CN110668975B - Dehydroabietic acid triarylamine D-pi-A type compound with benzene derivative as pi bridge and synthesis method thereof - Google Patents
Dehydroabietic acid triarylamine D-pi-A type compound with benzene derivative as pi bridge and synthesis method thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
- 229940118781 dehydroabietic acid Drugs 0.000 title claims abstract description 42
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 title claims abstract description 34
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000001308 synthesis method Methods 0.000 title abstract description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 27
- -1 dehydroabietic acid triarylamine compound Chemical class 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 238000005859 coupling reaction Methods 0.000 claims abstract description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 6
- 239000011259 mixed solution Substances 0.000 claims abstract description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000001555 benzenes Chemical class 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 abstract description 8
- 238000000862 absorption spectrum Methods 0.000 abstract description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical group C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241000234314 Zingiber Species 0.000 description 2
- 235000006886 Zingiber officinale Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000008397 ginger Nutrition 0.000 description 2
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 125000006617 triphenylamine group Chemical group 0.000 description 2
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- YBXGUHGVNUFFJU-UHFFFAOYSA-N 4-bromo-3-methylbenzaldehyde Chemical compound CC1=CC(C=O)=CC=C1Br YBXGUHGVNUFFJU-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- YDBQJGWNFSPUNX-UHFFFAOYSA-N [O-][N+](=O)BrC#N Chemical compound [O-][N+](=O)BrC#N YDBQJGWNFSPUNX-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical group O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention relates to a D-pi-A type compound which takes dehydroabietic acid triarylamine compound as an electron supply group (D), benzene and derivatives thereof are pi bridges, cyanoacetic acid is taken as an electron-withdrawing group (A) and a synthesis method thereof
Adding Pd catalyst and carbonate, carrying out C-C coupling reaction in a mixed solution of organic solvent and water to obtain a dehydroabietic acid triarylamine benzaldehyde compound (III), and reacting with cyanoacetic acid to obtain a dehydroabietic acid triarylamine D-pi-A type compound (IV). Compared with the dehydroabietic acid triarylamine compound a, the ultraviolet absorption spectrum of the compound d has a new absorption peak at 362-562nm, and the maximum absorption wavelength of the compound d is 428nm. The maximum fluorescence emission wavelength of the compound d is 594nm, which is red-shifted by 220nm compared with the maximum fluorescence emission wavelength (374 nm) of the compound a.
Description
Technical Field
The invention relates to a synthetic method of a series of D-pi-A type compounds taking dehydroabietic acid triarylamine compounds as electron-donating groups (D), benzene and derivatives thereof as pi bridges and cyanoacetic acid as electron-withdrawing groups (A), belonging to the field of organic synthesis.
Background
In recent years, with the huge consumption of traditional energy, the development and utilization of new energy become urgent tasks, and the utilization of solar energy is one of the main options for solving the problems of traditional energy. Dye-sensitized solar cells (DSSC) have reached 13% of maximum photoelectric conversion efficiency as 3 rd generation solar cells. The photoelectric conversion efficiency of the DSSC mainly depends on the dye, and factors such as the absorption performance of the dye, the difference in energy levels between HOMO (highest electron occupied orbital) and LUMO (lowest electron unoccupied orbital), the adsorption performance, and the photo-thermal stability all affect the efficiency of the DSSC. The dye sensitizer with better performance generally consists of an electron donor, a pi conjugated bridge and an electron acceptor (D-pi-A) through structural analysis, the structure is favorable for charge transfer, the structure is convenient to optimize, the electron donor, the pi conjugated system and the electron acceptor can be independently modified respectively, and extremely convenient conditions are created for researching the dependency relationship between the dye structure and the photoelectric conversion performance. At present, electron donors with better effects comprise triphenylamine, indoline, dimethyl fluorene substituted aniline and the like, and the donor units have adjusting effects on dye absorption spectra and molecular energy levels. Commonly used pi-conjugated bridges are thiophene, furan, pyrrole, benzene, and the like. The most commonly used molecular acceptor groups are carboxyl-containing groups such as cyanoacetic acid, rhodanic acid, etc. [ LiuB, zhuW, et al chemical Commun agents, 2009 (13): 1766; liuWH, wuIC, laiCH, et al. Chemnform, 2008,40 (41): 5152-5154; the journal of physical chemistry C,2009,113 (17): 7469-7479; ]. Triphenylamine has a non-coplanar propeller configuration, and when the triphenylamine is assembled on the optical electrode interface, energy loss caused by mutual stacking of dye molecules can be effectively avoided; the lone pair electrons on the nitrogen atom in the triphenylamine structure have conjugation with the big pi bond of 3 benzene rings, so the triphenylamine structure can be used as a strong electron donor to construct D-A and D-pi-A type compounds.
Two series of novel dehydroabietic acid triarylamine D-A structural compounds are designed and synthesized by using dehydroabietic acid triarylamine as a raw material, and the ultraviolet absorption spectrum and the fluorescence emission spectrum of the compounds are tested and are applied to OLED devices as hole transport materials. The ultraviolet absorption spectrum and the fluorescence emission spectrum of the compound are short, and particularly, the ultraviolet absorption wavelength is within 400nm, so that the requirement of applying the compound to a dye-sensitized solar cell cannot be met.
In order to expand the ultraviolet absorption range of the dehydroabietic acid triarylamine compound, the invention discloses a D-pi-A type compound which takes the dehydroabietic acid triarylamine compound as an electron-donating group (D), benzene and derivatives thereof as a pi bridge, and cyanoacetic acid as an electron-withdrawing group (A). The ultraviolet absorption wavelength and the fluorescence emission wavelength of the dehydroabietic acid triarylamine compound are expected to move towards the long wavelength direction, and the dehydroabietic acid triarylamine compound is applied to the aspects of dye-sensitized solar cells and molecular fluorescent probes.
Disclosure of Invention
The purpose of the invention is as follows: the invention provides a D-pi-A type compound which takes a dehydroabietic acid triarylamine compound as an electron-donating group (D), benzene and derivatives thereof as a pi bridge, and cyanoacetic acid as an electron-withdrawing group (A).
The technical scheme of the invention is as follows: the dehydroabietic acid triarylamine D-pi-A type compound takes a benzene derivative as a pi bridge, the dehydroabietic acid triarylamine compound is taken as an electron supply group (D), benzene and the derivative thereof are taken as the pi bridge, and cyanoacetic acid is taken as a D-pi-A type compound of an electron-withdrawing group (A), and the compound has a structure shown as the following formula:
wherein R is 1 Is any one of-H, methyl, methoxyl, hexyl, hexyloxy and benzene, or any one of an electron-donating substituent or an electron-withdrawing substituent;
R 2 is any one of-H, methyl, methoxyl, hexyl and hexyloxy, or any one of electron-donating groups.
The electron-donating substituent is any one of ethyl or isopropyl; the electron-withdrawing substituent is any one of nitro, cyano, bromine, chlorine, iodine and trifluoromethyl.
The preparation method of the dehydroabietic acid triarylamine D-pi-A type compound with the benzene derivative as the pi bridge comprises the steps of preparing a dehydroabietic acid triarylamine compound (I) and a dehydroabietic acid triarylamine D-pi-A type compound in acetonitrileNBS reaction to obtain bromo-dehydroabietic acid triarylamine compound (II), and reacting with bromo-dehydroabietic acid triarylamine compound (II) in organic solvent in the presence of nitrogen
Adding Pd catalyst and inorganic salt as raw materials, carrying out C-C coupling reaction in a mixed solution of organic solvent and water to obtain an intermediate compound (III), and then reacting with cyanoacetic acid to obtain a dehydroabietic acid triarylamine D-pi-A type compound (IV), wherein the formula is shown as follows:
the material molar ratio of NBS to dehydroabietic acid triarylamine compound (I) is 1:1
With bromo-dehydroabietic acid triarylamine compound (II)The ratio is 2:1;
the material mol ratio of the bromodehydroabietic acid triarylamine compound (II) to the bromodehydroabietic acid triarylamine compound is 2:1
Feed molar ratio to compound (V) 2:1; the molar ratio of the cyanoacetic acid to the (III) feed is 10:1.
the organic solvent is a mixture of any one of N, N-dimethylformamide, tetrahydrofuran, ethanol, chloroform, toluene, xylene, o-xylene or dioxane and water in any ratio.
The Pd catalyst is as follows: 1,1' -bis-diphenylphosphino ferrocene palladium dichloride, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride or palladium acetate.
The inorganic salt is any one of sodium carbonate, potassium carbonate and cesium carbonate.
The reaction temperature is 50-200 ℃, and the reaction time is 24 hours.
Has the beneficial effects that:
compared with the dehydroabietic acid triarylamine compound (I), the ultraviolet absorption spectrum of the compound (IV) has a new absorption peak at 362-562nm, and the maximum absorption wavelength of the compound (IV) is 428nm. The maximum fluorescence emission wavelength of the compound (IV) is 594nm, which is red-shifted by 220nm compared with the maximum fluorescence emission wavelength (374 nm) of the compound (I). The compound has better application performance in the field of dye-sensitized solar cells.
4. Description of the drawings
FIG. 1 shows a and d in dioxane solution (2X 10) -5 mol/L) of the ultraviolet absorption spectrum.
FIG. 2 shows a, d in dioxane solution (5X 10) -7 mol/L) fluorescence emission spectrum.
Detailed description of the preferred embodiments
The present invention will be described in detail below by way of examples, but the present invention is not limited to the following examples.
Dehydroabietic acid triarylamine compound (a) and NBS (N-bromosuccinimide) in acetonitrile) Reacting to obtain bromo-dehydroabietic acid triarylamine compound (b), and reacting in organic solvent in the presence of nitrogen to obtain bromo-dehydroabietic acid triarylamine compound (b) and
adding Pd catalyst and carbonate as raw materials, carrying out C-C coupling reaction in a mixed solution of an organic solvent and water to obtain an intermediate compound (C), and then reacting with cyanoacetic acid to obtain a dehydroabietic acid triarylamine D-pi-A type compound (D).
Example 1
The compound prepared in this example was:
the preparation process comprises the following steps:
in a first step, 0.73g of a compound a, in which R is 1 Is methoxy [ Burrows H D, castro R, esteves M A, et al. Materials Science Forum,2006,514-516.]0.25g of NBS and 100ml of anhydrous acetonitrile are added into a round-bottom flask, and the mixture is reacted for 24 hours at 25 ℃ in the dark, and subjected to rotary evaporation, column chromatography separation and purification (petroleum ether: ethyl acetate 20.
In the second step, 3.04g of Compound b, 0.14g of Pd (PPh) 3 ) 4 、12.71gNa 2 CO 3 Into a three-necked flask, 100ml of THF and 50ml of H were added 2 O, heating to 45 ℃ under nitrogen atmosphere, maintaining for 30 minutes, slowly adding 1.56g of a solution of 4-formylphenylboronic acid in 50ml of thf, heating under reflux for 12 hours, extracting with water and dichloromethane, collecting the organic phase, drying the organic phase with anhydrous magnesium sulfate, filtering, rotary-steaming, purifying by column chromatography (petroleum ether: ethyl acetate 10c, ginger yellow powder, the yield is 65.03%. Characterization data: IR upsilon max /cm -1 :2925,1723,1661,1598,1504,1441,1240； 1 H NMR(DMSO-d6,300MHz,ppm)δ:9.98(s,1H,CHO),7.91(d,J＝8.1Hz,2H,Ar-H),7.80(d,J＝8.2Hz,2H,Ar-H),7.59(d,J＝8.6Hz,2H,Ar-H),7.12–6.99(m,4H,Ar-H),6.99–6.85(m,2H,Ar-H),6.73(d,J＝8.5Hz,2H，Ar-H),3.72(d,J＝7.3Hz,3H，OCH 3 ),3.61(s,3H，CO 2 CH 3 ),3.12–2.70(m,3H，CH,CH 2 ),2.06(dd,J＝28.4,15.4Hz,2H,CH 2 ),1.78(dd,J＝19.2,11.7Hz,1H,CH),1.70–1.46(m,4H,CH 2 ),1.18(t,J＝17.7Hz,8H，CH 2 ,CH 3 ),0.95(s,6H,CH 3 )； 13 C NM R(DMSO-d6,75MHz,ppm)δ:195.36,180.99,158.49,152.27,151.77,148.64,146.65,143.68,142.17,137.18,136.72,133.19(2C),131.63,130.71(3C),129.01(3C),128.38(2C),128.28,120.32,117.78(2C),58.28,54.88,49.97,47.62,40.63,39.59,39.21,32.10,29.90,27.84,26.42(2C),24.10,20.93,19.29。
And a third step of adding 0.38g of the compound c, 0.15g of cyanoacetic acid, 0.65ml of piperidine and 20ml of chloroform into a three-neck flask, heating and refluxing (63 ℃) for 12 hours under a nitrogen atmosphere, cooling, extracting the chloroform with water, collecting an organic phase, drying over anhydrous magnesium sulfate, performing column chromatography separation and purification (eluent, dichloromethane: methanol 9:1), performing rotary evaporation, and drying in a vacuum drying oven to obtain 0.14g of the compound d, wherein the yield is 33.22%. Characterization data: IR upsilon max /cm -1 :2922.59,2223.52,1722.05,1579.16,1492.83,1240.81,1183.58； 1 H NMR(DMSO-d6,300MHz,ppm)δ:8.33(s,1H,CH),8.08(t,J＝19.1Hz,2H,Ar-H),7.84(d,J＝8.2Hz,2H,Ar-H),7.66(d,J＝8.5Hz,2H,Ar-H),7.16–7.01(m,4H,Ar-H),6.94(d,J＝8.6Hz,2H,Ar-H),6.75(d,J＝8.4Hz,2H,Ar-H),3.76(s,3H,CH 3 ),3.65(s,3H,CO 2 CH 3 ),3.05(dt,J＝13.3,6.6Hz,1H,CH),2.98–2.74(m,2H,CH 2 ),2.23–1.96(m,2H,CH 2 ),1.90–1.77(m,1H,CH),1.65(dd,J＝31.7,18.9Hz,4H,CH 2 ),1.24(d,J＝18.5Hz,5H,CH 2 ,CH 3 ),1.16(s,3H,CH 3 ),0.90(dd,J＝33.1,27.0Hz,6H,CH 3 )。
Example 2
The compound prepared in this example was:
the preparation process comprises the following steps:
the first step was the same as in example 1.
In the second step, 3.04g of compound b, 0.14g Pd (PPh) 3 ) 4 、12.71gNa 2 CO 3 Into a three-necked flask, 100ml of toluene and 50ml of H were added 2 O, heating to 45 ℃ under nitrogen atmosphere, maintaining for 30 minutes, slowly adding 1.56g of 4-formylphenylboronic acid in 50ml of toluene, heating under reflux for 12 hours, extracting with water and dichloromethane, collecting the organic phase, drying the organic phase with anhydrous magnesium sulfate, filtering, rotary-steaming, purifying by column chromatography (petroleum ether: ethyl acetate 10.
The third step is the same as that of example 1.
Example 3
The compound prepared in this example was:
the preparation process comprises the following steps:
the first step was the same as in example 1.
In the second step, 0.6g of Compound b, 0.5g
0.4g of potassium acetate, 0.05g of Pd (dppf) Cl 2 ·CH 2 Cl 2 15ml of DMSO was added to a three-necked flaskAnd heated to 80 ℃ under nitrogen atmosphere for 24 hours, cooled, extracted with water and dichloromethane, the organic phase collected, then dried over anhydrous magnesium sulfate, filtered, rotary evaporated, purified by column chromatography (petroleum ether: ethyl acetate 10) and dried in a vacuum oven to obtain 0.48g of compound g as a white powder with a yield of 73.17%.
In the third step, 1.3g of compound g and 0.06g of Pd (PPh) 3 ) 4 、5.09gNa 2 CO 3 Into a three-necked flask, 100ml of THF and 50ml of H were added 2 O, heating to 45 ℃ under nitrogen atmosphere, maintaining the temperature for 30 minutes, and slowly adding 0.81g of 4-bromo-3-methylbenzaldehyde (b)
Alatin) was heated under reflux for 12 hours, extracted with water and methylene chloride, the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, rotary-distilled, and purified by column chromatography (petroleum ether: ethyl acetate 10: 1) After rotary evaporation, the mixture is dried in a vacuum drying oven to obtain 0.78g of compound c and ginger yellow powder with the yield of 56.26%. Characterization data: IR upsilon max /cm -1 :2928,2048,1723,1691,1599,1504,1240； 1 H NMR(DMSO-d6,300MHz,ppm)δ:10.01(d,J＝20.0Hz,1H，CHO),7.93–7.66(m,2H,Ar-H),7.39(m,1H,Ar-H),7.19(d,J＝8.5Hz,2H,Ar-H),7.12–6.85(m,6H,Ar-H),6.71(t,J＝8.1Hz,2H,Ar-H),3.88–3.68(m,3H,OCH 3 ),3.60(s,3H,CO 2 CH 3 ),3.15–2.70(m,3H,CH,CH 2 ),2.47–2.25(m,3H,CH 3 ),2.08(t,J＝15.5Hz,2H,CH 2 ),1.90–1.74(m,1H,CH),1.61(dd,J＝18.7,9.6Hz,4H,CH 2 ),1.21(d,J＝17.3Hz,5H,CH 2 ,CH 3 ),1.11(s,3H,CH 3 ),0.95(s,6H,CH 3 )。
And a third step of adding 0.38g of the compound c, 0.15g of cyanoacetic acid, 0.65ml of piperidine and 20ml of chloroform into a three-neck flask, heating and refluxing (63 ℃) for 12 hours under a nitrogen atmosphere, cooling, extracting the chloroform with water, collecting an organic phase, drying over anhydrous magnesium sulfate, performing column chromatography separation and purification (eluent, dichloromethane: methanol 9:1), performing rotary evaporation, and drying in a vacuum drying oven to obtain 0.13g of the compound d, namely red powder, wherein the yield is 31.08%.
Claims (6)
1. The dehydroabietic acid triarylamine D-pi-A type compound taking the benzene derivative as a pi bridge is characterized in that the dehydroabietic acid triarylamine type compound is taken as an electron supply group (D), benzene and the derivative thereof are the pi bridge, and cyanoacetic acid is taken as a D-pi-A type compound of an electron-withdrawing group (A), and the compound has a structure shown as the following formula:
wherein R is 1 Is any one of-H, methyl, methoxyl, hexyl, hexyloxyl, benzene, ethyl, isopropyl, nitryl, cyano, bromine, chlorine, iodine and trifluoromethyl;
R 2 is any one of-H, methyl, methoxyl, hexyl, hexyloxyl, ethyl, isopropyl, nitryl, cyano, bromine, chlorine, iodine and trifluoromethyl.
2. The process for preparing the dehydroabietic acid triarylamine D-pi-A type compound having a benzene derivative as a pi bridge according to claim 1, wherein the dehydroabietic acid triarylamine compound (I) is reacted with NBS in acetonitrile to obtain a bromo-dehydroabietic acid triarylamine compound (II), and the bromo-dehydroabietic acid triarylamine compound (II) are reacted with NBS in an organic solvent in the presence of nitrogen in an organic solvent
Adding Pd catalyst and inorganic salt as raw materials, carrying out C-C coupling reaction in a mixed solution of organic solvent and water to obtain an intermediate compound (III), and then reacting with cyanoacetic acid to obtain a dehydroabietic acid triarylamine D-pi-A type compound (IV), wherein the formula is shown as follows:
or in the presence of nitrogen in the presence ofBromodehydroabietic acid triarylamine compound (II) and
as a raw material, pd (dppf) Cl is added 2 ·CH 2 Cl 2 And potassium acetate in DMSO solution to obtain intermediate compound (V), intermediate compound (V) and
the intermediate compound (III) is obtained by taking the raw materials, adding a Pd catalyst and inorganic salt, and carrying out C-C coupling reaction in a mixed solution of an organic solvent and water, and is shown as the following formula:
3. the process for the preparation of a dehydroabietic acid triarylamine D-pi-a type compound having a benzene derivative as a pi bridge according to claim 2, wherein the molar ratio of NBS to dehydroabietic acid triarylamine compound (I) is 1:1;
the material mol ratio of the bromodehydroabietic acid triarylamine compound (II) to the bromodehydroabietic acid triarylamine compound is 2:1;
the material mol ratio of the bromodehydroabietic acid triarylamine compound (II) to the bromodehydroabietic acid triarylamine compound is 2:1;
feed molar ratio to compound (V) 2:1; the molar ratio of the cyanoacetic acid to the (III) feed is 10:1.
4. the process for preparing a dehydroabietic acid triarylamine D-pi-a type compound having a benzene derivative as a pi bridge according to claim 2, wherein the organic solvent is a mixture of water and any one of N, N-dimethylformamide, tetrahydrofuran, ethanol, chloroform, toluene, xylene, o-xylene or dioxane in any ratio.
5. The process for preparing a dehydroabietic acid triarylamine D-pi-a type compound having a benzene derivative as a pi bridge according to claim 2, wherein the Pd-based catalyst is: 1,1' -bis-diphenylphosphino ferrocene palladium dichloride, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride or palladium acetate.
6. The process for producing a dehydroabietic acid triarylamine D-pi-a type compound having a benzene derivative as a pi bridge according to claim 2, wherein the inorganic salt is any one of sodium carbonate, potassium carbonate and cesium carbonate.
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|---|---|---|---|---|
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| CN103073444A (en) * | 2013-01-28 | 2013-05-01 | 中国林业科学研究院林产化学工业研究所 | Application of dehydroabietic acid based arylamine compound as hole transport material |
| CN103137875A (en) * | 2011-11-21 | 2013-06-05 | 柯尼卡美能达商用科技株式会社 | Photoelectric conversion element and solar battery containing the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN103137875A (en) * | 2011-11-21 | 2013-06-05 | 柯尼卡美能达商用科技株式会社 | Photoelectric conversion element and solar battery containing the same |
| CN103073444A (en) * | 2013-01-28 | 2013-05-01 | 中国林业科学研究院林产化学工业研究所 | Application of dehydroabietic acid based arylamine compound as hole transport material |
Non-Patent Citations (1)
| Title |
|---|
| A multi-sensing fluorescent compound derived from cyanoacrylic acid;Zhang, Xiqi 等;《Journal of Materials Chemistry》;20091109;第20卷(第2期);第292-298页 * |
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