Theoretical study of Acene-bridged dyes for dye-sensitized solar cells

Journal of Physical Chemistry A

Volumn 119, Issue 13, 2015, Pages 3299-3309

  Li, Minjie ^a   Kou, Li ^a   Diao, Ling ^a   Zhang, Qing ^a   Li, Zhonggao ^a   Wu, Qiang ^a   Lu, Wencong ^a   Pan, Dengyu ^b  

^a College of Science   (China)

^b SHANGHAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTRA; ADSORPTION; DESIGN FOR TESTABILITY; DYE-SENSITIZED SOLAR CELLS; ELECTROMAGNETIC WAVE ABSORPTION; ELECTRONIC STRUCTURE; MOLECULAR ORBITALS; OPTICAL PROPERTIES; SOLAR CELLS; TITANIUM DIOXIDE;

ABSORPTION WAVELENGTHS; ADSORPTION ENERGIES; CONJUGATED BRIDGES; HIGHEST OCCUPIED MOLECULAR ORBITAL; OPTOELECTRONIC PROPERTIES; PHOTOPHYSICAL PROPERTIES; THEORETICAL STUDY; TIME DEPENDENT DENSITY FUNCTIONAL THEORY;

DENSITY FUNCTIONAL THEORY;

EID: 84926462522     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/acs.jpca.5b00798     Document Type: Article

References (58)

1. 2 Films Nature 1991, 353, 737-740
2. Gratzel, M. Photoelectrochemical Cells Nature 2001, 414, 338-344
3. Urbani, M.; Grätzel, M.; Nazeeruddin, M. K.; Torres, T. Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells Chem. Rev. 2014, 114, 12330-12396
4. Günes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated Polymer-Based Organic Solar Cells Chem. Rev. 2007, 107, 1324-1338
5. Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Dye-Sensitized Solar Cells Chem. Rev. 2010, 110, 6595-6663
6. Yasuo, C.; Ashraful, I.; Yuki, W.; Ryoichi, K.; Naoki, K.; Liyuan, H. Dye-Sensitized Solar Cells with Conversion Efficiency of 11.1% Jpn. J. Appl. Phys. 2006, 45, L638-L640
7. Nazeeruddin, M. K.; Bessho, T.; Cevey, L.; Ito, S.; Klein, C.; De Angelis, F.; Fantacci, S.; Comte, P.; Liska, P.; Imai, H. A High Molar Extinction Coefficient Charge Transfer Sensitizer and Its Application in Dye-Sensitized Solar Cell J. Photochem. Photobiol., A 2007, 185, 331-337
8. 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.; Gratzel, M. Porphyrin-Sensitized Solar Cells with Cobalt (II/III)-Based Redox Electrolyte Exceed 12% Efficiency Science 2011, 334, 629-634
9. Gregg, B. A. Evolution of Photophysical and Photovoltaic Properties of Perylene Bis(Phenethylimide) Films Upon Solvent Vapor Annealing J. Phys. Chem. 1996, 100, 852-859
10. Raavi, S. S. K.; Docampo, P.; Wehrenfennig, C.; Alcocer, M. J. P.; Sadoughi, G.; Herz, L. M.; Snaith, H. J.; Petrozza, A. Impact of Molecular Charge-Transfer States on Photocurrent Generation in Solid State Dye-Sensitized Solar Cells Employing Low-Band-Gap Dyes J. Phys. Chem. C 2014, 118, 16825-16830
11. Hara, K.; Kurashige, M.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Suga, S.; Sayama, K.; Arakawa, H. Design of New Coumarin Dyes Having Thiophene Moieties for Highly Efficient Organic-Dye-Sensitized Solar Cells New J. Chem. 2003, 27, 783-785
12. Zhong, C.; Gao, J.; Cui, Y.; Li, T.; Han, L. Coumarin-Bearing Triarylamine Sensitizers with High Molar Extinction Coefficient for Dye-Sensitized Solar Cells J. Power Sources 2015, 273, 831-838
13. Horiuchi, T.; Miura, H.; Sumioka, K.; Uchida, S. High Efficiency of Dye-Sensitized Solar Cells Based on Metal-Free Indoline Dyes J. Am. Chem. Soc. 2004, 126, 12218-12219
14. Venkateswararao, A.; Tyagi, P.; Thomas, K. R. J.; Chen, P.-W.; Ho, K.-C. Organic Dyes Containing Indolo 2,3-B Quinoxaline as a Donor: Synthesis, Optical and Photovoltaic Properties Tetrahedron 2014, 70, 6318-6327
15. 2 Film J. Phys. Chem. B 2002, 106, 1363-1371
16. Kim, D.; Lee, J. K.; Kang, S. O.; Ko, J. Molecular Engineering of Organic Dyes Containing N-Aryl Carbazole Moiety for Solar Cell Tetrahedron 2007, 63, 1913-1922
17. Liu, J.; Sun, X.; Li, Z.; Jin, B.; Lai, G.; Li, H.; Wang, C.; Shen, Y.; Hua, J. New D-Pi-a System Dye Based on Dithienosilole and Carbazole: Synthesis, Photo-Electrochemical Properties and Dye-Sensitized Solar Cell Performance J. Photochem. Photobiol., A 2014, 294, 54-61
18. Mao, M.; Zhang, X.-L.; Fang, X.-Q.; Wu, G.-H.; Dai, S.-Y.; Song, Q.-H.; Zhang, X.-X. Highly Efficient Light-Harvesting Boradiazaindacene Sensitizers for Dye-Sensitized Solar Cells Featuring Phenothiazine Donor Antenna J. Power Sources 2014, 268, 965-976
19. Matsui, M.; Mase, H.; Jin, J.-Y.; Funabiki, K.; Yoshida, T.; Minoura, H. Application of Semisquaric Acids as Sensitizers for Zinc Oxide Solar Cell Dyes Pigm. 2006, 70, 48-53
20. Lamberti, A.; Bella, F.; Sacco, A.; Bianco, S.; Tresso, E. Tio2 Nanotubes as Flexible Photoanode for Back-Illuminated Dye-Sensitized Solar Cells with Hemi-Squaraine Organic Dye and Iodine-Free Transparent Electrolyte Org. Electron. 2014, 15, 3715-3722
21. Kim, S.; Lee, J. K.; Kang, S. O.; Ko, J.; Yum, J. H.; Fantacci, S.; De Angelis, F.; Di Censo, D.; Nazeeruddin, M. K.; Grätzel, M. Molecular Engineering of Organic Sensitizers for Solar Cell Applications J. Am. Chem. Soc. 2006, 128, 16701-16707
22. Wee, K.-R.; Brennaman, M. K.; Alibabaei, L.; Farnum, B. H.; Sherman, B.; Lapides, A. M.; Meyer, T. J. Stabilization of Ruthenium(Ii) Polypyridyl Chromophores on Nanoparticle Metal-Oxide Electrodes in Water by Hydrophobic Pmma Overlayers J. Am. Chem. Soc. 2014, 136, 13514-13517
23. Negre, C. F. A.; Young, K. J.; Oviedo, M. B.; Allen, L. J.; Sánchez, C. G.; Jarzembska, K. N.; Benedict, J. B.; Crabtree, R. H.; Coppens, P.; Brudvig, G. W. Photoelectrochemical Hole Injection Revealed in Polyoxotitanate Nanocrystals Functionalized with Organic Adsorbates J. Am. Chem. Soc. 2014, 136, 16420-16429
24. 2 Nanostructures: An Experimental and Computational Study J. Am. Chem. Soc. 2015, 137, 1520-1529
25. Browning, C.; Hudson, J. M.; Reinheimer, E. W.; Kuo, F.-L.; McDougald, R. N.; Rabaâ, H.; Pan, H.; Bacsa, J.; Wang, X.; Dunbar, K. R. Synthesis, Spectroscopic Properties, and Photoconductivity of Black Absorbers Consisting of Pt(Bipyridine)(Dithiolate) Charge Transfer Complexes in the Presence and Absence of Nitrofluorenone Acceptors J. Am. Chem. Soc. 2014, 136, 16185-16200
26. Teng, C.; Yang, X.; Yang, C.; Li, S.; Cheng, M.; Hagfeldt, A.; Sun, L. Molecular Design of Anthracene-Bridged Metal-Free Organic Dyes for Efficient Dye-Sensitized Solar Cells J. Phys. Chem. C 2010, 114, 9101-9110
27. Wang, C.-L.; Chang, Y.-C.; Lan, C.-M.; Lo, C.-F.; Wei-Guang Diau, E.; Lin, C.-Y. Enhanced Light Harvesting with [Small Pi]-Conjugated Cyclic Aromatic Hydrocarbons for Porphyrin-Sensitized Solar Cells Energy Environ. Sci. 2011, 4, 1788-1795
28. Lin, C.-Y.; Wang, Y.-C.; Hsu, S.-J.; Lo, C.-F.; Diau, E. W.-G. Preparation and Spectral, Electrochemical, and Photovoltaic Properties of Acene-Modified Zinc Porphyrins J. Phys. Chem. C 2009, 114, 687-693
29. Park, G. E.; Shin, J.; Lee, D. H.; Lee, T. W.; Shim, H.; Cho, M. J.; Pyo, S.; Choi, D. H. Acene-Containing Donor-Acceptor Conjugated Polymers: Correlation between the Structure of Donor Moiety, Charge Carrier Mobility, and Charge Transport Dynamics in Electronic Devices Macromolecules 2014, 47, 3747-3754
30. Back, J. Y.; Kim, Y.; An, T. K.; Kang, M. S.; Kwon, S.-K.; Park, C. E.; Kim, Y.-H. Synthesis and Electrical Properties of Novel Oligomer Semiconductors for Organic Field-Effect Transistors (Ofets): Asymmetrically End-Capped Acene-Heteroacene Conjugated Oligomers Dyes Pigm. 2015, 112, 220-226
31. Motoyama, T.; Sugii, S.; Ikeda, S.; Yamaguchi, Y.; Yamada, H.; Nakayama, K.-i. Bulk-Heterojunction Organic Photovoltaic Devices Fabricated Using Asymmetric Soluble Anthracene Core Photoprecursors Jpn. J. Appl. Phys. 2014, 53, 01AB02
32. 2 Anatase (101) Surface J. Phys. Chem. C 2009, 113, 20117-20126
33. Fan, W.; Tan, D.; Deng, W. Q. Acene-Modified Triphenylamine Dyes for Dye-Sensitized Solar Cells: A Computational Study ChemPhysChem 2012, 13, 2051-2060
34. Yeh-Yung Lin, R.; Lin, H.-W.; Yen, Y.-S.; Chang, C.-H.; Chou, H.-H.; Chen, P.-W.; Hsu, C.-Y.; Chen, Y.-C.; Lin, J. T.; Ho, K.-C. 2,6-Conjugated Anthracene Sensitizers for High-Performance Dye-Sensitized Solar Cells Energy Environ. Sci. 2013, 6, 2477-2486
35. Justin Thomas, K. R.; Singh, P.; Baheti, A.; Hsu, Y.-C.; Ho, K.-C.; Lin, J. T. s. Electro-Optical Properties of New Anthracene Based Organic Dyes for Dye-Sensitized Solar Cells Dyes Pigm. 2011, 91, 33-43
36. Li, H.; Yang, Y.; Hou, Y.; Tang, R.; Duan, T.; Chen, J.; Wang, H.; Han, H.; Peng, T.; Chen, X. Organic Sensitizers Featuring 9,10-Diaryl-Substituted Anthracene Unit ACS Sustain. Chem. Eng. 2014, 2, 1776-1784
37. Ito, K.; Suzuki, T.; Sakamoto, Y.; Kubota, D.; Inoue, Y.; Sato, F.; Tokito, S. Oligo(2,6-Anthrylene)S: Acene-Oligomer Approach for Organic Field-Effect Transistors Angew. Chem. 2003, 115, 1191-1194
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. Gaussian 09, Revision A.01; Gaussian, Inc.: Wallingford, CT, 2009.
39. Becke, A. D. Density-Functional Thermochemistry. Iii. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
40. Rassolov, V. A.; Ratner, M. A.; Pople, J. A.; Redfern, P. C.; Curtiss, L. A. 6-31g∗ Basis Set for Third-Row Atoms J. Comput. Chem. 2001, 22, 976-984
41. Preat, J.; Michaux, C.; Jacquemin, D.; Perpète, E. A. Enhanced Efficiency of Organic Dye-Sensitized Solar Cells: Triphenylamine Derivatives J. Phys. Chem. C 2009, 113, 16821-16833
42. Li, W.; Wang, J.; Chen, J.; Bai, F. Q.; Zhang, H. X. Theoretical Investigation of Triphenylamine-Based Sensitizers with Different Pi-Spacers for Dssc Spectrochim. Acta A 2014, 118, 1144-1151
43. Ordon, P.; Tachibana, A. Investigation of the Role of the C-Pcm Solvent Effect in Reactivity Indices J. Chem. Sci. 2005, 117, 583-589
44. Cossi, M.; Barone, V. Time-Dependent Density Functional Theory for Molecules in Liquid Solutions J. Chem. Phys. 2001, 115, 4708-4717
45. Wu, Y.; Marszalek, M.; Zakeeruddin, S. M.; Zhang, Q.; Tian, H.; Graetzel, M.; Zhu, W. High-Conversion-Efficiency Organic Dye-Sensitized Solar Cells: Molecular Engineering on D-a-Pi-a Featured Organic Indoline Dyes Energy Environ. Sci. 2012, 5, 8261-8272
46. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods without Adjustable Parameters: The Pbe0Model J. Chem. Phys. 1999, 110, 6158-6170
47. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. Adiabatic Connection for Kinetics J. Phys. Chem. A 2000, 104, 4811-4815
48. Becke, A. D. A New Mixing of Hartree-Fock and Local Density-Functional Theories J. Chem. Phys. 1993, 98, 1372-1377
49. Yanai, T.; Tew, D. P.; Handy, N. C. A New Hybrid Exchange-Correlation Functional Using the Coulomb-Attenuating Method (Cam-B3lyp) Chem. Phys. Lett. 2004, 393, 51-57
50. Lu, T.; Chen, F. Multiwfn: A Multifunctional Wavefunction Analyzer J. Comput. Chem. 2012, 33, 580-592
51. Lu, T. Multiwfn, A Multifunctional Wavefunction Analyzer, version 3.6; http://Multiwfn.Codeplex.Com.
52. 3- Electrolytes Chem. - Eur. J. 2010, 16, 13127-13138
53. Mizuseki, H.; Niimura, K.; Majumder, C.; Belosludov, R. V.; Farajian, A. A.; Kawazoe, Y.; Majumder, C. Theoretical Study of Donor-Spacer-Acceptor Structure Molecule for Stable Molecular Rectifier Mol. Cryst. Liq. Cryst. 2003, 406, 205-211
54. Fitri, A.; Benjelloun, A. T.; Benzakour, M.; McHarfi, M.; Hamidi, M.; Bouachrine, M. Theoretical Investigation of New Thiazolothiazole-Based D-Pi-a Organic Dyes for Efficient Dye-Sensitized Solar Cell Spectrochim. Acta, Part A 2014, 124, 646-654
55. Hodge, P.; A. Power, G.; A. Rabjohns, M. Synthesis of Poly(Anthracene-2,6-Diyl) and a Copolymer Containing Alternately Anthracene-2,6-Diyl and P-Phenylene Units Chem. Commun. 1997, 73-74
56. Müller, U.; Adam, M.; Müllen, K. Synthesis and Characterization of Soluble Oligo(9,10-Anthrylene)S Chem. Ber. 1994, 127, 437-444
57. Becker, H. D.; Langer, V.; Sieler, J.; Becker, H. C. Molecular Conformations of 9,9-Bianthryl, Di-9-Anthrylmethane, and Some Related Twisted Anthracene Derivatives J. Org. Chem. 1992, 57, 1883-1887
58. Delley, B. An All-Electron Numerical Method for Solving the Local Density Functional for Polyatomic Molecules J. Chem. Phys. 1990, 92, 508-517