CN114230506B - Triphenylamine compound containing maleimide, and preparation method and application thereof - Google Patents
Triphenylamine compound containing maleimide, and preparation method and application thereof Download PDFInfo
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- CN114230506B CN114230506B CN202111542285.8A CN202111542285A CN114230506B CN 114230506 B CN114230506 B CN 114230506B CN 202111542285 A CN202111542285 A CN 202111542285A CN 114230506 B CN114230506 B CN 114230506B
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- -1 Triphenylamine compound Chemical class 0.000 title claims abstract description 47
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 13
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 238000004440 column chromatography Methods 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 9
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003495 polar organic solvent Substances 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 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
- 238000000926 separation method Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 206010070834 Sensitisation Diseases 0.000 abstract description 2
- 238000012216 screening Methods 0.000 abstract description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 238000005259 measurement Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000010183 spectrum analysis Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000001819 mass spectrum Methods 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000002105 nanoparticle Substances 0.000 description 8
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 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 description 5
- 101150003085 Pdcl gene Proteins 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- 238000013461 design Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JUWYQISLQJRRNT-UHFFFAOYSA-N (5-formylfuran-2-yl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)O1 JUWYQISLQJRRNT-UHFFFAOYSA-N 0.000 description 1
- ISHFYECQSXFODS-UHFFFAOYSA-M 1,2-dimethyl-3-propylimidazol-1-ium;iodide Chemical compound [I-].CCCN1C=C[N+](C)=C1C ISHFYECQSXFODS-UHFFFAOYSA-M 0.000 description 1
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- ZJYYHGLJYGJLLN-UHFFFAOYSA-N guanidinium thiocyanate Chemical compound SC#N.NC(N)=N ZJYYHGLJYGJLLN-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Hybrid Cells (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a triphenylamine compound containing maleimide, a preparation method and a co-sensitization application thereof, wherein the chemical structural formula of the triphenylamine compound containing maleimide is shown as the formula (I):
in the formula (I), the substituent R 1 Is n-butyl or phenyl; substituent R 2 Is any one of the following three types:
Description
Technical Field
The invention relates to a triphenylamine compound containing maleimide, a preparation method and application thereof.
Background
Dye Sensitized Solar Cells (DSSC) are receiving attention because of their advantages such as low cost of production, ease of manufacture, and high photoelectric conversion efficiency. Dye sensitizers are an important component of DSSCs, and researchers have designed and synthesized a large variety of dye sensitizers. In the design strategy of dye sensitizers, changing the electron donor has a significant impact on the performance of the dye sensitizer. Triphenylamine and derivatives thereof with excellent charge transport capability are the most used electron donors in the design and development of dye sensitizers.
Maleimide groups, which have excellent thermo-mechanical properties and biological activity, as well as a unique advantage as dienophiles in the Diels-Alder reaction, have been recognized as one of the most useful synthetic scaffolds in organic chemistry. Maleimide and aryl (hetero) ring bond are connected as bridge bond, introduced into triphenylamine donor, and cyanoacetic acid is used as acceptor, so that novel triphenylamine dye sensitizer is expected to be obtained.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide a triphenylamine compound containing maleimide, a preparation method and application thereof.
The invention discloses a triphenylamine compound containing maleimide, which is characterized in that the chemical structural formula is shown as the formula (I):
in the formula, the substituent R 1 Is n-butyl or phenyl; substituent R 2 Is any one of the following three types:
further, the invention also discloses a preparation method of the triphenylamine compound containing maleimide, which is characterized by comprising the following steps:
1) Dissolving a compound shown in a formula (III), tetratriphenylphosphine palladium and an aryl boric acid compound in tetrahydrofuran under the protection of nitrogen to obtain a solution, mixing the obtained solution with a potassium carbonate aqueous solution, and carrying out heating reflux reaction to obtain a compound shown in a structural formula (II), wherein the structural formula of the aryl boric acid compound is shown in a formula (IV), a formula (V) or a formula (VI):
in the formula, a substituent R 1 Is n-butyl or phenyl;
substituent R 3 The structural formula of (A) is any one of the following three types:
2) Under the protection of nitrogen, carrying out reflux reaction on a compound shown as a formula (II), a carboxylic acid compound and an organic alkaline compound in a polar organic solvent, and after the reaction is finished, carrying out post-treatment on a reaction solution to obtain a triphenylamine compound containing maleimide shown as a formula (I);
in the formula (I), the substituent R 1 Is n-butyl or phenyl; substituent R 2 Is any one of the following three types:
further, the invention also defines that the organic basic compound in the step 2) is piperidine; the carboxylic acid compounds are cyanoacetic acid; the molar ratio of the compound shown as the formula (II), the carboxylic acid compound and the organic alkaline compound is 1:4 to 6:9 to 12; the polar organic solvent is at least one of chloroform and acetonitrile, preferably a mixed solvent of chloroform and acetonitrile; the ratio of the amount of the substance of the compound represented by the formula (II) to the volume of the polar organic solvent is 1; the temperature of the reflux reaction is 60-90 ℃, and the time of the reflux reaction is 7-12 h; the post-treatment of the reaction solution comprises the following steps: the reaction liquid is dried by spinning, and then column chromatography separation is carried out to obtain a target product, namely the triphenylamine compound containing the maleimide as shown in the formula (I); the eluent used for column chromatography separation is a mixed solution of dichloromethane and methanol.
Furthermore, the invention also defines the application of the triphenylamine compound containing maleimide as a raw material in the preparation of the dye-sensitized solar cell, and the application specifically comprises the following steps: the triphenylamine compound containing maleimide and the ruthenium metal dye Z907 are dissolved in an organic solvent to prepare a solution for soaking TiO 2 And the electrode is assembled into a dye-sensitized solar cell for photoelectric conversion, wherein the amount ratio of the triphenylamine compound containing maleimide to the ruthenium metal dye Z907 is 1:1, organic solvent is 1:10 of a mixed solvent of methanol and chloroform, the concentration of the solution is 3 x 10 -4 mol/L。
The above-mentioned maleimide-containing triphenylamine compound and TiO of ruthenium metal dye Z907 2 The electrode and the platinum counter electrode are assembled to form a sandwich structure, and electrolyte (namely TiO loaded with triphenylamine compound containing maleimide) is dripped into the sandwich structure 2 An electrode sandwiching an electrolyte with a platinum counter electrode). In the present invention, the electrolyte includes a solution of 1, 2-dimethyl-3-propylimidazolium iodide, iodine, lithium iodide, guanidinium thiocyanate and 4-tert-butylpyridine in acetonitrile.
By adopting the technology, compared with the prior art, the invention has the following beneficial effects: the triphenylamine compound containing maleimide is synthesized by a limited method, the triphenylamine compound containing maleimide is taken as a donor, phenyl, thienyl and furyl are taken as bridge bonds, cyanoacetic acid is taken as an acceptor, and the triphenylamine dye sensitizer containing maleimide is synthesized, the compound is taken as a co-sensitizer of ruthenium metal dye Z907 and acts on TiO with the ruthenium metal dye Z907 2 The dye-sensitized solar cell assembled by the electrode has better photoelectric conversion efficiency which is 2.17-7.27 percent and is ruthenium goldThe screening of the co-sensitizing agent belonging to the dye Z907 adds a new applicable substance.
Detailed Description
The invention is further illustrated with reference to the following specific examples, without limiting the scope of the invention thereto.
Example 1 a maleimide-containing triphenylamine compound represented by the formula (Ia) was prepared according to the following reaction formula:
the preparation method of the triphenylamine compound containing the maleimide as shown in the formula (Ia) comprises the following steps:
under the protection of nitrogen, compound IIIa (505mg, 1.06mmol), 4-formylphenylboronic acid IV (237.5mg, 1.59mmol) and Pd (PPh) 3 ) 4 (61mg, 0.05mmol) was dissolved in THF (16 mL) and K was added 2 CO 3 A solution of (440mg, 3.18 mmol) in water (4 mL) was refluxed for 24 hours. After completion of the reaction, the reaction mixture was poured into 200mL of water, extracted with DCM (80 mL. Times.3), and the organic phases were combined and washed with saturated brine (100 mL. Times.3). After removal of the solvent in vacuo, the mixture is purified by column chromatography (V) DCM :V PE 1) = 2); purification gave a red solid (458.9mg, 86.3%) of the compound of formula (IIa). The melting point is 90-91 ℃.
The nuclear magnetic spectrum analysis of the obtained compound having the structure represented by the formula (IIa) showed the following results: 1 HNMR(500MHz,CDCl 3 )δ10.04(s,1H),7.90(d,J＝8.3Hz,2H),7.71(d,J＝8.2Hz,2H),7.40(d,J＝8.9Hz,2H),7.31(t,J＝7.9Hz,4H),7.16(d,J＝7.6Hz,4H),7.12(t,J＝7.4Hz,2H),6.93(d,J＝8.9Hz,2H),3.66(t,J＝7.2Hz,2H),1.73-1.63(m,2H),1.39(dt,J＝14.6,7.4Hz,2H),0.97(t,J＝7.3Hz,3H)；
measurement result HRMS (ESI) m/z calcd for C of high-resolution electron impact mass spectrum (HREIMS) 33 H 28 N 2 O 3 Na + (M+Na) + 523.1998,found 523.1993.
Under the protection of nitrogen, compound IIa (252mg, 0.50mmol), cyanoacetic acid(216mg, 2.52mmol) and 0.5mL of piperidine were added to a Schlenk's tube, 6mL of acetonitrile was added, and the reaction was refluxed for 9 hours. After the reaction is complete, the solvent is removed in vacuo and the mixture is subjected to column chromatography (V) DCM :V CH3OH = 10) purification to give the compound of structural formula (Ia) as a red solid (227.1mg, 79.5%). The melting point is 158-159 ℃.
The obtained compound having the structure represented by formula (Ia) was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,DMSO)δ7.94-7.87(m,3H),7.54(d,J＝8.4Hz,2H),7.38-7.37(m,3H),7.36-7.34(m,3H),7.15(d,J＝7.4Hz,2H),7.13-7.10(m,4H),6.85(d,J＝8.9Hz,2H),3.53(t,J＝7.1Hz,2H),1.61-1.54(m,2H),1.34-1.29(m,2H),0.91(t,J＝7.3Hz,3H).
measurement result HRMS (ESI) m/z calcd for C of high-resolution electron impact mass spectrum (HREIMS) 36 H 29 N 3 O 4 Na + (M+Na) + 590.2056,found 590.2044.
Example 2
The reaction formula for preparing the triphenylamine compound containing the maleimide as shown in the formula (Ib) is as follows:
the preparation method of the triphenylamine compound containing the maleimide as shown in the formula (Ib) comprises the following steps:
under the protection of nitrogen, compound IIIa (200mg, 0.42mmol), 5-aldehyde-2-thiopheneboronic acid V (98.4 mg, 0.63mmol) and PdCl 2 (dppf) (24mg, 0.021mmol) was dissolved in THF (8 mL) and K was added 2 CO 3 (176mg, 1.26mmol) in water (2 mL) was refluxed for 24h. After completion of the reaction, the reaction mixture was poured into 200mL of water, extracted with DCM (80 mL. Times.3), and the organic phases were combined and washed with saturated brine (100 mL. Times.3). After removal of the solvent in vacuo, the mixture is purified by column chromatography (V) DCM :V PE = 3). The melting point is 93-94 ℃.
Subjecting the obtained compound having the structure represented by formula (IIb) to nuclear magnetic spectrum analysis,the results are as follows: 1 H NMR(500MHz,CDCl 3 )δ9.93(s,1H),7.86(d,J＝4.1Hz,1H),7.69(d,J＝4.1Hz,1H),7.49-7.43(m,2H),7.36-7.32(m,4H),7.24-7.18(m,4H),7.15(t,J＝7.4Hz,2H),7.07-7.01(m,2H),3.65(t,J＝7.2Hz,2H),1.71-1.62(m,2H),1.42-1.34(m,2H),0.97(t,J＝7.4Hz,3H).
measurement result of high resolution electron bombardment mass spectrum (HREIMS) HRMS (ESI) m/z calcd for C 31 H 26 N 2 O 3 SNa + (M+Na) + 529.1562,found 529.1551.
Compound IIb (13mg, 0.026mmol), cyanoacetic acid (1113mg, 0.13mmol), piperidine (25. Mu.L), chloroform 0.5mL, and acetonitrile 1mL were added to a Schlenk tube under nitrogen, and the reaction was refluxed for 7 hours. After the reaction is complete, the solvent is removed in vacuo and the mixture is subjected to column chromatography (V) DCM :V CH3OH = 10) purification to give the compound violet black solid as shown in structural formula (Ib) (12.9mg, 87.9%). The melting point is 137-138 ℃.
The obtained compound having the structure represented by formula (Ib) was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,DMSO)δ8.15(s,1H),7.80(d,J＝4.1Hz,1H),7.72(d,J＝4.0Hz,1H),7.44(d,J＝8.7Hz,2H),7.38(t,J＝7.9Hz,4H),7.17-7.13(m,6H),6.98(d,J＝8.7Hz,2H),3.52(t,J＝6.9Hz,2H),1.60-1.54(m,2H),1.34-1.28(m,2H),0.91(t,J＝7.3Hz,3H).
measurement result of high resolution electron bombardment mass spectrum (HREIMS) HRMS (ESI) m/z calcd for C 34 H 27 N 3 O 4 SNa + (M+Na) + 596.1620,found 596.1609.
Example 3
The reaction formula for preparing the triphenylamine compound containing the maleimide as shown in the formula (Ic) is as follows:
the preparation method of the triphenylamine compound containing the maleimide as shown in the formula (Ic) comprises the following steps:
under the protection of nitrogen, compound IIIa (200mg, 0.42mmol),5-Formylfuran-2-boronic acid VI (88.4 mg, 0.63mmol) and PdCl 2 (dppf) (24mg, 0.02mmol) was dissolved in THF (8 mL) and K was added 2 CO 3 (176mg, 1.26mmol) in water (2 mL) and reacted for 24h under reflux. After completion of the reaction, the reaction mixture was poured into 300mL of water, extracted with ethyl acetate (80 mL. Times.3), and the organic phases were combined and washed with saturated brine (100 mL. Times.3). After removal of the solvent in vacuo, the mixture is purified by column chromatography (V) DCM :V PE = 3) purification to give the compound as shown in structural formula (iic) as a purple solid (180.5mg, 87.5%). The melting point is 100-101 ℃.
The nuclear magnetic spectrum analysis of the compound having the structure represented by formula (IIc) obtained showed the following results: 1 H NMR(500MHz,CDCl 3 )δ9.61(s,1H),7.64-7.60(m,2H),7.52(d,J＝3.8Hz,1H),7.37-7.31(m,5H),7.23(dd,J＝8.5,1.0Hz,4H),7.17-7.12(m,2H),7.10-7.05(m,2H),3.65(t,J＝7.2Hz,2H),1.63-1.59(m,2H),1.42-1.34(m,2H),0.97(t,J＝7.4Hz,3H).
measurement result HRMS (ESI) m/z calcd for C of high-resolution electron impact mass spectrum (HREIMS) 31 H 26 N 2 O 4 Na + (M+Na) + 513.1785,found 513.1790.
Under the protection of nitrogen, compound IIc (14mg, 0.03mmol), cyanoacetic acid (12.2mg, 0.14mmol), piperidine 25. Mu.L, and chloroform 1.5mL were added to schlenk tube, and the reaction was refluxed for 12 hours. After the reaction is complete, the solvent is removed in vacuo and the mixture is subjected to column chromatography (V) DCM :V CH3OH = 10) purification to give the compound of structural formula (Ic) as a purple black solid (9.74mg, 61.2%). The melting point is 179-180 ℃.
The obtained compound having the structure represented by formula (Ic) was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,DMSO)δ7.84(s,1H),7.58-7.51(m,3H),7.46(d,J＝3.9Hz,1H),7.37(t,J＝8Hz,4H),7.19-7.16(m,4H),7.14(t,J＝7.4Hz,2H),6.96(d,J＝8.9Hz,2H),3.52(t,J＝7.0Hz,2H),1.59-1.53(m,2H),1.34-1.26(m,2H),0.90(t,J＝7.4Hz,3H).
measurement result of high resolution electron bombardment mass spectrum (HREIMS) HRMS (ESI) m/z calcd for C 34 H 27 N 3 O 5 Na + (M+Na) + 580.1848,found 580.1833.
Example 4
The reaction formula for preparing the triphenylamine compound containing the N-phenylmaleimide as shown in the formula (Id) is as follows:
the preparation method of the triphenylamine compound containing the N-phenylmaleimide as shown in the formula (Id) comprises the following steps:
under nitrogen protection, compound IIIb (50mg, 0.10mmol), 4-formylphenylboronic acid (22.4mg, 0.15mmol), pdCl 2 (dppf)(3.7mg,0.005mmol)，K 2 CO 3 (41.4mg, 0.30mmol) was added to a Schlenk tube and the reaction was refluxed for 12 hours. After completion of the reaction, the reaction mixture was poured into 100mL of water, extracted with dichloromethane (50 mL. Times.3), and the organic phases were combined and washed with saturated brine (100 mL. Times.3). After removal of the solvent in vacuo, by column chromatography (V) DCM :V PE = 2) purification to give the compound of formula (iid) as a red solid (47.1mg, 89.8%). The melting point is 111-112 ℃.
The obtained compound having the structure represented by the formula (Id) was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,CDCl 3 )δ10.06(s,1H),7.93(d,J＝8.4Hz,2H),7.77(d,J＝8.3Hz,2H),7.52(t,J＝7.5Hz,2H),7.47-7.44(m,4H),7.34-7.31(m,5H),7.18(d,J＝9.0Hz,4H),7.14(t,J＝7.4Hz,2H),6.94(d,J＝9.0Hz,2H).
measurement result of high resolution electron bombardment mass spectrum (HREIMS) HRMS (ESI) m/z 543.1674[ m + Na ]] + ,Calcd for C 35 H 24 N 2 O 3 Na:543.1679
Compound IId (50mg, 0.10 mmol), cyanoacetic acid (43.2mg, 0.50mmol), piperidine 0.1mL, chloroform 1mL, and acetonitrile 2mL were added to a Schlenk tube under nitrogen, and the mixture was heated at 70 ℃ for 12 hours. After the reaction is complete, the solvent is removed in vacuo and the mixture is purified by column chromatography (V) DCM :V CH3OH = 10) purification to give the compound as shown in structural formula (Id) as a red solid (43.3mg, 76.4%). The melting point is 101-102 ℃.
The obtained compound having the structure represented by the formula (Id) was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,DMSO)δ7.94-7.92(m,3H),7.60(d,J＝8.5Hz,2H),7.56-7.51(m,2H),7.48-7.45(m,2H),7.45-7.42(m,1H),7.42-7.34(m,6H),7.18-7.12(m,6H),6.87(d,J＝9.0Hz,2H)
measurement result HRMS (ESI) m/z 610.1733[ 2 ] M + Na of high resolution electron bombardment mass spectrometry (HREIMS)] + ,Calcd for C 38 H 25 N 3 O 4 Na:610.1737.
Example 5
The reaction formula for preparing the triphenylamine compound containing the N-phenylmaleimide as shown in the formula (Ie) is as follows:
the preparation method of the triphenylamine compound containing the N-phenylmaleimide as shown in the formula (Ie) comprises the following steps:
under the protection of nitrogen, compound IIIb (50mg, 0.10mmol), 5-aldehyde-2-thiopheneboronic acid (23.4mg, 0.15mmol), pdCl 2 (dppf)(3.7mg,0.005mmol)，K 2 CO 3 (41.4mg, 0.3mmol) was added to a Schlenk's tube and the reaction was refluxed for 12 hours. After completion of the reaction, the reaction mixture was poured into 100mL of water, extracted with DCM (50 mL. Times.3), and the organic phases were combined and washed with saturated brine (100 mL. Times.3). After removal of the solvent in vacuo, by column chromatography (V) DCM :V PE = 2) purification to give the compound as shown in structural formula (ie) as a violet solid (48.1mg, 90.3%). The melting point is 93-94 ℃.
The obtained compound having the structure represented by the formula (IIe) was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,CDCl 3 )δ9.96(s,1H),7.92(d,J＝4.1Hz,1H),7.73(d,J＝4.1Hz,1H),7.54-7.49(m,4H),7.47-7.44(m,2H),7.41(t,J＝7.3Hz,1H),7.38-7.33(m,4H),7.24-7.22(m,4H),7.16(t,J＝7.4Hz,2H),7.08-7.05(m,2H).
measurement result HRMS (ESI) m/z 549.1238[ m + Na ] of high resolution electron bombardment mass spectrometry (HREIMS)] + ,Calcd for C 33 H 22 N 2 O 3 SNa:549.1243.
Under the protection of nitrogen, compound IIe (103mg, 0.20mmol), cyanoacetic acid (108mg, 1.20mmol), piperidine (0.2 mL) and acetonitrile (3 mL) were added to a Schlenk tube, and the mixture was heated at 90 ℃ for reaction for 8h. After the reaction is complete, the solvent is removed in vacuo and the mixture is subjected to column chromatography (V) DCM :V CH3OH = 10) purification to give the compound purple black solid as shown in structural formula (Ie) (83.2mg, 73.9%). The melting point is 93-94 ℃.
The obtained compound having the structure represented by formula (Ie) was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,DMSO)δ8.03(s,1H),7.83(d,J＝4.1Hz,1H),7.67(d,J＝4.1Hz,1H),7.57-7.41(m,7H),7.40-7.37(m,4H),7.21-7.13(m,6H),7.04-6.97(m,2H).
measurement result HRMS (ESI) m/z 616.1294[ M + Na ] of high resolution electron bombardment mass spectrum (HREIMS)] + ,Calcd for C 36 H 23 N 3 O 4 SNa:616.1302
Example 6
The reaction formula for preparing the triphenylamine compound containing the N-phenylmaleimide as shown in the formula (If) is as follows:
the preparation method of the triphenylamine compound containing the N-phenylmaleimide as shown in the formula (If) comprises the following steps:
under nitrogen protection, compound IIIb (50mg, 0.10mmol), 5-aldehyde furan-2-boronic acid (21.0mg, 0.15mmol), pdCl 2 (dppf)(3.7mg,0.005mmol)，K 2 CO 3 (41.4mg, 0.3mmol) was added to a Schlenk tube and the reaction was refluxed for 12 hours. After completion of the reaction, the reaction mixture was poured into 100mL of water, extracted with DCM (50 mL. Times.3), and the organic phases were combined and washed with saturated brine (100 mL. Times.3). After removal of the solvent in vacuo, the mixture is purified by column chromatography (V) DCM :V PE = 2). The melting point is 119-120 ℃.
Conversion of the resulting structure having the formula (IIf)The compound was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,CDCl 3 )δ9.64(s,1H),7.70-7.65(m,2H),7.58(d,J＝3.8Hz,1H),7.54-7.49(m,2H),7.46-7.40(m,3H),7.38-7.33(m,5H),7.27-7.23(m,4H),7.16(t,J＝7.4Hz,2H),7.13-7.07(m,2H).
measurement result of high resolution electron bombardment mass spectrum (HREIMS) HRMS (ESI) m/z 533.1468[ m + Na ] m/z] + ,Calcd for C 33 H 22 N 2 O 4 Na:533.1472.
Under the protection of nitrogen, compound IIf (89mg, 0.17mmol), cyanoacetic acid (76.36mg, 0.87mmol), piperidine 0.2mL, and chloroform 4mL were added to a Schlenk tube, and the reaction was heated at 65 ℃ for 10 hours. After the reaction is complete, the solvent is removed in vacuo and the mixture is subjected to column chromatography (V) DCM :V CH3OH = 10) purification to give the compound as shown in structural formula (If) as a purple black solid (78.1mg, 77.6%). The melting point is 130-131 ℃.
The obtained compound having the structure represented by formula (If) was subjected to nuclear magnetic spectrum analysis, and the results were as follows: 1 H NMR(500MHz,DMSO)δ7.58-7.50(m,5H),7.48(t,J＝3.8Hz,1H),7.46-7.38(m,8H),7.19(d,J＝7.7Hz,4H),7.14(t,J＝7.3Hz,2H),6.99(d,J＝8.8Hz,2H).
measurement result of high resolution electron bombardment mass spectrum (HREIMS) HRMS (ESI) m/z 600.1522[ m + Na ]] + ,Calcd for C 36 H 23 N 3 O 5 Na:600.1530.
Example 7: the triphenylamine compound containing maleimide is used as a co-sensitizer of ruthenium metal dye:
firstly, the maleimide-containing triphenylamine compounds prepared in examples 1 to 6 and ruthenium metal dye Z907 are mixed in a mass ratio of 1:1, mixing, dissolving in a solvent with a volume ratio of 10:1 CHCl 3 Mixing with methanol to obtain dye sensitizer solution (concentration of compound is 3 × 10) -4 mol·L -1 )。
Double-layer TiO prepared by screen printing 2 The nano particle film is used as a photoelectrode and comprises the following steps:
1) Firstly, printing a layer of 20nm TiO with the thickness of 12 mu m on a conductive glass FTO 2 Particles, calcined in a muffle furnace at 450 ℃Burning for 30min, and soaking in 0.04 mol.L -1 TiCl concentration 4 Pretreating in water solution at 70 deg.C for 30min to obtain double-layer TiO 2 A nanoparticle film. Then taking out the double-layer TiO 2 Washing the nano particle film with water and ethanol respectively, and drying with a hair drier;
2) Drying the double-layer TiO dried in the step 1) 2 Calcining the nano particle film in a muffle furnace at 450 ℃ for 30min again, cooling to 80 ℃, immersing the nano particle film into the prepared dye sensitizer solution, standing at room temperature for 24 hours for sensitization, and taking out the double-layer TiO 2 Washing the nano particle film with ethanol and drying to obtain the double-layer TiO 2 Nanoparticle film photoelectrodes.
Preparation of platinum counter electrode: using a screen printing method to print H 2 PtCl 6 And printing the aqueous solution on FTO conductive glass, and sintering for 20min in a muffle furnace at 400 ℃ to obtain the platinum counter electrode.
Double layer of TiO 2 The nano particle membrane photoelectrode and the platinum counter electrode are assembled into a sandwich structure, electrolyte is dripped into the edge of the sandwich structure, and the electrolyte is introduced into the sandwich structure by utilizing the capillary penetration principle. At 100mW/cm 2 Under the irradiation of light intensity, the photo-voltage-current characteristic curve is measured. The results are shown in table 1:
TABLE 1 DSSC Performance parameters assembled from maleimide-containing triphenylamine compounds and ruthenium metal dye Z907
In Table 1, a: jsc is short-circuit current density; voc is open-circuit voltage; ff is a filling factor; and d is the photoelectric conversion efficiency.
The description is given for the sole purpose of illustrating the invention concept in its implementation form and the scope of the invention should not be considered as being limited to the particular form set forth in the examples.
Claims (10)
1. The triphenylamine compound containing maleimide is characterized in that the chemical structural formula is shown as the formula (I):
in the formula, a substituent R 1 Is n-butyl or phenyl; substituent R 2 Is any one of the following three types:
2. a method for producing a maleimide-containing triphenylamine compound according to claim 1, characterized by comprising the steps of:
1) Dissolving a compound shown in a formula (III), tetratriphenylphosphine palladium and an aryl boric acid compound in tetrahydrofuran under the protection of nitrogen to obtain a solution, mixing the obtained solution with a potassium carbonate aqueous solution, and carrying out heating reflux reaction to obtain a compound shown in a structural formula (II), wherein the structural formula of the aryl boric acid compound is shown in a formula (IV), a formula (V) or a formula (VI):
in the formula, a substituent R 1 Is n-butyl or phenyl;
substituent R 3 The structural formula of (A) is any one of the following three types:
2) Under the protection of nitrogen, carrying out reflux reaction on a compound shown as a formula (II), a carboxylic acid compound and an organic alkaline compound in a polar organic solvent, and after the reaction is finished, carrying out post-treatment on a reaction solution to obtain a triphenylamine compound containing maleimide shown as a formula (I), wherein the carboxylic acid compound is cyanoacetic acid;
in the formula (I), the substituent R 1 Is n-butyl or phenyl; substituent R 2 Is any one of the following three types:
3. the method for producing maleimide-containing triphenylamine compounds according to claim 2, wherein the organic basic compound in the step 2) is piperidine; the molar ratio of the compound shown as the formula (II), the carboxylic acid compound and the organic alkaline compound is 1:4 to 6:9 to 12.
4. The method for producing maleimide-containing triphenylamine compounds according to claim 2, wherein the polar organic solvent in the step 2) is at least one of chloroform and acetonitrile; the ratio of the amount of substance of the compound represented by the formula (II) to the volume of the polar organic solvent is 1.
5. The method for producing maleimide-containing triphenylamine compounds according to claim 4, wherein the polar organic solvent in the step 2) is a mixed solvent of chloroform and acetonitrile.
6. The method for preparing triphenylamine compounds containing maleimide in accordance with claim 2, wherein the temperature of the reflux reaction in step 2) is 60 to 90 ℃, and the time of the reflux reaction is 7 to 12 hours.
7. The method for producing maleimide-containing triphenylamine compounds according to claim 2, wherein the step of post-treating the reaction solution in the step 2) is: spin-drying the reaction liquid with a solvent, and then performing column chromatography separation to obtain a target product, namely the maleimide-containing triphenylamine compound shown as the formula (I); the eluent used for column chromatography separation is a mixed solution of dichloromethane and methanol.
8. Use of the maleimide-containing triphenylamine compound according to claim 1 in the preparation of dye-sensitized solar cells.
9. The use according to claim 8, characterized in that the maleimide-containing triphenylamine compound and the ruthenium metal dye Z907 are dissolved in an organic solvent to prepare a solution, and the obtained solution is soaked in TiO 2 And the electrodes are assembled into the dye-sensitized solar cell for photoelectric conversion.
10. Use according to claim 9, characterized in that the ratio of the amount of maleimide-containing triphenylamine compound to the amount of ruthenium metal dye Z907 species is 1:1, organic solvent is 1:10 of a mixed solvent of methanol and chloroform, the concentration of the solution is 3 x 10 -4 mol/L。
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