Theoretical study on the correlations between dye-iodine interactions and open-circuit voltages in dyes containing furan and thiophene

Computational and Theoretical Chemistry

Volumn 1029, Issue , 2014, Pages 1-12

  Balanay, Mannix P ^a   Kim, Dong Hee ^a  

^a Kunsan National University   (South Korea)

Author keywords

Charge recombination; Density functional theory; Dye sensitized solar cells; Iodide triiodide redox couple; Organic dyes

Indexed keywords

EID: 84891295731     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2013.12.005     Document Type: Article

References (50)

1. 2 films. Nature 1991, 353:737-740.
2. Grätzel M. Dye-sensitized solar cells. J. Photochem. Photobiol. C 2003, 4:145-153.
3. Grätzel M. Conversion of sunlight to electric power by nanocrystalline dye-sensitized solar cells. J. Photochem. Photobiol. A 2004, 164:3-14.
4. Hao F., Dong P., Luo Q., Li J., Lou J., Lin H. Recent advances in alternative cathode materials for iodine-free dye-sensitized solar cells. Energy Environ. Sci. 2013, 6:2003-2019.
5. Ondersma J.W., Hamann T.W. Recombination and redox couples in dye-sensitized solar cells. Coord. Chem. Rev. 2013, 257:1533-1543.
6. Wang M., Gratzel C., Zakeeruddin S.M., Gratzel M. Recent developments in redox electrolytes for dye-sensitized solar cells. Energy Environ. Sci. 2012, 5:9394-9405.
7. Clifford J.N., Palomares E., Nazeeruddin M.K., Grätzel M., Durrant J.R. Dye dependent regeneration dynamics in dye sensitized nanocrystalline solar cells: evidence for the formation of a ruthenium bipyridyl cation/iodide intermediate. J. Phys. Chem. C 2007, 111:6561-6567.
8. Boschloo G., Hagfeldt A. Characteristics of the iodide/triiodide redox mediator in dye-sensitized solar cells. Acc. Chem. Res. 2009, 42:1819-1826.
9. Gardner J.M., Giaimuccio J.M., Meyer G.J. Evidence for iodine atoms as intermediates in the dye sensitized formation of I-I bonds. J. Am. Chem. Soc. 2008, 130:17252-17253.
10. Asaduzzaman A.M., Chappellaz G.A.G., Schreckenbach G. Relationship between dye-iodine binding and cell voltage in dye-sensitized solar cells: a quantum-mechanical look. J. Comput. Chem. 2012, 33:2492-2497.
11. Asaduzzaman A.M., Schreckenbach G. Interactions of the N3 dye with the iodide redox shuttle: quantum chemical mechanistic studies of the dye regeneration in the dye-sensitized solar cell. Phys. Chem. Chem. Phys. 2011, 13:15148-15157.
12. Liu T., Troisi A. Theoretical evidence of multiple dye regeneration mechanisms in dye-sensitized solar cells. Chem. Phys. Lett. 2013, 570:159-162.
13. Anderson A.Y., Barnes P.R.F., Durrant J.R., O'Regan B.C. Quantifying regeneration in dye-sensitized solar cells. J. Phys. Chem. C 2011, 115:2439-2447.
14. Kusama H., Sugihara H., Sayama K. Theoretical study on the interactions between black dye and iodide in dye-sensitized solar cells. J. Phys. Chem. C 2011, 115:9267-9275.
15. 2. J. Phys. Chem. B 2000, 104:1791-1795.
16. Fitzmaurice D.J., Frei H. Transient near-infrared spectroscopy of visible light sensitized oxidation of iodide at colloidal titania. Langmuir 1991, 7:1129-1137.
17. Nyhlen J., Boschloo G., Hagfeldt A., Kloo L., Privalov T. Regeneration of oxidized organic photo-sensitizers in grätzel solar cells: quantum-chemical portrait of a general mechanism. ChemPhysChem 2010, 11:1858-1862.
18. Maggio E., Martsinovich N., Troisi A. Evaluating charge recombination rate in dye-sensitized solar cells from electronic structure calculations. J. Phys. Chem. C 2012, 116:7638-7649.
19. Miyashita M., Sunahara K., Nishikawa T., Uemura Y., Koumura N., Hara K., Mori A., Abe T., Suzuki E., Mori S. Interfacial electron-transfer kinetics in metal-free organic dye-sensitized solar cells: combined effects of molecular structure of dyes and electrolytes. J. Am. Chem. Soc. 2008, 130:17874-17881.
20. 2 sensitized solar cells. Energy Environ. Sci. 2011, 4:1820-1829.
21. Maggio E., Martsinovich N., Troisi A. Theoretical study of charge recombination at the TiO2-electrolyte interface in dye sensitised solar cells. J. Chem. Phys. 2012, 137.
22. 2 films. J. Phys. Chem. B 2005, 109:142-150.
23. Pastore M., Mosconi E., De Angelis F. Computational investigation of dye-iodine interactions in organic dye-sensitized solar cells. J. Phys. Chem. C 2012, 116:5965-5973.
24. Zhang M., Liu J., Wang Y., Zhou D., Wang P. Redox couple related influences of π-conjugation extension in organic dye-sensitized mesoscopic solar cells. Chem. Sci. 2011, 2:1401-1406.
25. Zhang J., Kan Y.-H., Li H.-B., Geng Y., Wu Y., Su Z.-M. How to design proper π-spacer order of the D-π-A dyes for DSSCs? A density functional response. Dyes Pigm. 2012, 95:313-321.
26. Giribabu L., Kanaparthi R.K., Velkannan V. Molecular engineering of sensitizers for dye-sensitized solar cell applications. Chem. Rec. 2012, 12:306-328.
27. Kanaparthi R.K., Kandhadi J., Giribabu L. Metal-free organic dyes for dye-sensitized solar cells: recent advances. Tetrahedron 2012, 68:8383-8393.
28. Yen Y.-S., Chou H.-H., Chen Y.-C., Hsu C.-Y., Lin J.T. Recent developments in molecule-based organic materials for dye-sensitized solar cells. J. Mater. Chem. 2012, 22:8734-8747.
29. Li R., Lv X., Shi D., Zhou D., Cheng Y., Zhang G., Wang P. Dye-sensitized solar cells based on organic sensitizers with different conjugated linkers: furan, bifuran, thiophene, bithiophene, selenophene, and biselenophene. J. Phys. Chem. C 2009, 113:7469-7479.
30. Kim S.H., Kim H.W., Sakong C., Namgoong J., Park S.W., Ko M.J., Lee C.H., Lee W.I., Kim J.P. Effect of five-membered heteroaromatic linkers to the performance of phenothiazine-based dye-sensitized solar cells. Org. Lett. 2011, 13:5784-5787.
31. O'Regan B.C., Walley K., Juozapavicius M., Anderson A., Matar F., Ghaddar T., Zakeeruddin S.M., Klein C.D., Durrant J.R. Structure/function relationships in dyes for solar energy conversion: a two-atom change in dye structure and the mechanism for its effect on cell voltage. J. Am. Chem. Soc. 2009, 131:3541-3548.
32. Balanay M.P., Kim D.H. Computational study of absorption energies of organic sensitizers used in photovoltaic applications. J. Phys. Chem. C 2011, 115:19424-19430.
33. Chudzinski M.G., Taylor M.S. Correlations between computation and experimental thermodynamics of halogen bonding. J. Org. Chem. 2012, 77:3483-3491.
34. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A.M. Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision B.01, Gaussian Inc, Wallingford, CT, 2010.
35. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98:5648.
36. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37:785-789.
37. Grimme S. Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J. Comput. Chem. 2006, 27:1787-1799.
38. Zhao Y., Truhlar D. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 2008, 120:215-241.
39. Adamo C., Barone V. Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters: The mPW and mPW1PW models. J. Chem. Phys. 1998, 108:664-675.
40. Perdew J.P., Burke K., Wang Y. Generalized gradient approximation for the exchange-correlation hole of a many-electron system. Phys. Rev. B 1996, 54:16533-16539.
41. Godbout N., Salahub D.R., Andzelm J., Wimmer E. Optimization of Gaussian-type basis sets for local spin density functional calculations. Part I. Boron through neon, optimization technique and validation. Can. J. Chem. 1992, 70:560-571.
42. Yurieva A.G., Poleshchuk O.K., Filimonov V.D. Comparative analysis of a full-electron basis set and pseudopotential for the iodine atom in DFT quantum-chemical calculations of iodine-containing compounds. J. Struct. Chem. 2008, 49:548-552.
43. Check C.E., Faust T.O., Bailey J.M., Wright B.J., Gilbert T.M., Sunderlin L.S. Addition of polarization and diffuse functions to the LANL2DZ basis set for P-Block elements. J. Phys. Chem. A 2001, 105:8111-8116.
44. Feller D. The role of databases in support of computational chemistry calculations. J. Comput. Chem. 1996, 17:1571-1586.
45. Schuchardt K.L., Didier B.T., Elsethagen T., Sun L., Gurumoorthi V., Chase J., Li J., Windus T.L. Basis set exchange: a community database for computational sciences. J. Chem. Inf. Model. 2007, 47:1045-1052.
46. Cossi M., Rega N., Scalmani G., Barone V. Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J. Comput. Chem. 2003, 24:669-681.
47. E.D. Glendening, J.K. Badenhoop, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO Version 3.1, Theoretical Chemistry Institute, University of Wisconsin, Madison, USA.
48. Lee M.J., Balanay M.P., Kim D.H. Molecular design of distorted push-pull porphyrins for dye-sensitized solar cells. Theor. Chem. Acc. 2012, 131:1269.
49. Balanay M.P., Kim S.M., Lee M.J., Lee S.H., Kim D.H. Conformational analysis and electronic properties of 2-cyano-3-(thiophen-2-yl) acrylic acid in sensitizers for dye-sensitized solar cells: a theoretical study. Bull. Korean Chem. Soc. 2009, 30:2077-2082.
50. Holliman P.J., Mohsen M., Connell A., Davies M.L., Al-Salihi K., Pitak M.B., Tizzard G.J., Coles S.J., Harrington R.W., Clegg W., Serpa C., Fontes O.H., Charbonneau C., Carnie M.J. Ultra-fast co-sensitization and tri-sensitization of dye-sensitized solar cells with N719, SQ1 and triarylamine dyes. J. Mater. Chem. 2012, 22:13318-13327.