPA-800C laser apparatus, and wavelength is that 720-880nm is adjustable, and repetition is 80MHz, and pulse width Wei≤100fs, experiment laser intensity is 8.2GW/cm 2, spot diameter is 2mm.
This patent adopts rhodamine B as reference substance, makes 1 × 10 -4the methanol solution of mol/L, and for embodiment 1with 2, make 1 × 10 -3the tetrahydrofuran solution of mol/L; For embodiment 3with 4, make 1 × 10 -4the tetrahydrofuran solution of mol/L, table 1 is obtained experimental data.
The linear optics of table 1 conjugation sweet-smelling alkynyl carbazole derivative and two-photon absorption character

Claims (6)

1. a class conjugation sweet-smelling alkynyl carbazole compound, it is characterized in that, it is centered by phenyl ring, and conjugation sweet-smelling alkynyl carbazole is at 1 and 4 disubstituted asymmetric conjugate molecules of phenyl ring, and its general formula is:
Wherein R 1, R 2, R 3, R 4be selected from following structure by oneself:
。
2. conjugation sweet-smelling alkynyl carbazole compound according to claim 1, R abe selected from by the following group formed by oneself: hydrogen, alkyl, alkoxyl group, alkynyl, aryl and heteroaryl; R bbe selected from by the following group formed by oneself: hydrogen, alkyl, thiazolinyl, allyl group, aryl and heteroaryl; R c, R d, R ebe selected from by the following group formed by oneself: hydrogen, alkyl, alkoxyl group, amino, thiazolinyl, alkynyl, aryl and heteroaryl.
3. the preparation method of conjugation sweet-smelling alkynyl carbazole compound according to claim 1, its step comprises:
(1), under nitrogen protection, bromo carbazole, terminal alkyne compound, Pd (PPh 3) 2cl 2, CuI, PPh 3, TEA and DMF join in reaction flask in batches, be heated to backflow, heating is until bromo carbazole reacts completely, and filtration, filtrate pouring into are poured in the aqueous solution of saturated ammonium chloride, with dichloromethane extraction and dry organic phase, column chromatography is purified and is obtained carbazole alkine compounds;
(2), under lucifuge condition, the luxuriant molysite of dichlorobenzene, carbazole alkyne derivatives and K 2cO 3adding in reaction flask, take DMF as solvent, reacting by heating to 60 DEG C; Be poured in large water gaging after reaction terminates, separate out yellow mercury oxide, lucifuge operation in process; Filter filter cake lucifuge are dried, column chromatography is purified;
(3), obtain luxuriant molysite and obtain final part product by above-mentioned by photodissociation.
4. the preparation method of conjugation sweet-smelling alkynyl carbazole compound according to claim 3, is characterized in that: in described step (1), bromo carbazole, terminal alkyne compound, Pd (PPh 3) 2cl 2, CuI amount ratio be 1mmol:1-3mmol:0.001-0.05mmol:0.05-0.10mmol.
5. the preparation method of conjugation sweet-smelling alkynyl carbazole compound according to claim 3, it is characterized in that: in described step (1), in order to contain side reaction, heating is started after first nitrogen bubble 0-60min before reaction heating, treat that temperature is raised to 60-100 DEG C and adds terminal arylalkyne again, continue logical nitrogen until thin-layer chromatography detection bromo carbazole raw material reaction is complete.
6. conjugation sweet-smelling alkynyl carbazole compound according to claim 1 is applied to two-photon absorbing material, as the application of the aspects such as two-photon fluorescence probe compound, optical data recording medium.
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CN109438155A (en) * 2018-11-20 2019-03-08 安庆北化大科技园有限公司 It is conjugated alkynyl anthracene derivative, preparation method and applications
CN115340578A (en) * 2021-05-14 2022-11-15 安庆北化大科技园有限公司 Novel arylamine molysite photoinitiator and preparation method and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018120973A1 (en) * 2016-12-30 2018-07-05 广东阿格蕾雅光电材料有限公司 Host material applied to organic light-emitting diode
CN109438155A (en) * 2018-11-20 2019-03-08 安庆北化大科技园有限公司 It is conjugated alkynyl anthracene derivative, preparation method and applications
CN115340578A (en) * 2021-05-14 2022-11-15 安庆北化大科技园有限公司 Novel arylamine molysite photoinitiator and preparation method and application thereof

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