CN114057774A - Organic photoelectric molecular material containing thienothiadiazole structure and preparation method and application thereof - Google Patents
Organic photoelectric molecular material containing thienothiadiazole structure and preparation method and application thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 37
- YCIFPAMAAWDQJS-UHFFFAOYSA-N thieno[2,3-d]thiadiazole Chemical group S1N=NC2=C1C=CS2 YCIFPAMAAWDQJS-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000001228 spectrum Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 17
- 229960001701 chloroform Drugs 0.000 claims description 15
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- IJOOHPMOJXWVHK-UHFFFAOYSA-N trimethylsilyl-trifluoromethansulfonate Natural products C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [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 8
- 230000035484 reaction time Effects 0.000 claims description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 5
- 239000001119 stannous chloride Substances 0.000 claims description 5
- 235000011150 stannous chloride Nutrition 0.000 claims description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 4
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- FIOJWGRGPONADF-UHFFFAOYSA-N (sulfinylamino)benzene Chemical compound O=S=NC1=CC=CC=C1 FIOJWGRGPONADF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 2
- 238000002156 mixing Methods 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
- 238000000862 absorption spectrum Methods 0.000 abstract description 10
- 230000008033 biological extinction Effects 0.000 abstract description 8
- 230000009286 beneficial effect Effects 0.000 abstract description 6
- 230000021615 conjugation Effects 0.000 abstract description 4
- GXCYSYAYMKUSRB-UHFFFAOYSA-N 2-(2-methylidene-3-oxoinden-1-ylidene)propanedinitrile Chemical compound C1=CC=C2C(=C(C#N)C#N)C(=C)C(=O)C2=C1 GXCYSYAYMKUSRB-UHFFFAOYSA-N 0.000 abstract description 3
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 238000004776 molecular orbital Methods 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 150000003577 thiophenes Chemical class 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000013086 organic photovoltaic Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QNVKZKOSAXYVFZ-UHFFFAOYSA-N 2-(3-oxoinden-1-ylidene)propanedinitrile Chemical compound C1=CC=C2C(=O)CC(=C(C#N)C#N)C2=C1 QNVKZKOSAXYVFZ-UHFFFAOYSA-N 0.000 description 1
- FKMLTPDJPCYVHT-UHFFFAOYSA-N 2-(5,6-difluoro-3-oxoinden-1-ylidene)propanedinitrile Chemical compound FC=1C=C2C(CC(C2=CC=1F)=C(C#N)C#N)=O FKMLTPDJPCYVHT-UHFFFAOYSA-N 0.000 description 1
- LXELBQMGKYWFHS-UHFFFAOYSA-N 2-methylideneindene-1,3-dione Chemical compound C1=CC=C2C(=O)C(=C)C(=O)C2=C1 LXELBQMGKYWFHS-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000004297 night vision Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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Abstract
The invention belongs to the field of organic photoelectric materials, and particularly relates to an organic photoelectric molecular material containing a thienothiadiazole structure, and a preparation method and application thereof. The invention adopts thienothiadiazole as a central unit, thiophene derivatives as a connecting unit, and 2- (2-methylene-3-oxo-2, 3-dihydro-1H-indene-1-ylidene) malononitrile or 2-methylene-1H-indene-1, 3(2H) -diketone as a terminal structure; therefore, the method has good planarity, can form good conjugation, is beneficial to delocalization of molecular orbitals, improves the extinction coefficient of molecules, and promotes the separation and transmission of charges. The prepared organic photoelectric molecule has an absorption spectrum range exceeding 1.1 mu m, is beneficial to further spectrum expansion, retains the advantages of high crystallinity and high near infrared extinction coefficient, is easily dissolved in an organic solvent, and can be used for preparing a high-quality film by a solution method. Has important significance for developing the development and application of the wide-spectrum organic near-infrared detector.
Description
Technical Field
The invention belongs to the field of organic photoelectric materials, and particularly relates to an organic photoelectric molecular material containing a thienothiadiazole structure, and a preparation method and application thereof.
Background
Compared with the traditional inorganic near-infrared detector, the organic near-infrared detector has multiple advantages in technical difficulty, material cost and application scene because the organic near-infrared detector can be prepared on the flexible substrate in a large area by a simple and cheap solution film-forming technology, and challenges the traditional inorganic detector in the aspects of image sensing, biomedical detection, optical communication, environment monitoring, night vision, remote control and the like. Over the last two decades, organic near-infrared light detectors based on near-infrared polymer donors have attracted much attention, however, the performance of the near-infrared light detectors is not ideal.
In recent years, organic near-infrared light detectors based on near-infrared small molecule receptor materials have shown great advantages. The material has better crystallinity, high extinction coefficient in a near infrared band, and high external quantum efficiency and specific detectivity of a device in the near infrared band (adv. mater.2020, 32.1906027). However, the structure type of the materials developed at present is single, and the materials mostly adopt a conjugated or condensed ring thiophene unit as a core, and both ends adopt a molecular structure of receptor unit end capping; the absorption spectrum range of the organic near infrared detector is more than 1.1 mu m, and the application scene of the organic near infrared detector is severely limited.
Disclosure of Invention
Aiming at the problems or the defects, the invention provides an organic photoelectric molecular material containing a thienothiadiazole structure and a preparation method and application thereof, aiming at solving the problems of the existing organic photoelectric material such as shortage of types and relatively small absorption spectrum, wherein the organic photoelectric molecular material takes thienothiadiazole as a center, the thiophene structure is connected, and 2- (2-methylene-3-oxo-2, 3-dihydro-1H-indene-1-subunit) malononitrile or 2-methylene-1H-indene-1, 3(2H) -diketone is used as a tail end; is soluble in common organic solvents (such as trichloromethane, tetrahydrofuran and toluene), is easy to prepare, and can prepare high-quality films for application to organic photodetectors by a solution method.
An organic photoelectric molecular material containing a thienothiadiazole structure has a structural general formula shown in formula I:
in the formula I, A adopts oxygen or dicyanomethylene; x and Y are hydrogen, fluorine, chlorine, bromine or methyl, and X and Y are different; d is a thiophene conjugated unit with electron donating ability.
Further, the thiophene conjugated unit D with the electron donating ability adopts one of the following structures:
wherein R is1With C1-C20 alkyl radicals, R2、R3、R4、R5、R6And R7With hydrogen, C1-C20 alkyl or C1-C20 alkoxy, and R2、R3、R4、R5、R6And R7May be the same or different.
The preparation method of the organic photoelectric molecular material containing the thienothiadiazole structure comprises the following steps:
The catalyst is tetrakis (triphenylphosphine) palladium, palladium acetate or dichlorobis (triphenylphosphine) palladium; the organic solvent is toluene, chlorobenzene or o-dichlorobenzene; d is a thiophene conjugated unit with electron donating ability.
The organic solvent is methanol, ethanol or tetrahydrofuran, and the concentration of concentrated hydrochloric acid is more than or equal to 10 percent by mass percent.
And 3, preparing a compound shown as a formula IV: and (3) completely dissolving the compound of the formula V obtained in the step (2), the N-sulfinanilide and the trimethyl silicon chloride in an organic solvent according to a feeding molar ratio of 1: 5-30: 10-60, and performing reflux reaction at 25-100 ℃ for 1-8 hours in an inert atmosphere to obtain the compound.
The organic solvent is triethylamine, piperidine or pyridine.
And 4, preparing a compound shown as a formula II: and (3) dissolving the compound shown in the formula IV obtained in the step (3) and N, N-dimethylformamide in an organic solvent, and dropwise adding phosphorus oxychloride at the temperature of-20-0 ℃ for carrying out an acylation reaction for 1-4 hours to obtain the compound shown in the formula II.
The feeding molar ratio of the compound shown in the formula IV, N-dimethylformamide and phosphorus oxychloride is 1: 20-40: 40-80; the organic solvent is tetrahydrofuran, dichloromethane or 1, 2-dichloroethane.
and (3) completely dissolving the compound shown in the formula II and the compound shown in the formula III obtained in the step (4) in a reaction solvent according to the feeding molar ratio of 1: 2-1: 10, and adding a catalyst to perform reflux reaction at the temperature of 30-80 ℃ for 6-48 hours to obtain the compound.
The catalyst is triethylamine, pyridine or piperidine; the reaction solvent is trichloromethane, tetrahydrofuran or 1, 2-dichloroethane. In the formula III, A adopts oxygen or dicyanomethylene; x and Y are hydrogen, fluorine, chlorine, bromine or methyl, and X and Y are different.
Further, in the step 1: the feeding molar ratio of the compounds of the formula VII and the formula VIII is 1:3, the reaction temperature is 110 ℃, the reaction time is 36 hours, the organic solvent is toluene, and the catalyst is tetrakis (triphenylphosphine) palladium.
Further, in the step 2: the feeding molar ratio of the compound shown in the formula VI to the stannous chloride to the concentrated hydrochloric acid is 1:20: 60, taking tetrahydrofuran as an organic solvent, and reacting at 25 ℃ for 72 hours.
Further, in the step 3: the feeding molar ratio of the compound shown in the formula V, the N-sulfinylaniline and the trimethyl silicon chloride is 1:10:20, the organic solvent is pyridine, the reaction temperature is 80 ℃, and the reaction time is 4 hours.
Further, in the step 4: the feeding molar ratio of the compound shown in the formula IV, N-dimethylformamide and phosphorus oxychloride is 1:20: 40; the organic solvent is 1, 2-dichloroethane; the reaction temperature was 0 ℃ and the reaction time was 2 hours.
Further, in the step 5: the feeding molar ratio of the compound shown in the formula II to the compound shown in the formula III is 1:8, the reaction temperature is 65 ℃, the reaction time is 6 hours, the catalyst is pyridine, and the reaction solvent is trichloromethane.
The soluble organic photoelectric molecule shown in the formula I is used as a receptor material to prepare a near-infrared and/or wide-spectrum organic photodetector. In particular to the preparation of a photodiode type or a phototransistor type organic light detector.
The thienothiadiazole is a strong receptor unit with quinoid structure effect, and the structure is introduced as a skeleton unit in the design of conjugated molecules, so that the molecular band gap can be obviously reduced. Meanwhile, the double five-membered ring structure of the thienothiadiazole has good planarity and small volume steric hindrance characteristics, and can remarkably enhance the conjugation degree of molecules and improve the solubility of the molecules. The design of applying the thienothiadiazole unit to a near-infrared small molecule receptor material is not available.
The invention provides a method for using quinoid unit thienothiadiazole with strong electron deficiency characteristics in the design of organic photoelectric molecules, wherein the thienothiadiazole is used as a central unit, a thiophene derivative is used as a connecting unit, and the tail end structure is 2- (2-methylene-3-oxo-2, 3-dihydro-1H-indene-1-ylidene) malononitrile or 2-methylene-1H-indene-1, 3(2H) -diketone; therefore, the method has good planarity, can form good conjugation, is beneficial to delocalization of molecular orbitals, improves the extinction coefficient of molecules, and promotes the separation and transmission of charges. The novel near-infrared small molecule receptor photoelectric detection material is easy to realize ultra-narrow band gap, is beneficial to further spectrum expansion, the absorption spectrum range of the prepared organic photoelectric molecule exceeds 1.1 mu m, and the advantages of high crystallinity and high near-infrared extinction coefficient are kept, thereby having important significance for developing and applying a wide-spectrum organic near-infrared detector.
In conclusion, the absorption spectrum range of the organic photoelectric molecular material containing the thienothiadiazole structure provided by the invention is more than 1.1 μm, the advantages of high crystallinity and high near-infrared extinction coefficient are retained, the organic photoelectric molecular material has good solubility in conventional organic solvents (such as trichloromethane, tetrahydrofuran and toluene), and a high-quality film can be prepared by a solution method. The molecular material has good application prospect in the aspect of preparing near-infrared or wide-spectrum organic photoelectric detectors.
Drawings
FIG. 1 is a synthesis scheme of TTD1 as an organic photovoltaic molecule in example 1;
FIG. 2 is a synthesis scheme of TTD2 as an organic photovoltaic molecule in example 2;
FIG. 3 is a solution and thin film absorption spectrum of TTD1 in examples 1 and 2;
fig. 4 shows absorption spectra of the solution and the thin film of the organic photovoltaic molecule TTD2 in examples 1 and 2.
Detailed Description
The principles and features of this invention are described in further detail below with reference to the accompanying drawings and examples, which are provided for illustration only and are not intended to limit the scope of the invention. The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1, synthesis of TTD 1:
the chemical reaction scheme is shown in figure 1, and the specific reaction steps and reaction conditions are as follows:
preparation of compound 2 (compound numbered 2 in fig. 1): to a solution of compound 1(1.38g,2mmol) and compound 2(232.4mg, 0.7mmol) in dry toluene (15ml) under an inert atmosphere was added Pd (PPh)3)4(34.8mg,0.03 mmol). The whole reaction system was heated to 110 ℃ and stirred for 48 hours. After the reaction solution was cooled, the organic phase was rotary evaporated to remove the solvent, and the mixture was purified by distillation using petroleum ether: dichloromethane (10:1) was used as eluent and the column was chromatographed on silica gel, and the solvent was removed by rotary evaporation to give Compound 2(560mg, 82%) as a solid, MALDI-TOF MS: m/z 975.6.
Preparation of compound 3 (compound numbered 3 in fig. 1): under an inert atmosphere, a solution of compound 2(390.2mg,0.4mmol) and concentrated hydrochloric acid (8mmol) in tetrahydrofuran (20mL) was cooled to 0 deg.C and stannous chloride (4.55g, 24mmol) was added in portions with stirring. The solution was warmed to room temperature and stirred for 72 hours. The reaction mixture was poured into 100ml of ice-water mixture and 1mol/L NaOH solution was slowly added to alkalinity. Extracted with dichloromethane and dried over anhydrous magnesium sulfate. The organic phase was rotary evaporated to remove the solvent and to give Compound 3(292.9mg, 80%) as an oil, MALDI-TOF MS: m/z 915.5.
Preparation of compound 4 (compound numbered 4 in fig. 1): a solution of compound 3(292.9mg,0.32mmol) and sulfinanilide (445.4mg,3.2mmol) in 5mL of pyridine was heated to 80 ℃ under an inert atmosphere and the reaction was stirred for 1 hour. Chlorotrimethylsilane (695.3mg,6.4mmol) was slowly added dropwise, and the reaction was stirred for 0.5 hour. The reaction solution was cooled to room temperature, and the reaction was stirred at that temperature for 16 hours. The reaction was poured into 150ml of ice-water mixture and 1M HCl was slowly added to acidity. Extracted with dichloromethane and dried over anhydrous magnesium sulfate. The organic phase was rotary evaporated to remove the solvent, and the eluate was eluted with petroleum ether on a silica gel column to give Compound 4(193.2mg, 64%) as an oil (MALDI-TOF MS: m/z 943.6).
Preparation of compound 5 (compound numbered 5 in fig. 1): under an inert atmosphere, a solution of compound 4(193.2mg,0.2mmol) and N, N-dimethylformamide (733mg, 10mmol) in 1, 2-dichloroethane (20mL) was cooled to 0 ℃ and phosphorus oxychloride (4.6g, 30mmol) was added dropwise slowly with stirring and stirred at that temperature for 1 h. The reaction solution was poured into a saturated sodium carbonate solution, extracted with dichloromethane, washed with water three times, and dried over anhydrous magnesium sulfate. The organic phase was rotary evaporated to remove the solvent, and the mixture was dried in petroleum ether: dichloromethane (1:1) was used as eluent and the column was chromatographed on silica gel, and the solvent was removed by rotary evaporation to give Compound 5(104mg, 52%) as a solid, MALDI-TOF MS: m/z 999.6.
Preparation of TTD 1: under an inert atmosphere, 2- (3-oxo-2, 3-dihydro-1H-inden-1-ylidene) malononitrile (116.4mg,0.6mmol) was added to a solution of compound 5(100mg,0.1mmol) and pyridine (0.2mL,2.5mmol) in anhydrous chloroform (25mL), and the mixture was heated to 65 ℃ and stirred for 6 hours. Cooling the reaction solution, adding methanol for precipitation, centrifuging, dissolving the solid part with chloroform, washing with water for three times, and drying with anhydrous magnesium sulfate. The organic phase was rotary evaporated to remove the solvent, and the mixture was dried in petroleum ether: chloroform (1:1) as eluent, and silica gel column chromatography for separating the product. The product was recrystallized from chloroform and methanol, dichloromethane to give TTD1(90.7mg, 67%) as a black solid product, MALDI-TOF MS: m/z 1351.9.
Example 2 Synthesis of TTD2
The chemical reaction scheme is shown in figure 1, wherein the synthesis of compound 5 is the same as that of example 1, and the preparation reaction steps and reaction conditions of compound TTD2 are as follows:
under an inert atmosphere, 2- (5, 6-difluoro-3-oxo-2, 3-dihydro-1H-inden-1-ylidene) malononitrile (138mg,0.6mmol) was added to a solution of compound 5(100mg,0.1mmol) and pyridine (0.2mL,2.5mmol) in anhydrous chloroform (25mL), and the mixture was heated to 65 ℃ and stirred for 6 hours. Cooling the reaction solution, adding methanol for precipitation, centrifuging, dissolving the solid part with chloroform, washing with water for three times, and drying with anhydrous magnesium sulfate. The organic phase was rotary evaporated to remove the solvent, and the mixture was dried in petroleum ether: chloroform (1:1) as eluent, and silica gel column chromatography for separating the product. The product was recrystallized from chloroform and methanol, dichloromethane to give TTD2(91.1mg, 64%) as a black solid product, MALDI-TOF MS: m/z 1424.2.
Example 3, ultraviolet-visible-near infrared absorption spectra of the organic photoelectric molecules TTD1 and TTD2 prepared in examples 1 and 2 in a thin film state were measured.
Organic photoelectric molecules TTD1 and TTD2 are dissolved in chloroform to prepare a solution with the concentration of 20mg/mL, and part of the solution is taken to spin on a quartz plate to prepare a film. The absorption spectra of these samples in the thin film state are shown in FIG. 3, and both exceed 1.1. mu.m.
The above examples show that the quinoid unit thienothiadiazole with strong electron deficiency is used in the design of organic photoelectric molecules, the thienothiadiazole is used as a central unit, the thiophene derivative is a connecting unit, and the terminal structure is 2- (2-methylene-3-oxo-2, 3-dihydro-1H-indene-1-ylidene) malononitrile or 2-methylene-1H-indene-1, 3(2H) -dione; the material has good planarity, can form good conjugation, is beneficial to delocalization of molecular orbitals, improves the extinction coefficient of molecules, and promotes the separation and transmission of charges; the prepared organic photoelectric molecule has an absorption spectrum range exceeding 1.1 mu m, is beneficial to further spectrum expansion, retains the advantages of high crystallinity and high near-infrared extinction coefficient, and has good application prospect in the aspect of preparing near-infrared or wide-spectrum organic photoelectric detectors.
Claims (10)
1. An organic photoelectric molecular material containing a thienothiadiazole structure is characterized in that:
the structural general formula is shown as formula I:
in the formula I, A adopts oxygen or dicyanomethylene; x and Y are hydrogen, fluorine, chlorine, bromine or methyl, and X and Y are different; d is a thiophene conjugated unit with electron donating ability.
2. The organic photoelectric molecular material containing a thienothiadiazole structure of claim 1, wherein:
the thiophene conjugated unit D with the electron donating ability adopts one of the following structures:
wherein R is1With C1-C20 alkyl radicals, R2、R3、R4、R5、R6And R7With hydrogen, C1-C20 alkyl or C1-C20 alkoxy, and R2、R3、R4、R5、R6And R7May be the same or different.
3. The preparation method of the organic photoelectric molecular material containing the thienothiadiazole structure as claimed in claim 1, characterized by comprising the steps of:
step 1, preparing a compound shown as a formula VI: completely dissolving a compound shown as a formula VII and a compound shown as a formula VIII in an organic solvent according to a feeding molar ratio of 1: 2-6, adding a catalyst, and reacting for 12-72 hours at 100-120 ℃ in an inert atmosphere to obtain the compound shown as the formula VII;
the catalyst is tetrakis (triphenylphosphine) palladium, palladium acetate or dichlorobis (triphenylphosphine) palladium; the organic solvent is toluene, chlorobenzene or o-dichlorobenzene; d is a thiophene conjugated unit with electron donating ability;
step 2, preparing a compound shown as a formula V: and (3) mixing the compound of the formula VI obtained in the step (1), stannous chloride and concentrated hydrochloric acid according to a feeding molar ratio of 1: 10-30: 50-500 of the organic solvent is completely dissolved in the organic solvent, and the mixture reacts for 12-72 hours at 0-60 ℃ in an inert atmosphere to obtain the organic solvent;
the organic solvent is methanol, ethanol or tetrahydrofuran;
and 3, preparing a compound shown as a formula IV: completely dissolving the compound of the formula V obtained in the step 2, N-sulfinanilide and trimethyl silicon chloride in an organic solvent according to a feeding molar ratio of 1: 5-30: 10-60, and performing reflux reaction at 25-100 ℃ for 1-8 hours in an inert atmosphere to obtain the compound;
the organic solvent is triethylamine, piperidine or pyridine;
and 4, preparing a compound shown as a formula II: dissolving the compound shown in the formula IV obtained in the step 3 and N, N-dimethylformamide in an organic solvent, and dropwise adding phosphorus oxychloride under an ice bath condition of-20-0 ℃ for carrying out an acylation reaction for 1-4 hours to obtain a compound shown in a formula II;
the feeding molar ratio of the compound shown in the formula IV, N-dimethylformamide and phosphorus oxychloride is 1: 20-40: 40-80; the organic solvent is tetrahydrofuran, dichloromethane or 1, 2-dichloroethane;
step 5, preparing the organic photoelectric molecular material containing the thienothiadiazole structure shown in the formula I;
completely dissolving the compound shown in the formula II and the compound shown in the formula III obtained in the step 4 in a reaction solvent according to a feeding molar ratio of 1: 2-1: 10, and adding a catalyst to perform reflux reaction at 30-80 ℃ for 6-48 hours to obtain the compound shown in the formula III;
the catalyst is triethylamine, pyridine or piperidine; the reaction solvent is trichloromethane, tetrahydrofuran or 1, 2-dichloroethane; in the formula III, A adopts oxygen or dicyanomethylene; x and Y are hydrogen, fluorine, chlorine, bromine or methyl, and X and Y are different.
4. The method for preparing the organic photoelectric molecular material containing the thienothiadiazole structure as claimed in claim 3, wherein the method comprises the following steps:
in the step 1: the feeding molar ratio of the compounds of the formula VII and the formula VIII is 1:3, the reaction temperature is 110 ℃, the reaction time is 36 hours, the organic solvent is toluene, and the catalyst is tetrakis (triphenylphosphine) palladium.
5. The method for preparing the organic photoelectric molecular material containing the thienothiadiazole structure as claimed in claim 3, wherein the method comprises the following steps:
in the step 2: the feeding molar ratio of the compound shown in the formula VI to the stannous chloride to the concentrated hydrochloric acid is 1:20: 60, taking tetrahydrofuran as an organic solvent, and reacting at 25 ℃ for 72 hours.
6. The method for preparing the organic photoelectric molecular material containing the thienothiadiazole structure as claimed in claim 3, wherein the method comprises the following steps:
in the step 3: the feeding molar ratio of the compound shown in the formula V, the N-sulfinylaniline and the trimethyl silicon chloride is 1:10:20, the organic solvent is pyridine, the reaction temperature is 80 ℃, and the reaction time is 4 hours.
7. The method for preparing the organic photoelectric molecular material containing the thienothiadiazole structure as claimed in claim 3, wherein the method comprises the following steps:
in the step 4: the feeding molar ratio of the compound shown in the formula IV, N-dimethylformamide and phosphorus oxychloride is 1:20: 40; the organic solvent is 1, 2-dichloroethane; the reaction temperature was 0 ℃ and the reaction time was 2 hours.
8. The method for preparing the organic photoelectric molecular material containing the thienothiadiazole structure as claimed in claim 3, wherein the method comprises the following steps:
in the step 5: the feeding molar ratio of the compound shown in the formula II to the compound shown in the formula III is 1:8, the reaction temperature is 65 ℃, the reaction time is 6 hours, the catalyst is pyridine, and the reaction solvent is trichloromethane.
9. The method for applying the organic photoelectric molecular material containing the thienothiadiazole structure as claimed in claim 1, wherein the method comprises the following steps: the soluble organic photoelectric molecule shown in the formula I is used as a receptor material to prepare a near-infrared and/or wide-spectrum organic photodetector.
10. The method for applying the organic photoelectric molecular material containing the thienothiadiazole structure as claimed in claim 9, wherein: the organic light detector is a photodiode type or a phototransistor type organic light detector.
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