染料敏化太阳电池中N-环戊二烯基染料分子的理论研究（英文）
|
摘要
染料敏化太阳电池的一个重要的研究方向就是设计高效低成本的染料分子,文中,我们采用改性的苯基N-环戊二烯(PNP)作为供体端,理论设计了一系列高效的染料分子。根据已有的染料分子M5,本文首先设计了新的供体端,与M5相比,Z1N2染料分子的供体端由两个氨基分别连接苯基和PNP单元构成,吸收光谱明显红移。接着以Z1N2为模型,对分子进行进一步改进。在分子的受体端,在氰基丙烯酸的临位或对位,分别增加1-4个F离子。计算结果显示,F2-3分子的吸收光谱得到明显的改善。
One of the most significant aspects in the development of dye-sensitized solar cells(DSSCs) is to design high-efficiency and low-cost dyes. In this paper, we have reported the theoretical design of a series of potentially high-efficiency organic dyes with modified phenyl functionalized N-annulated perylene(PNP) donors, using density functional theory(DFT) and time-dependent density functional theory(TD-DFT) methods. In comparison with the model dye(M5), the designed Z1N2 dye with two amino groups connecting neighboring phenyl groups of PNP displays remarkably enhanced spectral responses in the visible light region. With Z1N2 as a prototype, further structural modifications were simulated by adding one, two, three or four fluorine atoms in the ortho or meta position of the cyanoacrylic acid moiety to make it a better acceptor unit. It is found that the modified dye F2-3 shows a much lower HOMO-LUMO energy gap and a significantly improved spectral response. Furthermore, the F2-3 dye possesses a larger vertical dipole moment than Z1N2. Based on the results of this study, the Z1N2 dye containing one fluorine atom in the ortho position and a cyanoacetic acid in the meta position. The modified molecule is expected to be a suitable dye for DSSC applications. The present findings are expected to provide an efficient route for the design and development of dyes with improved DSSC functionality.
One of the most significant aspects in the development of dye-sensitized solar cells(DSSCs) is to design high-efficiency and low-cost dyes. In this paper, we have reported the theoretical design of a series of potentially high-efficiency organic dyes with modified phenyl functionalized N-annulated perylene(PNP) donors, using density functional theory(DFT) and time-dependent density functional theory(TD-DFT) methods. In comparison with the model dye(M5), the designed Z1N2 dye with two amino groups connecting neighboring phenyl groups of PNP displays remarkably enhanced spectral responses in the visible light region. With Z1N2 as a prototype, further structural modifications were simulated by adding one, two, three or four fluorine atoms in the ortho or meta position of the cyanoacrylic acid moiety to make it a better acceptor unit. It is found that the modified dye F2-3 shows a much lower HOMO-LUMO energy gap and a significantly improved spectral response. Furthermore, the F2-3 dye possesses a larger vertical dipole moment than Z1N2. Based on the results of this study, the Z1N2 dye containing one fluorine atom in the ortho position and a cyanoacetic acid in the meta position. The modified molecule is expected to be a suitable dye for DSSC applications. The present findings are expected to provide an efficient route for the design and development of dyes with improved DSSC functionality.
引文
1 O'Regan B,Gr?tzel M.High-efficiency solar cell based on dye-sensitized colloidal Ti O2 films[J].Nature,1991,353(6346):737-740.
2 Capobianco A,Velardo A,and Peluso A.DFT predictions of the oxidation potential of organic dyes for opto-electronic devices[J].Computational&Theoretical Chemistry,2015,1070(15):68-75.
3 Mahmood A,Hussian M,Ahmad Irfan T,Al-Sehem A G.Heterocyclic azo dyes for dye sensitized solar cells:A quantum chemical study[J].Computational&Theoretical Chemistry,2015,1066(15):94-99.
4 Hao L,Wang J,Bai F Q,Xie M,Zhang H X.Theoretical studies of fluorine substituent effect on organic photosensitizers in dye sensitized solar calls[J].Computational&Theoretical Chemistry,2015,1067(1):119-128.
5 Fu J J,Duan Y A,Zhang J Z,Guo M S.Theoretical investigation of novel phenothiazine-based D-π-A conjugated organic dyes as dye-sensitizer in dye-sensitized solar cells[J].Computational&Theoretical Chemistry,2014,1045(1):145-153.
6 Zhang S,Islam A,Yang X,Qin C,Zhang K,Numata Y,Chen H,Han L.Improvement of spectral response by co-sensitizers for high efficiency dye-sensitized solar cells[J].Journal of Materials Chemistry A,2013,1(15):4812.
7 Kuang D,Walter P,Nuesch F,Kim S,Ko J,Comte P,Zakeeruddin S M,Nazeeruddin M K,Gr?tzel M.Cosensitization of organic dyes for efficient ionic liquid electrolyte-based dye-sensitized solar cells[J].Langmuir 2007,23(22):10906-10909.
8 Gr?tzel M.Recent advances in sensitized mesoscopic solar cells[J].Accounts of Chemical Research,2009,42(11):1788-1798.
9 L Gao F,Wang Y,Shi D.Enhance the optical absorptivity of nanocrystalline Ti O2 film with high molar extinction coefficient ruthenium sensitizers for high performance dyesensitized solar cells[J].Journal of the American Chemical Society,2008,130(32):10720-10728.
10 Cao Y,Bai Y,Yu Q,Cheng Y,Liu S,Shi D.Dye-sensitized solar cells with a high absorptivity ruthenium sensitizer featuring a 2-(Hexylthio)thiophene conjugated bipyridine[J].The Journal of Physical Chemistry C,2009,113(15):6290-6297.
11 Reynal A,Forneli A,Palomares E.Dye structure-charge transfer process relationship in efficient ruthenium-dye based dye sensitized solar cells[J].Energy&Environmental Science,2010,3(6):805.
12 Yella A,Lee H W,Tsao H N,Yi C,Chandiran A K,Nazeeruddin M K,Diau E W,Yeh C Y,Zakeeruddin S M,and Gr?tzel M.Porphyrin-sensitized solar cells with cobalt(II/III)-based redox electrolyte exceed 12 percent efficiency[J].Science 2011,334(6056):629-634.
13 Campbell W M,Jolley K W,Wagner P,Wagner K,Walsh P J,Gordon K C,Schmidt-Mende L,Nazeeruddin M K,Wang Q,Gr?tzel M D,Officer L.Highly efficient porphyrin sensitizers for dye-sensitized solar cells[J].Journal of Physical Chemistry C,2007,111(32):11760-11762.
14 Pastore M,Mosconi E,De Angelis F,Gr?tzel M.AComputational Investigation of Organic Dyes for DyeSensitized Solar Cells:Benchmark,Strategies,and Open Issues[J].Journal of Physical Chemistry C,2010,114(15):7205-7212.
15 Chen J,Li K,Luo Y,Guo X,Li D,Deng M.A flexible carbon counter electrode for dye-sensitized solar cells[J].Carbon.2009,47(11):2704-2708.
16 Yang J,Ganesan P,Teuscher J,Moehl T,Kim Y J,Yi C,Comte P,Pei K,Holcombe T W,Nazeeruddin M K,Hua J,Zakeeruddin S M,Tian H,Gr?tzel M.Influence of the donor size in D-π-A organic dyes for dye-sensitized solar cells[J].Journal of the American Chemical Society,2014,136(15):5722-5730.
17 Tarsang R,Promarak V,Sudyoadsuk T,Namuangruk S,Jungsuttiwong S.Tuning the electron donating ability in the triphenylamine-based D-π-A architecture for highly efficient dye-sensitized solar cells[J].Journal of Photochemistry and Photobiology A,2014,273:8-16.
18 Tarsang R,Promarak V,Sudyoadsuk T,Namuangruk S,Kungwan N,Jungsuttiwong S.Modification of D-A-π-Aconfiguration toward a high-performance triphenylaminebased sensitizer for dye-sensitized solar cells:A theoretical investigation[J].Chemphyschem 2014,15(17):3809-3818.
19 Chen S L,Yang L N,Li Z S.How to design more efficient organic dyes for dye-sensitized solar cells?Adding more sp2-hybridized nitrogen in the triphenylamine donor[J].Journal of Power Sources,2013,223(1):86-93.
20 Zhang J,Yang L,Zhang M,Wang P.Theoretical investigation of the donor group related electronic structure properties in pushpull organic sensitizers[J].RSC Adv.2013,3(17):6030-6035.
21 Feng J,Jiao Y,Ma W,Nazeeruddin M K,Gr?tzel M,Meng S.First principles design of dye molecules with ullazinedonor for dye sensitized solar cells[J].The Journal of Physical Chemistry C,2013,117(8):3772-3778.
22 Ambrosio F,Martsinovich N,Troisi A.Effect of the anchoring group on electron injection:theoretical study of phosphonated dyes for dye-sensitized solar cells[J].The Journal of Physical Chemistry C,2012,116(3):2622-2629.
23 Ambrosio F,Martsinovich N,Troisi A.What is the best anchoring group for a dye in a dye-sensitized solar cell[J].The Journal of Physical Chemistry Letters,2012,3(11):1531-1535.
24 Yang L N,Sun Z Z,Chen S L,Li Z S.The effects of various anchoring groups on optical and electronic properties of dyes in dye-sensitized solar cells[J].Dyes and Pigments2013,99(1):29-35.
25 Lin L Y,Yeh M H,Lee C P,Chang J,Baheti A,Vittal R,Thomas K R J,Ho K C.Insights into the co-sensitizer adsorption kinetics for complementary organic dye-sensitized solar cells[J].Journal of Power Sources,2014,247(1):906-914.
26 Wurthner F.Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures[J].Chemical Communications,2004,14(21):1564-1579.
27 Wonneberger C,Li H.Perylene imides for organic photovoltaics:yesterday,today,and tomorrow[J].Advanced Materials,2012,24(5):613-636.
28 Ferrere S,Zaban A,Gregg B.A.Dye sensitization of nanocrystalline tin oxide by perylene derivatives[J].The Journal of Physical Chemistry B,1997,101(23):4490-4493.
29 Wang J,Wu H,Jin L,A Perylene-Based Polycyclic Aromatic Hydrocarbon Electron-Donor for a Highly Efficient Solar Cell Dye[J].Chemsuschem,2017,10(14):2962-2967.
30 Yan C,Ma W,Ren Y,Zhang M,Wang P.Efficient triarylamine perylene dye-sensitized solar cells:influence of triple-bond insertion on charge recombination[J].ACS Applied Materials&Interfaces,2015,7(1):801-809.
31 Yang L,Ren Y,Yao Z,Yan C,Ma W,Wang P.Electronacceptor-sependent light absorption and charge-transfer dynamics in N-annulated perylene dye-sensitized solar cells[J].The Journal of Physical Chemistry C,2015,119(2):980-988.
32 Qi Q,Wang X,Fan L,Zheng B,Zeng W,Luo J,Huang K W,Wang Q,Wu J.N-annulated perylene-based push-pull-type sensitizers[J].Organic Letters,2015,17(3):724-727.
33 Luo J,Xu M,Li R,Huang K W,Jiang C,Qi Q,Zeng W,Zhang J,Chi C,Wang P,Wu J.N-annulated perylene as an efficient electron donor for porphyrin-based dyes:enhanced lightharvesting ability and high-efficiency Co(II/III)-based dyesensitized solar cells[J].Journal of the American Chemical Society,2014,136(1):265-272.
34 Yao Z Y,Min Z,Wu H,Yang L,Li R Z,Wang P.A donoracceptor indenoperylene dye for highly efficient organic dyesensitized solar cells[J].Journal of the American Chemical Society,2015,vol.137(11):3799-3802.
35 Ahmad S,Guillen E,Kavan L,Gr?etzel M,Nazeeruddin M K.Metal free sensitizer and catalyst for dye sensitized solar cells[J].Energy&Environmental Science,2013,6(12):3439-3466.
36 Hara K,Sato T,Katoh R,Furube A,Ohga Y,Shinpo A,Suga S,Sayama K,Sugihara H,Arakawa H.Molecular design of coumarin dyes for efficient dye-sensitized solar cells[J].Journal of Physical Chemistry B,2003,107(2):597-606.
37 Zhu W,Wu Y,Wang S,Li W,Li X,Chen J,Wang Z S,Tian H.Organic D-A-π-A solar cell sensitizers with improved stability and spectral response[J].Advanced Functional Materials,2011,21(4):756-763.
38 Choi H,Baik C,Kang S O,Ko,Kang M S,Nazeeruddin M K,Gr?etzel M.Highly efficient and thermally stable organic sensitizers for solvent-free dye-sensitized solar cells[J].Angewandte Chemie,2009,121(10):1739-1739.
39 Tang J,Wu W,Hua J,Li J,Li X,Tian H.Starburst triphenylamine-based cyanine dye for efficient quasi-solidstate dye-sensitized solar cells[J].Energy&Environmental Science,2009,2(9):982-990.
40 Kim B G,Zhen C G,Jeong E J,Kieffer J J.Organic Dye Design Tools for Efficient Photocurrent Generation in DyeSensitized Solar Cells:Exciton Binding Energy and Electron Acceptors[J].Advanced Functional Materials,2012,22(8):1606-1612.
41 Kim B G,Chung K,Kim J.Molecular Design Principle of Allorganic Dyes for Dye-Sensitized Solar Cells[J].Chemistry-AEuropean Journal,2013,19(17):5220-5230.
42 Lee M W,Kim J Y,Son H J,Kim J Y,Kim B,Kim H,Lee DK,Kim K,Lee D H,Ko M J.Tailoring of Energy Levels in D-π-A Organic Dyes via Fluorination of Acceptor Units for Efficient Dye-Sensitized Solar Cells[J].Scientific Reports,2015,5:7711.
43 Chou H-H,Yang C-H,Lin J T,Hsu C-P.First-Principle Determination of Electronic Coupling and Prediction of Charge Recombination Rates in Dye-Sensitized Solar Cells[J].The Journal of Physical Chemistry C,2017,121(2):983-992.
44 Zhang L,Liu X,Rao W,Li J.Multilayer Dye Aggregation at Dye/Ti O2 Interface viaπ…πStacking and Hydrogen Bond and Its Impact on Solar Cell Performance:A DFT Analysis[J].Scientific Reports,2016,6:35893.
45 Chitumalla R K,Jang J.Density functional theory study on ruthenium dyes and dye@TiO2 assemblies for dye sensitized solar cell applications[J].Soler Energy,2018,159:283-290.
46 Mendizabal F,Mera-Adasme R,Xu W-H,Sundholm D.Electronic and optical properties of metalloporphyrins of zinc on Ti O2 cluster in dye-sensitized solar-cells(DSSC).Aquantum chemistry study[J].RSC Advance.2017,7(68):42677-42684.
47 Li P,Wang Z,Song C,Zhang H.Rigid fusedπ-spacer in D-π-A type molecule for dyesensitized solar cell:A computational investigation[J].Journal of Materials Chemistry C,2017,5(44):11454-11465.
48 Amaya Suárez J,Plata J J,Márquez A M,Fernández Sanz J.Ag2S Quantum Dot-Sensitized Solar Cells by First Principles:The Effect of Capping Ligands and Linkers[J].The Journal of Physical Chemistry A,2017,121(38):7290-7296.
49 Lee G H,Kwon D Y,Kim Y S.Theoretical Study of Heteroleptic Dual Electron Acceptors for Dye-Sensitized Solar Cells Based on A-D-A Organic Dyes[J].Journal of Nanoscience&Nanotechnology,2016,16(8):8602-8606.
50 Delgado-Montiel T,Baldenebro-López J,Soto-Rojo R,Glossman-Mitnik D.Quantum chemical study of the effect ofπ-bridge on the optical and electronic properties of sensitizers for DSSCs incorporating dioxythiophene and thiophene units[J].Theoretical Chemistry Accounts,2016,135(10):235.
51 Liu H,Wang X,Pan C,et al.First-Principles Study of Formaldehyde Adsorption on TiO2 Rutile(110)and Anatase(001)Surfaces[J].Journal of Physical Chemistry C,2012,116(14):8044-8053.
52 Mara M W,Bowman D N,Buyukcakir O,Shelby M L,Haldrup K,Huang J.Electron Injection from Copper Diimine Sensitizers into TiO2:Structural Effects and Their Implications for Solar Energy Conversion Devices[J].Journal of the American Chemical Society,2015,137(30):9670-9684.
53 Zhang J,Zhang J-Z,Li H-B,Wu Y,Geng Y,Su Z-M.Rational modifications on champion porphyrin dye SM315 using different electron-withdrawing moieties toward high performance dye-sensitized solar cells[J].Phys.Chem.Chem.Phys.,2014,16(45):24994-5003.
54 Frisch M J,Trucks G W,Schlegel H B,Scuseria G E,Robb MA,Cheeseman J R,Scalmani G,Barone V,Mennucci B,Petersson G A,Nakatsuji H,Caricato M,Li X,Izmaylov A F,Bloino J,Zheng G,Sonnenberg J L,Hada M,Ehara M,Toyota K,Fukuda R,Hasegawa J,Ishida M,Nakajima T,Honda Y,Kitao O,Nakai,H,Vreven T,Montgomery J A,Peralta J E,Ogliaro F,Bearpark M,Heyd J J,Brothers E,Kudin K N,Staroverov V N,Kobayashi R,Normand J,Raghavachari K,Rendell A,Burant J C,Iyengar S S,Tomasi J,Cossi M,Rega N,Millam J M,Klene M,Knox J E,Cross J B,Bakken V,Adamo C,Jaramillo J,Gomperts R,Stratmann R E,Yazye v AO,Austin J,Cammi R,Pomelli C,Ochterski J W,Martin RL,Morokuma K,Zakrzewski V G,Voth G A,Salvador P,Dannenberg J J,Dapprich S,Daniels A D,Farkas O,Foresman J B,Ortiz J V,Cioslowski J,Fox D J.Gaussian 09,Revision D.01,Gaussian,Inc.,Wallingford CT,2009.
55 Becke A D.Density-functinonal thermochemistry.Ш.The role of exact exchange[J].Journal of Physical Chemistry,1993,98(7):5648-5652.
56 Becke A.D.A new mixing of hartree-fork and local densityfunctional theories[J].Journal of Physical Chemistry,1993,98:1372-1377.
57 Lee C T,Yang W T,Parr R G.Development of the ColleSalvetti correlation-energy formula into a functional of the electron density[J].Phys Rev B Condens Matter,1988,37(2):785-789.
58 Barone V,Cossi M.Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model[J].Journal of Physical Chemistry A,1998,102(11):1995-2001.
59 Cammi R,Mennucci B,Tomasi J.Second-order MollerPlesset analytical derivatives for the polarizable continuum model using the relaxed density approach[J].The Journal of Physical Chemistry A,1999,103(45):9100-9108.
60 Klamt A,Schuurmann G.Cosmo:a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient[J].Journal of the Chemical Society Perkin Transactions 2,1993,2(5):799-805.
61 Jacquemin D,Perpete E A,Scuseria G E,Ciofini I,Adamo C.TD-DFT Performance for the Visible Absorption Spectra of Organic Dyes:Conventional Versus Long-Range Hybrids[J].Journsl of Chemical Theory and Computation,2007,4(1):123-135.
62 Becke A D.Density-Functional Thermochemistry.III.The Role of Exact Exchange[J].Journal of Chemical Physics,1993,98(7):5648-5652.
63 Yanai T,Tew D P,Handy N C.A new hybrid exchangecorrelation functional using the Coulomb-attenuating method(CAM-B3LYP)[J].Chemical Physics Letters,2004,393(1-3):51-57.
64 Multiwfn,Lu T.Version 3.3.7,A Multifunctional Wavefunction Analyzer.
65 Marinado T,Hagberg D P,Hedlund M,Edvinsson T,Johansson E M J,Boschloo G,Rensmo H,Brinck T,Sun L.How the nature of triphenylamine-polyene dyes in dye-sensitized solar cells affects the open-circuit voltage and electron lifetimes[J].Phys Chem Chem Phys,2009,11(1):133-141.
66 Zhang J,Li H B,Zhang J Z,Wu Y,Geng Y,Fu Q,Su Z M.Apromising anchor group for efficient organic dye sensitized solar cells with iodine-free redox shuttles:a theoretical evaluation[J].Journal of Materials Chemistry A,2013,1(44):14000-14007.
67 Marinado T,Nonomura K,Nissfolk J,Karlsson M K,Hagberg D P,Sun L,Mori S,Hagfeldt A.How the nature of triphenylamine-polyene dyes in dye-sensitized solar cells affects the open-circuit voltage and electron lifetimes[J].Langmuir 2010,26(4):2592-2598.
68 Lu X,Wei S,Wu C M L,Li S,Guo W.Can polypyridyl Cu(?)-based complexes provide promising sensitizers for dyesensitized solar cells?A theoretical insight into Cu(?)versus Ru(II)sensitizers[J].Journal of Physical Chemistry C,2011,115(9):3753-3761.
69 Zhang J,Li H B,Sun S L,Geng Y,Wu Y,Su Z M.Density functional theory characterization and design of highperformance diarylamine-fluorene dyes with different pi spacers for dye-sensitized solar cells[J].Journal of Materials Chemistry,2011,22.
70 Rühle S,Greenshtein M,Chen S G,Merson A,Pizem H,Sukenik C S,Cahen D,Zaban A.Molecular Adjustment of the Electronic Properties of Nanoporous Electrodes in DyeSensitized Solar Cells[J].Journal of Physical Chemistry B,2005,109(40):18907-18913.
71 Einstein A.On the quantum theory of radiation[J].Concepts of Quantum Optics,1983,59(2):93-104.
72 Preat J,Jacquemin D,Perpete E A.Towards new efficient dyesensitised solar cells[J].Eeergy&&Environmental Science,2010,3(7):891-904.
73 De Angelis F,Fantacci S,Selloni A,Gr?etzel M,Nazeeruddin,M.K.Influence of the sensitizer adsorption mode on the opencircuit potential of dye-sensitized solar cells[J].Nano Letters.2007,7(10):3189-3195.
74 Chen P,Yum J H,De Angelis F E,Mosconi S,Fantacci S J,Baker R H,Ko J,Nazeeruddin M K,Gr?etzel M.High OpenCircuit Voltage Solid-State Dye-Sensitized Solar Cells with Organic Dye[J].Nano Letters.2009,9(6):2487-2492.
75 Kim J Y,Kim J Y,Lee D K,Kim B,Kim H,Ko M J.Importance of 4-tert-Butylpyridine in Electrolyte for DyeSensitized Solar Cells Employing Sn O2 Electrode[J].The Journal of Physical Chemistry C,2012,116(43):22759-22766.
76 Biswas A K,Barik S,Sen A,Das A,Ganguly B.Design of efficient metal-free organic dyes having an azacyclazine scaffold as the donor fragment for dye-sensitized solar calls[J].Journal of Physical Chemistry C,2014,118(36):20763-20771.
2 Capobianco A,Velardo A,and Peluso A.DFT predictions of the oxidation potential of organic dyes for opto-electronic devices[J].Computational&Theoretical Chemistry,2015,1070(15):68-75.
3 Mahmood A,Hussian M,Ahmad Irfan T,Al-Sehem A G.Heterocyclic azo dyes for dye sensitized solar cells:A quantum chemical study[J].Computational&Theoretical Chemistry,2015,1066(15):94-99.
4 Hao L,Wang J,Bai F Q,Xie M,Zhang H X.Theoretical studies of fluorine substituent effect on organic photosensitizers in dye sensitized solar calls[J].Computational&Theoretical Chemistry,2015,1067(1):119-128.
5 Fu J J,Duan Y A,Zhang J Z,Guo M S.Theoretical investigation of novel phenothiazine-based D-π-A conjugated organic dyes as dye-sensitizer in dye-sensitized solar cells[J].Computational&Theoretical Chemistry,2014,1045(1):145-153.
6 Zhang S,Islam A,Yang X,Qin C,Zhang K,Numata Y,Chen H,Han L.Improvement of spectral response by co-sensitizers for high efficiency dye-sensitized solar cells[J].Journal of Materials Chemistry A,2013,1(15):4812.
7 Kuang D,Walter P,Nuesch F,Kim S,Ko J,Comte P,Zakeeruddin S M,Nazeeruddin M K,Gr?tzel M.Cosensitization of organic dyes for efficient ionic liquid electrolyte-based dye-sensitized solar cells[J].Langmuir 2007,23(22):10906-10909.
8 Gr?tzel M.Recent advances in sensitized mesoscopic solar cells[J].Accounts of Chemical Research,2009,42(11):1788-1798.
9 L Gao F,Wang Y,Shi D.Enhance the optical absorptivity of nanocrystalline Ti O2 film with high molar extinction coefficient ruthenium sensitizers for high performance dyesensitized solar cells[J].Journal of the American Chemical Society,2008,130(32):10720-10728.
10 Cao Y,Bai Y,Yu Q,Cheng Y,Liu S,Shi D.Dye-sensitized solar cells with a high absorptivity ruthenium sensitizer featuring a 2-(Hexylthio)thiophene conjugated bipyridine[J].The Journal of Physical Chemistry C,2009,113(15):6290-6297.
11 Reynal A,Forneli A,Palomares E.Dye structure-charge transfer process relationship in efficient ruthenium-dye based dye sensitized solar cells[J].Energy&Environmental Science,2010,3(6):805.
12 Yella A,Lee H W,Tsao H N,Yi C,Chandiran A K,Nazeeruddin M K,Diau E W,Yeh C Y,Zakeeruddin S M,and Gr?tzel M.Porphyrin-sensitized solar cells with cobalt(II/III)-based redox electrolyte exceed 12 percent efficiency[J].Science 2011,334(6056):629-634.
13 Campbell W M,Jolley K W,Wagner P,Wagner K,Walsh P J,Gordon K C,Schmidt-Mende L,Nazeeruddin M K,Wang Q,Gr?tzel M D,Officer L.Highly efficient porphyrin sensitizers for dye-sensitized solar cells[J].Journal of Physical Chemistry C,2007,111(32):11760-11762.
14 Pastore M,Mosconi E,De Angelis F,Gr?tzel M.AComputational Investigation of Organic Dyes for DyeSensitized Solar Cells:Benchmark,Strategies,and Open Issues[J].Journal of Physical Chemistry C,2010,114(15):7205-7212.
15 Chen J,Li K,Luo Y,Guo X,Li D,Deng M.A flexible carbon counter electrode for dye-sensitized solar cells[J].Carbon.2009,47(11):2704-2708.
16 Yang J,Ganesan P,Teuscher J,Moehl T,Kim Y J,Yi C,Comte P,Pei K,Holcombe T W,Nazeeruddin M K,Hua J,Zakeeruddin S M,Tian H,Gr?tzel M.Influence of the donor size in D-π-A organic dyes for dye-sensitized solar cells[J].Journal of the American Chemical Society,2014,136(15):5722-5730.
17 Tarsang R,Promarak V,Sudyoadsuk T,Namuangruk S,Jungsuttiwong S.Tuning the electron donating ability in the triphenylamine-based D-π-A architecture for highly efficient dye-sensitized solar cells[J].Journal of Photochemistry and Photobiology A,2014,273:8-16.
18 Tarsang R,Promarak V,Sudyoadsuk T,Namuangruk S,Kungwan N,Jungsuttiwong S.Modification of D-A-π-Aconfiguration toward a high-performance triphenylaminebased sensitizer for dye-sensitized solar cells:A theoretical investigation[J].Chemphyschem 2014,15(17):3809-3818.
19 Chen S L,Yang L N,Li Z S.How to design more efficient organic dyes for dye-sensitized solar cells?Adding more sp2-hybridized nitrogen in the triphenylamine donor[J].Journal of Power Sources,2013,223(1):86-93.
20 Zhang J,Yang L,Zhang M,Wang P.Theoretical investigation of the donor group related electronic structure properties in pushpull organic sensitizers[J].RSC Adv.2013,3(17):6030-6035.
21 Feng J,Jiao Y,Ma W,Nazeeruddin M K,Gr?tzel M,Meng S.First principles design of dye molecules with ullazinedonor for dye sensitized solar cells[J].The Journal of Physical Chemistry C,2013,117(8):3772-3778.
22 Ambrosio F,Martsinovich N,Troisi A.Effect of the anchoring group on electron injection:theoretical study of phosphonated dyes for dye-sensitized solar cells[J].The Journal of Physical Chemistry C,2012,116(3):2622-2629.
23 Ambrosio F,Martsinovich N,Troisi A.What is the best anchoring group for a dye in a dye-sensitized solar cell[J].The Journal of Physical Chemistry Letters,2012,3(11):1531-1535.
24 Yang L N,Sun Z Z,Chen S L,Li Z S.The effects of various anchoring groups on optical and electronic properties of dyes in dye-sensitized solar cells[J].Dyes and Pigments2013,99(1):29-35.
25 Lin L Y,Yeh M H,Lee C P,Chang J,Baheti A,Vittal R,Thomas K R J,Ho K C.Insights into the co-sensitizer adsorption kinetics for complementary organic dye-sensitized solar cells[J].Journal of Power Sources,2014,247(1):906-914.
26 Wurthner F.Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures[J].Chemical Communications,2004,14(21):1564-1579.
27 Wonneberger C,Li H.Perylene imides for organic photovoltaics:yesterday,today,and tomorrow[J].Advanced Materials,2012,24(5):613-636.
28 Ferrere S,Zaban A,Gregg B.A.Dye sensitization of nanocrystalline tin oxide by perylene derivatives[J].The Journal of Physical Chemistry B,1997,101(23):4490-4493.
29 Wang J,Wu H,Jin L,A Perylene-Based Polycyclic Aromatic Hydrocarbon Electron-Donor for a Highly Efficient Solar Cell Dye[J].Chemsuschem,2017,10(14):2962-2967.
30 Yan C,Ma W,Ren Y,Zhang M,Wang P.Efficient triarylamine perylene dye-sensitized solar cells:influence of triple-bond insertion on charge recombination[J].ACS Applied Materials&Interfaces,2015,7(1):801-809.
31 Yang L,Ren Y,Yao Z,Yan C,Ma W,Wang P.Electronacceptor-sependent light absorption and charge-transfer dynamics in N-annulated perylene dye-sensitized solar cells[J].The Journal of Physical Chemistry C,2015,119(2):980-988.
32 Qi Q,Wang X,Fan L,Zheng B,Zeng W,Luo J,Huang K W,Wang Q,Wu J.N-annulated perylene-based push-pull-type sensitizers[J].Organic Letters,2015,17(3):724-727.
33 Luo J,Xu M,Li R,Huang K W,Jiang C,Qi Q,Zeng W,Zhang J,Chi C,Wang P,Wu J.N-annulated perylene as an efficient electron donor for porphyrin-based dyes:enhanced lightharvesting ability and high-efficiency Co(II/III)-based dyesensitized solar cells[J].Journal of the American Chemical Society,2014,136(1):265-272.
34 Yao Z Y,Min Z,Wu H,Yang L,Li R Z,Wang P.A donoracceptor indenoperylene dye for highly efficient organic dyesensitized solar cells[J].Journal of the American Chemical Society,2015,vol.137(11):3799-3802.
35 Ahmad S,Guillen E,Kavan L,Gr?etzel M,Nazeeruddin M K.Metal free sensitizer and catalyst for dye sensitized solar cells[J].Energy&Environmental Science,2013,6(12):3439-3466.
36 Hara K,Sato T,Katoh R,Furube A,Ohga Y,Shinpo A,Suga S,Sayama K,Sugihara H,Arakawa H.Molecular design of coumarin dyes for efficient dye-sensitized solar cells[J].Journal of Physical Chemistry B,2003,107(2):597-606.
37 Zhu W,Wu Y,Wang S,Li W,Li X,Chen J,Wang Z S,Tian H.Organic D-A-π-A solar cell sensitizers with improved stability and spectral response[J].Advanced Functional Materials,2011,21(4):756-763.
38 Choi H,Baik C,Kang S O,Ko,Kang M S,Nazeeruddin M K,Gr?etzel M.Highly efficient and thermally stable organic sensitizers for solvent-free dye-sensitized solar cells[J].Angewandte Chemie,2009,121(10):1739-1739.
39 Tang J,Wu W,Hua J,Li J,Li X,Tian H.Starburst triphenylamine-based cyanine dye for efficient quasi-solidstate dye-sensitized solar cells[J].Energy&Environmental Science,2009,2(9):982-990.
40 Kim B G,Zhen C G,Jeong E J,Kieffer J J.Organic Dye Design Tools for Efficient Photocurrent Generation in DyeSensitized Solar Cells:Exciton Binding Energy and Electron Acceptors[J].Advanced Functional Materials,2012,22(8):1606-1612.
41 Kim B G,Chung K,Kim J.Molecular Design Principle of Allorganic Dyes for Dye-Sensitized Solar Cells[J].Chemistry-AEuropean Journal,2013,19(17):5220-5230.
42 Lee M W,Kim J Y,Son H J,Kim J Y,Kim B,Kim H,Lee DK,Kim K,Lee D H,Ko M J.Tailoring of Energy Levels in D-π-A Organic Dyes via Fluorination of Acceptor Units for Efficient Dye-Sensitized Solar Cells[J].Scientific Reports,2015,5:7711.
43 Chou H-H,Yang C-H,Lin J T,Hsu C-P.First-Principle Determination of Electronic Coupling and Prediction of Charge Recombination Rates in Dye-Sensitized Solar Cells[J].The Journal of Physical Chemistry C,2017,121(2):983-992.
44 Zhang L,Liu X,Rao W,Li J.Multilayer Dye Aggregation at Dye/Ti O2 Interface viaπ…πStacking and Hydrogen Bond and Its Impact on Solar Cell Performance:A DFT Analysis[J].Scientific Reports,2016,6:35893.
45 Chitumalla R K,Jang J.Density functional theory study on ruthenium dyes and dye@TiO2 assemblies for dye sensitized solar cell applications[J].Soler Energy,2018,159:283-290.
46 Mendizabal F,Mera-Adasme R,Xu W-H,Sundholm D.Electronic and optical properties of metalloporphyrins of zinc on Ti O2 cluster in dye-sensitized solar-cells(DSSC).Aquantum chemistry study[J].RSC Advance.2017,7(68):42677-42684.
47 Li P,Wang Z,Song C,Zhang H.Rigid fusedπ-spacer in D-π-A type molecule for dyesensitized solar cell:A computational investigation[J].Journal of Materials Chemistry C,2017,5(44):11454-11465.
48 Amaya Suárez J,Plata J J,Márquez A M,Fernández Sanz J.Ag2S Quantum Dot-Sensitized Solar Cells by First Principles:The Effect of Capping Ligands and Linkers[J].The Journal of Physical Chemistry A,2017,121(38):7290-7296.
49 Lee G H,Kwon D Y,Kim Y S.Theoretical Study of Heteroleptic Dual Electron Acceptors for Dye-Sensitized Solar Cells Based on A-D-A Organic Dyes[J].Journal of Nanoscience&Nanotechnology,2016,16(8):8602-8606.
50 Delgado-Montiel T,Baldenebro-López J,Soto-Rojo R,Glossman-Mitnik D.Quantum chemical study of the effect ofπ-bridge on the optical and electronic properties of sensitizers for DSSCs incorporating dioxythiophene and thiophene units[J].Theoretical Chemistry Accounts,2016,135(10):235.
51 Liu H,Wang X,Pan C,et al.First-Principles Study of Formaldehyde Adsorption on TiO2 Rutile(110)and Anatase(001)Surfaces[J].Journal of Physical Chemistry C,2012,116(14):8044-8053.
52 Mara M W,Bowman D N,Buyukcakir O,Shelby M L,Haldrup K,Huang J.Electron Injection from Copper Diimine Sensitizers into TiO2:Structural Effects and Their Implications for Solar Energy Conversion Devices[J].Journal of the American Chemical Society,2015,137(30):9670-9684.
53 Zhang J,Zhang J-Z,Li H-B,Wu Y,Geng Y,Su Z-M.Rational modifications on champion porphyrin dye SM315 using different electron-withdrawing moieties toward high performance dye-sensitized solar cells[J].Phys.Chem.Chem.Phys.,2014,16(45):24994-5003.
54 Frisch M J,Trucks G W,Schlegel H B,Scuseria G E,Robb MA,Cheeseman J R,Scalmani G,Barone V,Mennucci B,Petersson G A,Nakatsuji H,Caricato M,Li X,Izmaylov A F,Bloino J,Zheng G,Sonnenberg J L,Hada M,Ehara M,Toyota K,Fukuda R,Hasegawa J,Ishida M,Nakajima T,Honda Y,Kitao O,Nakai,H,Vreven T,Montgomery J A,Peralta J E,Ogliaro F,Bearpark M,Heyd J J,Brothers E,Kudin K N,Staroverov V N,Kobayashi R,Normand J,Raghavachari K,Rendell A,Burant J C,Iyengar S S,Tomasi J,Cossi M,Rega N,Millam J M,Klene M,Knox J E,Cross J B,Bakken V,Adamo C,Jaramillo J,Gomperts R,Stratmann R E,Yazye v AO,Austin J,Cammi R,Pomelli C,Ochterski J W,Martin RL,Morokuma K,Zakrzewski V G,Voth G A,Salvador P,Dannenberg J J,Dapprich S,Daniels A D,Farkas O,Foresman J B,Ortiz J V,Cioslowski J,Fox D J.Gaussian 09,Revision D.01,Gaussian,Inc.,Wallingford CT,2009.
55 Becke A D.Density-functinonal thermochemistry.Ш.The role of exact exchange[J].Journal of Physical Chemistry,1993,98(7):5648-5652.
56 Becke A.D.A new mixing of hartree-fork and local densityfunctional theories[J].Journal of Physical Chemistry,1993,98:1372-1377.
57 Lee C T,Yang W T,Parr R G.Development of the ColleSalvetti correlation-energy formula into a functional of the electron density[J].Phys Rev B Condens Matter,1988,37(2):785-789.
58 Barone V,Cossi M.Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model[J].Journal of Physical Chemistry A,1998,102(11):1995-2001.
59 Cammi R,Mennucci B,Tomasi J.Second-order MollerPlesset analytical derivatives for the polarizable continuum model using the relaxed density approach[J].The Journal of Physical Chemistry A,1999,103(45):9100-9108.
60 Klamt A,Schuurmann G.Cosmo:a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient[J].Journal of the Chemical Society Perkin Transactions 2,1993,2(5):799-805.
61 Jacquemin D,Perpete E A,Scuseria G E,Ciofini I,Adamo C.TD-DFT Performance for the Visible Absorption Spectra of Organic Dyes:Conventional Versus Long-Range Hybrids[J].Journsl of Chemical Theory and Computation,2007,4(1):123-135.
62 Becke A D.Density-Functional Thermochemistry.III.The Role of Exact Exchange[J].Journal of Chemical Physics,1993,98(7):5648-5652.
63 Yanai T,Tew D P,Handy N C.A new hybrid exchangecorrelation functional using the Coulomb-attenuating method(CAM-B3LYP)[J].Chemical Physics Letters,2004,393(1-3):51-57.
64 Multiwfn,Lu T.Version 3.3.7,A Multifunctional Wavefunction Analyzer.
65 Marinado T,Hagberg D P,Hedlund M,Edvinsson T,Johansson E M J,Boschloo G,Rensmo H,Brinck T,Sun L.How the nature of triphenylamine-polyene dyes in dye-sensitized solar cells affects the open-circuit voltage and electron lifetimes[J].Phys Chem Chem Phys,2009,11(1):133-141.
66 Zhang J,Li H B,Zhang J Z,Wu Y,Geng Y,Fu Q,Su Z M.Apromising anchor group for efficient organic dye sensitized solar cells with iodine-free redox shuttles:a theoretical evaluation[J].Journal of Materials Chemistry A,2013,1(44):14000-14007.
67 Marinado T,Nonomura K,Nissfolk J,Karlsson M K,Hagberg D P,Sun L,Mori S,Hagfeldt A.How the nature of triphenylamine-polyene dyes in dye-sensitized solar cells affects the open-circuit voltage and electron lifetimes[J].Langmuir 2010,26(4):2592-2598.
68 Lu X,Wei S,Wu C M L,Li S,Guo W.Can polypyridyl Cu(?)-based complexes provide promising sensitizers for dyesensitized solar cells?A theoretical insight into Cu(?)versus Ru(II)sensitizers[J].Journal of Physical Chemistry C,2011,115(9):3753-3761.
69 Zhang J,Li H B,Sun S L,Geng Y,Wu Y,Su Z M.Density functional theory characterization and design of highperformance diarylamine-fluorene dyes with different pi spacers for dye-sensitized solar cells[J].Journal of Materials Chemistry,2011,22.
70 Rühle S,Greenshtein M,Chen S G,Merson A,Pizem H,Sukenik C S,Cahen D,Zaban A.Molecular Adjustment of the Electronic Properties of Nanoporous Electrodes in DyeSensitized Solar Cells[J].Journal of Physical Chemistry B,2005,109(40):18907-18913.
71 Einstein A.On the quantum theory of radiation[J].Concepts of Quantum Optics,1983,59(2):93-104.
72 Preat J,Jacquemin D,Perpete E A.Towards new efficient dyesensitised solar cells[J].Eeergy&&Environmental Science,2010,3(7):891-904.
73 De Angelis F,Fantacci S,Selloni A,Gr?etzel M,Nazeeruddin,M.K.Influence of the sensitizer adsorption mode on the opencircuit potential of dye-sensitized solar cells[J].Nano Letters.2007,7(10):3189-3195.
74 Chen P,Yum J H,De Angelis F E,Mosconi S,Fantacci S J,Baker R H,Ko J,Nazeeruddin M K,Gr?etzel M.High OpenCircuit Voltage Solid-State Dye-Sensitized Solar Cells with Organic Dye[J].Nano Letters.2009,9(6):2487-2492.
75 Kim J Y,Kim J Y,Lee D K,Kim B,Kim H,Ko M J.Importance of 4-tert-Butylpyridine in Electrolyte for DyeSensitized Solar Cells Employing Sn O2 Electrode[J].The Journal of Physical Chemistry C,2012,116(43):22759-22766.
76 Biswas A K,Barik S,Sen A,Das A,Ganguly B.Design of efficient metal-free organic dyes having an azacyclazine scaffold as the donor fragment for dye-sensitized solar calls[J].Journal of Physical Chemistry C,2014,118(36):20763-20771.