CN105175455B - Water-soluble bipyridyl-ruthenium class the photosensitizer and its application in dye-sensitized solar cells that imidazoles is cation - Google Patents
Water-soluble bipyridyl-ruthenium class the photosensitizer and its application in dye-sensitized solar cells that imidazoles is cation Download PDFInfo
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- CN105175455B CN105175455B CN201510557794.6A CN201510557794A CN105175455B CN 105175455 B CN105175455 B CN 105175455B CN 201510557794 A CN201510557794 A CN 201510557794A CN 105175455 B CN105175455 B CN 105175455B
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- C—CHEMISTRY; METALLURGY
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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
- H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
- H01G9/2013—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte the electrolyte comprising ionic liquids, e.g. alkyl imidazolium iodide
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
- H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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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- 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
-
- 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
- Y02E10/549—Organic PV cells
Abstract
Molecular structure, water solubility and its application in dye-sensitized solar cells for the water-soluble photosensitizers that the present invention relates to one kind using imidazoles as cation.By introducing glyoxaline cation, solve bipyridyl-ruthenium class photosensitizer water solubility problems, and with water instead of there are commonly solvents to configure solution, colorant as titanium dioxide photo anode, adsorbance is bigger, adsorption time faster, solves the problems, such as that other photosensitizer aqueous solutions cannot colour or meet water decolorization.Compared with other various bipyridyls-ruthenium class photosensitizer, heretofore described photosensitizer water solubility is greatly increased；Nano-titanium dioxide light anode can be coloured in aqueous solution, avoid largely using organic solvent in cell manufacturing process, reduce costs, improve environment and biocompatibility；The nano-titanium dioxide light anode coloured is not easy to be improved the service life of battery by water decolorization；Prepared dye-sensitized solar cells photoelectric conversion efficiency is more than 10%, same level is in N3 and N719 etc. outstanding photosensitizer, solving the problems, such as that other dye-sensitized solar cells are met during the preparation process aqueous can substantially reduce, preparation process difficulty is reduced, there is huge value in practical application and industrial production.
Description
Technical field
It is cationic water-soluble bipyridyl-ruthenium class photosensitizer molecular structure, water that the present invention relates to one kind with imidazoles
Dissolubility and its application in dye-sensitized solar cells.
Background technique
Solar energy is considered as effective substitution of traditional fossil energy as a kind of clean energy resource.Dye-sensitized cell has
The advantages that manufacture craft is relatively easy, energy conversion efficiency is higher, cost is relatively low has very strong application prospect.[referring to:
Hagfeldt,A.,Boschloo,G.；Sun,L.,Kloo.L.,Pettersson,H.,Chem.Rev.2010,110,6595].
1993, SwitzerlandThe dye-sensitized solar cells photoelectricity that professor etc. reports famous photosensitizer N3 production turns
It changes efficiency and has reached 10.3%.[referring to: Nazeeruddin, M.K.；Kay,A.,Rodicio,L.；Humphry-Baker,R.；
MRller,E.；Liska,P.；Vlachopoulos,N.；M.J.Am.Chem.Soc.1993,115,6382.].It connects
Get off, the seminar also by by two hydrogen cations in N3 photosensitizer replace with tetrabutyl amino cation obtain it is another
A famous photosensitizer N719, photoelectric conversion efficiency have reached 11%, it is most common to become field of dye-sensitized solar cells
Photosensitizer.[referring to: (a) Nazeeruddin, M.K.；Zakeeruddin,S.M.；Humphry-Baker,R.；Jirousek,
M.；Liska,P.；Vlachopoulos,N.；Shklover,V.；Fischer Christian-H.,
M.Inorg.Chem.1999,38,6298；(b)Nazeeruddin,M.K.；Angelis,F.D.；Fantacci,S.；
Selloni,A.；Viscardi,G.；Liska,P.；Ito,S.；Takeru,B.；M.J.Am.Chem.Soc.2005,
127,16835.]。
But it is insoluble in water by the bipyridyl of representative-ruthenium class photosensitizer of N3 and N719, mainly it is prepared into organic solvent
To pigmented with titanium dioxide after solution.A large amount of uses of organic solvent can not look down upon to potential threat caused by environment and biology.This
Outside, the titanium dioxide coloured be also easy to meet water decolorization, this make finished product solar cell properties exposing to the weather drench with rain from
Inevitable rapid decay in right environment.Unquestionably, photosensitizer water solubility problems are solved, and make pigmented with titanium dioxide process
It carries out in aqueous solution, can not only reduce cost, but also more friendly for environment and biology, it is raw in practical application and industry
Huge value will be generated in production.
Summary of the invention
It is an object of the invention to develop water-soluble bipyridyl-ruthenium class photosensitizer that imidazole is cation, solve
Photosensitizer water solubility problems, while solving the problems, such as that titanium dioxide colours in the aqueous solution of photosensitizer, and apply it to height
It imitates in dye-sensitized solar cells, acquisition is more than 10% photoelectric conversion efficiency.
The present invention solves the problems, such as this technical solution: by introducing glyoxaline cation, enhancing cis--bis- (isothiocyano)
Bis- (2,2'- bipyridyl -4,4'- dicarboxyl) ruthenium (II) class photosensitizers are water-soluble, with water instead of there are commonly solvent configurations
Colorant of the solution of photosensitizer as titanium dioxide photo anode, adsorbance is bigger, and adsorption time faster, is solved over photosensitive
The aqueous solution of agent cannot colour or decolourize serious problem.
Such imidazoles is the general structure of the water-soluble photosensitizers of cation are as follows:
Wherein R1For hydrogen, alkyl, alkoxy, benzyl, ether chain, alkylthio group, thioether chain, substituted aryl, substituted heteroaryl；R2
For hydrogen, alkyl, alkoxy, benzyl, ether chain, alkylthio group, thioether chain, substituted aryl, substituted heteroaryl, aldehyde radical, alkynyl, carbonyl,
Ester group, cyano, nitro；R3For hydrogen, alkyl, alkoxy, benzyl, ether chain, alkylthio group, thioether chain, substituted aryl, replace heteroaryl
Base；Wherein alkyl, alkoxy, benzyl, ether chain, alkylthio group, thioether chain, substituted aryl, substituted heteroaryl, alkynyl, carbonyl, ester group
In carbochain be one or more of straight chain, branch or cycloalkane that carbon number is 0~40.
The raw material and preparation route (such as attached drawing 1) of use:
(1) bromo imidazoles is dissolved in methanol and is reacted with the methanol solution of potassium hydroxide, obtained after insoluble matter is filtered
The methanol solution of hydroxide imidazoles；
(2) cis--bis- (isothiocyano) bis- (2,2'- bipyridyl -4,4'- dicarboxyl) rutheniums (II) are dissolved in methanol, added
Enter the methanol solution of the hydroxide imidazoles of 4 times of equivalents, then the aqueous solution of nitric acid is added dropwise to suitable pH value, after methanol is concentrated
Be added ether, product be precipitated, be dried in vacuo imidazoles be cation bipyridyl-ruthenium class photosensitizer.Wherein, hydroxide imidazoles
General structure are as follows:
Wherein R1For hydrogen, alkyl, alkoxy, benzyl, ether chain, alkylthio group, thioether chain, substituted aryl, substituted heteroaryl；R2
For hydrogen, alkyl, alkoxy, benzyl, ether chain, alkylthio group, thioether chain, substituted aryl, substituted heteroaryl, aldehyde radical, alkynyl, carbonyl,
Ester group, cyano, nitro；R3For hydrogen, alkyl, alkoxy, benzyl, ether chain, alkylthio group, thioether chain, substituted aryl, replace heteroaryl
Base；Wherein alkyl, alkoxy, benzyl, ether chain, alkylthio group, thioether chain, substituted aryl, substituted heteroaryl, alkynyl, carbonyl, ester group
In carbochain be one or more of straight chain, branch or cycloalkane that carbon number is 0~40.
With nuclear magnetic resonance spectroscopy (1H NMR) and high resolution mass spectrum confirm imidazoles be cation bipyridyl-ruthenium class
The structure of dyestuff.Detect instrument are as follows: Bruker AV II-400MHz type Nuclear Magnetic Resonance, wherein TMS is internal standard, deuterated
DMSO is solvent；Waters-Q-TOF-Premier (ESI) type high-resolution mass spectrometer.
Imidazoles is that bipyridyl-ruthenium class photosensitizer of cation has good water solubility.
Nano-titanium dioxide light anode has in bipyridyl-ruthenium class photosensitizer aqueous solution that imidazoles is cation inhales
Attached rate is fast, large amount of adsorption, adsorbs stable feature.The adsorption time for reaching optimum efficiency is only -3 hours 1 hour.
Imidazoles is the incident monochromatic photon-electron transformation efficiency curve covering of bipyridyl-ruthenium class photosensitizer of cation
300nm-750nm reaches as high as 80%-90%.
Imidazoles is bipyridyl-ruthenium class photosensitizer photoelectric conversion efficiency of cation up to 10%-11%, open-circuit voltage
Up to 0.74-0.78V, short circuit current is up to 19-22mA/cm2, fill factor is up to 68-75%.
In the embodiment of the present invention, the Kapton Tape of titanium dioxide photo anode, platinum electrode and 30 μ m thicks is outsourcing.
Titanium dioxide photo anode specification are as follows: it is 13~15 μm that a layer thickness is covered on electro-conductive glass, and area is 0.4 × 0.4cm2Two
TiOx nano particle.
The photoelectric property of dye-sensitized cell characterizes instrument are as follows: monochromatic photon-electron transformation efficiency is in QTest
It is tested on Station 1000AD (Crowntech, Inc.), photoelectric conversion efficiency Oriel 94023A, Newport Corp.
It is 100mW cm that solar simulator, which provides power,-2Under conditions of, light is measured with 2000 type current potential table of Keithley Series
Current density voltage curve.
Compared with various bipyridyls-ruthenium class photosensitizer of preparation dye-sensitized solar cells, with imidazoles in the present invention
Water-soluble bipyridyl-ruthenium class photosensitizer performance for cation is more excellent, embodies are as follows:
1. imidazoles is that water-soluble bipyridyl-ruthenium class photosensitizer water solubility of cation greatly increases；
2. imidazoles is that water-soluble bipyridyl-ruthenium class photosensitizer of cation can be in aqueous solution to nano-titanium dioxide light
Anodic coloration avoids largely using organic solvent in cell manufacturing process, reduces costs, improve environment and bio-compatible
Property；
3. the nano-titanium dioxide light anode that water-soluble bipyridyl-ruthenium class photosensitizer with imidazoles for cation colours is not
It is easy to improve the service life of battery by water decolorization；
4. with the water-soluble bipyridyl that imidazoles is cation-ruthenium class photosensitizer preparation dye-sensitized solar cells light
Photoelectric transformation efficiency is more than 10%, is in same level with N3 and N719 etc. outstanding photosensitizer, solves other dye sensitizations too
Positive energy battery performance meets the problem of water substantially reduces in preparing cell process, reduces preparation process difficulty.
Four, Detailed description of the invention
Fig. 1 is bipyridyl-ruthenium class photosensitizer synthetic route that imidazoles is cation；
Fig. 2 is the molecular structure and hydrogen nuclear magnetic resonance spectrogram of M2C6 synthesized by the embodiment of the present invention 1；
Fig. 3 is the monochromatic photon-electron transformation efficiency figure of M2C6 synthesized by the embodiment of the present invention 1；
Fig. 4 is density of photocurrent-voltage pattern of M2C6 synthesized by the embodiment of the present invention 1.
Five, specific embodiment
Below with reference to specific implementation case, the invention will be further described, it will help the understanding of the present invention.But simultaneously
It cannot be used as a limitation interest field of the invention, and interest field of the invention should be subject to what claims illustrated.
The synthesis of embodiment 1:M2C6
(1) bromo 3- n-hexyl -1,2- methylimidazole (522.4mg, 2mmol, one times of equivalents) is dissolved in methanol
Potassium hydroxide (117.8mg, 2.1mmol, 1.05 times of equivalents) is separately dissolved in methanol by (1mL), and the methanol solution of potassium hydroxide is dripped
The methanol solution of bromo 3- n-hexyl -1,2- methylimidazole is added, is stirred 12 hours at room temperature.It must be clarified after suction filtration molten
Liquid, filtered solution methanol dilution to 8mL, being configured to the n-hexyl of 3- containing hydroxide -1,2- methylimidazole concentration is
The methanol solution of 0.25mmol/mL.
(2) by cis--bis- (isothiocyano) bis- (2,2'- bipyridyl -4,4'- dicarboxyl) rutheniums (II) (211.7mg,
0.3mmol, 1.0 times of equivalents) it is dissolved in methanol (5mL), hydroxide 3- n-hexyl -1,2- dimethyl obtained in step (1) is added
The methanol solution (4.8mL, 1.2mmol, 4.0 times of equivalents) of imidazoles 0.25mmol/mL, ether is added after 1 hour in stirring at normal temperature
Solid is precipitated in (20mL), and solid 310mg is obtained after being filtered with Buchner funnel, solid is dissolved in methanol (10mL), and 4.3mL concentration is added
For the nitric acid methanol solution of 0.1mol/L, it is concentrated into 2mL, is added ether (10mL), solid is precipitated, and filters and is dried in vacuo, obtains
Black solid M2C6 (153.6mg, yield: 48.0%).1H NMR(400MHz,CDCl3): δ=0.84 (t, J=6.2Hz, 6H),
1.20-1.30 (m, 12H), 1.67 (t, J=6.8Hz, 4H), 2.57 (m, 6H), 3.74 (s, 6H), 4.09 (t, J=7.4Hz,
4H), 7.41-7.45 (m, 4H), 7.63 (2.0Hz, 2H), 7.66 (d, J=2.0Hz, 2H), 8.08 (dd, J=5.6Hz,
1.2Hz, 2H), 8.53 (s, 2H), 8.70 (s, 2H), 9.17 (d, J=5.6Hz, 2H) ppm. (attached drawing 2)
Embodiment 2: the solubility test of photosensitizer in water
It at most can dissolve M2C6 synthesized by 83.1mg embodiment 1 in 10.0mL water, obtain dark red solution, thus calculate
The solubility of M2C6 in water is 8.3mg/mL.
Embodiment 3: the assembling of dye-sensitized solar cells
M2C6 synthesized by embodiment 1 (8.00mg) is dissolved in distilled water (14.5mL), is used under the monitoring of pH meter
The aqueous solution of nitric acid of 0.010M adjusts the pH to 3.8 of the aqueous solution of M2C6, and the concentration of photosensitizer is 0.50mmol/L at this time, will receive
Rice titanium dioxide photo anode immerses, and room temperature takes out after 2 hours, with distilled water flushing, dries under the conditions of 80 DEG C.Polyamides is used again
Imines adhesive tape bonds the titanium dioxide photo anode coloured and platinum electrode, injects electrolyte solution, prepares dye sensitization too
Positive energy battery.
Embodiment 4: dye-sensitized solar cells photoelectric property characterization
Room temperature condition, obtained dye-sensitized solar cells monochrome photon-electron converts effect in testing example 3
Rate.The monochromatic photon-electron transformation efficiency peak value for measuring dye-sensitized solar cells is 90% (such as attached drawing 3)；Room temperature condition,
In 100mW cm-2Under the solar simulator irradiation of power and 1.5G irradiation, the dye sensitization sun obtained in testing example 3
It can battery parameter.The photoelectric conversion efficiency 10.6% of dye-sensitized solar cells is measured, wherein open-circuit voltage 0.74V, short circuit
Current density 21.2mA/cm-2, fill factor 0.67 (such as attached drawing 4).
Embodiment 5: photosensitizer detects titanium dioxide photo anode retention of color
M2C6 synthesized by embodiment 1 (8.00mg) is dissolved in distilled water (14.5mL), is used under the monitoring of pH meter
The aqueous solution of nitric acid of 0.010M adjusts the pH to 3.8 of the aqueous solution of M2C6, and the concentration of photosensitizer is 0.50mmol/L at this time, will receive
Rice titanium dioxide photo anode immerses, and room temperature takes out after 2 hours, with distilled water flushing, after drying under the conditions of 80 DEG C, then with greatly
Measure distilled water flushing, without obvious decoloration, be assembled into battery behind efficiency compared with dye-sensitized solar cells obtained in embodiment 3 without
It is substantially reduced.
Claims (2)
1. application protection is cationic water-soluble bipyridyl-ruthenium class photosensitizer M2C6 structure, the structure of M2C6 with imidazoles
It is as shown in the figure:
2. application protection claim 1 in M2C6 preparation method, the preparation method is as follows: (1) by 522.4mg bromo 3- just oneself
Base -1,2- methylimidazole is dissolved in 1mL methanol, and 117.8mg potassium hydroxide is separately dissolved in methanol, and the methanol of potassium hydroxide is molten
Drop adds the methanol solution of bromo 3- n-hexyl -1,2- methylimidazole, stirs 12 hours, must clarify at room temperature after suction filtration
Solution, filtered solution methanol dilution to 8mL are configured to the n-hexyl of 3- containing hydroxide -1,2- methylimidazole concentration
For the methanol solution of 0.25mmol/mL；(2) by the bis- (2,2'- bipyridyl -4,4'- two of 211.7mg cis--bis- (isothiocyano)
Carboxyl) ruthenium (II) is dissolved in 5mL methanol, hydroxide 3- n-hexyl -1,2- methylimidazole obtained in step (1) is added
The methanol solution 4.8mL of 0.25mmol/mL is added 20mL ether and solid is precipitated, filtered with Buchner funnel after stirring at normal temperature 1 hour
Solid 310mg is obtained afterwards, solid is dissolved in 10mL methanol, and the nitric acid methanol solution that 4.3mL concentration is 0.1mol/L is added, is concentrated into
2mL, is added 10mL ether, and solid is precipitated, filters and be dried in vacuo, obtain 153.6mg black solid M2C6, yield: 48%.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1359901A (en) * | 2000-12-21 | 2002-07-24 | 中国科学院感光化学研究所 | Ru-polypyridine complex and its synthesizing process and use |
| CN102617647A (en) * | 2012-02-28 | 2012-08-01 | 中山大学 | Terpyridyl ruthenium coordination compound, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1359901A (en) * | 2000-12-21 | 2002-07-24 | 中国科学院感光化学研究所 | Ru-polypyridine complex and its synthesizing process and use |
| CN102617647A (en) * | 2012-02-28 | 2012-08-01 | 中山大学 | Terpyridyl ruthenium coordination compound, and preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| Combined Experimental and DFT-TDDFT Computational Study of Photoelectrochemical Cell Ruthenium Sensitizers;Mohammad K. Nazeeruddin et al.;《J. AM. CHEM. SOC.》;20051231;第127卷;第16835-16847页 |
| Md. K. Nazeeruddin et al..Acid-Base Equilibria of (2,2¢-Bipyridyl-4,4¢-dicarboxylic acid)ruthenium(II) Complexes and the Effect of Protonation on Charge-Transfer Sensitization of Nanocrystalline Titania.《Inorg. Chem.》.1999,第38卷 |
| N-杂环卡宾-吡啶基钌光敏染料结构与性能的理论研究;夏喜泉;《哈尔滨理工大学》;20140630;全文 |
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