Abstract
Density functional theory (DFT) and time-dependent DFT (TD-DFT) methodologies have been applied in an attempt to improve the performance of the dye YD2-o-C8 which is characterized by 11.9–12.7 % efficiencies. We aimed at narrowing the band gap of YD2-o-C8 to extend the light harvesting region to near IR. This was done through replacing the porphyrin macrocycle by the tetraazaporphyrin (porphyrazin) macrocycle, so that the performances of the suggested cells could be improved with Ti38O76, (TiO2)60, SiC, ZrO2, and GaP semiconductor electrodes. The effects of modifying the central macrocycle on cell performance are confirmed in terms of FMOs, energy gaps, electrode (VB and CB) edges, density of states (DOS), MEPs, dipole moments, IP, EA, reorganization energies, UV–Vis absorption, ΦLHE, Φinjection, and life times of the excited states. Replacing porphyrin macrocycle by porphyrazin macrocycle resulted in charge separated states, unidirectional charge transfer, narrower band gaps, increase of DOS nearby Fermi levels, asymmetric polarization, delocalization of the negative charges near the anchoring groups, efficient electron injection, suppressing macrocycle aggregation, active dye regeneration, longer life times of the excited states, and inhibited dye recombination. Co-sensitizers are suggested for near IR sensitization to improve the photo-to-current conversion efficiency. Size ranges: for dyes (0.1–1 nm), and for pore diameters of a dye sensitized mesoporous film of TiO2 (2–50 nm).
Similar content being viewed by others
References
Balanay MP, Kim DH (2009) Structures and excitation energies of Zn–tetraarylporphyrin analogues: a theoretical study. J Mol Struct 910:20–26
Barbara PF, Meyer TJ, Ratner MA (1996) Contemporary issues in electron transfer research. J Phys Chem 100:13148–13168
Becke AD (1988) Density–functional exchange–energy approximation with correct asymptotic behavior. Phys Rev A 38:3098–3100
Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5653
Caballol R, Castell O, Illas F, Malrieu JP, Moreira IPR (1997) Remarks on the proper use of the broken symmetry approach to magnetic coupling. J Phys Chem A 101:7860–7866
Cahen D, Hodes G, Gratzel M, Juillemoles JF, Riess I (2000) Nature of photovoltaic action in dye-sensitized solar cells. J Phys Chem B 104:2053–2059
Chen SL, Yang LN, Li ZS (2013) How to design more efficient organic dyes for dye sensitized solar cells? Adding more sp2-hybridized nitrogen in the triphenylamine donor. J Power Sources 223:86–93
Ditchfield R (1972) Molecular orbital theory of magnetic shielding and magnetic susceptibility. J Chem Phys 56(1972):5688–5692
Dong H, Zhou X, Jiang C (2012) Molecular design and theoretical investigation on novel porphyrin derivatives for dye-sensitized solar cells. Theor Chem Acc 131:1102–1113
Duncan WR, Stier W, Prezhdo OV (2007) Ab initio simulations of photoinduced molecule–semiconductor electron transfer, chap. 11. In: Balbuena PB, Seminario JM (eds) Nanomaterials: design and simulation. Elsevier BV, Amsterdam
Einstein A (1917) On the quantum theory of radiation. Phys Z 18:121–128
Frisch MJ et al (2010) Gaussian 98. Gaussian Inc., Pittsburgh
García-Iglesias M, Cid JJ, Yum JH, Forneli A, Vázquez P, Nazeeruddin MK, Palomares E, Grätzel M, Torres T (2011) Increasing the efficiency of zinc-phthalocyanine based solar cells through modification of the anchoring ligand. Energy Environ Sci 4:189–194
Gouterman M (1961) Spectra of porphyrins. J Mol Spectrosc 6:138–163
Gratzel M (2001) Review article. Photoelectrochemical cells. Nature 414(2001):338–344
Haque SA, Tachibana Y, Willis RL, Moser JE, Grätzel M, Klug DR, Durrant JR (2000) Parameters influencing charge recombination kinetics in dye-sensitized nanocrystalline titanium dioxide films. J Phys Chem B 104:538–547
Hara K, Wang ZS, Sato T, Furube A, Katoh R, Sugihara H, Dan-oh Y, Kasada C, Shinpo A, Suga S (2005) Oligothiophene-containing coumarin dyes for efficient dye-sensitized solar cells. J Phys Chem B 109:15476–15482
Hardin BE, Snaith HJ, McGehee MD (2012) The renaissance of dye-sensitized solar cells. Nat Photon 6:162–169
Horiuchi T, Miura H, Sumioka K, Uchida S (2004) High efficiency of dye-sensitized solar cells based on metal-free indoline dyes. J Am Chem Soc 126:12218–12219
Hutchison GR, Ratner MA, Marks TJ (2005) Hopping transport in conductive heterocyclic oligomers: reorganization energies and substituent effects. J Am Chem Soc 127:2339–2350
Jing D, Guo L, Zhao L, Zhang X, Liu H, Li M, Shen S, Liu G, Hu X, Zhang X, Zhang K, Ma L, Guo P (2010) Efficient solar hydrogen production by photocatalytic water splitting: from fundamental study to pilot demonstration. Int J Hydrogen Energy 35:7087–7097
Katoh R, Furube A, Yoshihara T, Hara K, Fujihashi G, Takano S, Murata S, Arakawa H, Tachiya M (2004) Efficiencies of electron injection from excited N3 dye into nanocrystalline semiconductor (ZrO2, TiO2, ZnO, Nb2O5, SnO2, In2O3) films. J Phys Chem B 108:4818–4822
Kose ME, Mitchell WJ, Kopidakis N, Chang CH, Shaheen SE, Kim K, Rumbles G (2007) Theoretical studies on conjugated phenyl-cored thiophene dendrimers for photovoltaic applications. J Am Chem Soc 129:14257–14270
Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789
Lee MJ, Balanay MP, Kim DH (2012) Molecular design of distorted push–pull porphyrins for dye-sensitized solar cells. Theor Chem Acc 131:1269
Lundqvist MJ, Nilsing M, Persson P, Luell S (2006) DFT study of bare and dye-sensitized TiO2 clusters and nanocrystals. Int J Quantum Chem 106:3214–3234
Marques MAL, Gross EKU (2004) Time-dependent density functional theory. Annu Rev Phys Chem 55:427–455
Moser JE, Gratzel M (1993) Observation of temperature independent heterogeneous electron transfer reactions in the inverted Marcus region. Chem Phys 176:493–500
Naray-Szabo G, Ferenczy GG (1995) Molecular electrostatics. Chem Rev 95:829–847
Nazeeruddin MK, Angelis FD, Fantacci S, Selloni A, Viscardi G, Liska P, Ito S, Takeru B, Gratzel M (2005) Combined experimental and DFT–TDDFT computational study of photoelectrochemical cell ruthenium sensitizers. J Am Chem Soc 127:16835–16847
Ning Z, Zhang Q, Pei H, Luan J, Lu C, Cui Y, Tian H (2009) Photovoltage improvement for dye-sensitized solar cells via cone-shaped structural design. J Phys Chem C 113:10307–10313
O’Boyle NM, Tenderholt AL, Langner KM (2008) cclib: a library for package-independent computational chemistry algorithms. J Comput Chem 29:839–845
Philaga K, Kleinpeter E (1994) Carbon-13 chemical in structural and stereochemical analysis. VCH Publishers, Deerfield Beach
Prasad O, Sinha L, Misra N, Narayan V, Kumar N, Pathak J (2010) Molecular structure and vibrational study on 2,3-dihydro-1H-indene and its derivative 1H-indene-1,3(2H)-dione by density functional theory calculations. J Mol Struct 940:82–86
Preat J, Michaux C, Jacquemin D, Perpète EA (2009) Enhanced efficiency of organic dye-sensitized solar cells: triphenylamine derivatives. J Phys Chem C 113:16821–16833
Preat J, Jacquemin D, Michaux C, Perpète EA (2010) Improvement of the efficiency of thiophene-bridged compounds for dye-sensitized solar cells. Chem Phys 376:56–68
Ragoussi ME, Cid JJ, Yum JH, Torre G, Censo DD, Grätzel M, Nazeeruddin MK, Torres T (2012) Carboxyethynyl anchoring ligands: a means to improving the efficiency of phthalocyanine-sensitized solar cells. Angew Chem 51:4375–4378
Retsek JL, Drain CM, Kirmaier C, Nurco DJ, Medforth J, Smith KM, Sazanovich IV, Chirvony VS, Fajer J, Holten D (2003) Photoinduced axial ligation and deligation dynamics of nonplanar nickel dodecaarylporphyrins. J Am Chem Soc 125:9787–9800
Senge MO, Fazekas M, Notaras EGA, Blau WJ, Zawadzka M, Locos OB, Mhuircheartaigh EMN (2007) Nonlinear optical properties of porphyrins. Adv Mater 19:2737–2774
Shalabi AS, El Mahdy AM, Assem MM, Taha HO, Abdel Halim WS (2013) Theoretical characterization of highly efficient dye sensitized solar cells. Mol Phys. http://dx.doi.org/10.1080/00268976.2013.795249
Tachinaba Y, Haque SA, Mercer IP, Durrant JR, Klug D (2000) Electron injection and recombination in dye sensitized nanocrystalline titanium dioxide films: a comparison of ruthenium bipyridyl and porphyrin sensitizer dyes. J Phys Chem B 104:1198–1205
Vosko SH, Wilk L, Nusair M (1980) Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can J Phys 58:1200–1211
Wang DL, Shen HT, Gu HM, Zhai YC (2006) Ab initio studies on the molecular electrostatic potential of C50. J Mol Struct 776:47–51
Wang J, Bai FQ, Xia BH, Feng L, Zhang HX, Pan QJ (2011) On the viability of cyclometalated Ru(II) complexes as dyes in DSSC regulated by COOH group, a DFT study. Chem Phys Phys Chem 13:2206–2213
Waston DF, Meyer GJ (2005) Electron injection at dye-sensitized semiconductor electrodes. Annu Rev Phys Chem 56:119–156
Wolinski K, Hinton JF, Pulay P (1990) Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J Am Chem Soc 112:8251–8260
Yang LN, Sun ZZ, Chen SL, Li ZS (2013) The effects of various anchoring groups on optical and electronic properties of dyes in dye-sensitized solar cells. Dyes Pigm 99:29–35
Yella A, Lee HW, Tsao HN, Yi C, Chandiran AK, Nazeeruddin MK, Diau EWG, Yeh CY, Zakeeruddin SM, Gratzel M (2011) Porphyrin-sensitized solar cells with cobalt (II/III)-based redox electrolyte exceed 12 percent efficiency. Science 334:629–634
Yum JH, Hagberg DP, Moon SJ, Karlsson KM, Marinado T, Sun L, Hagfeldt A, Nazeeruddin MK, Grätzel M (2009) A light-resistant organic sensitizer for solar-cell applications. Angew Chem 121:1604–1608
Zhang R, Du B, Sun G, Sun Y (2010) Experimental and theoretical studies on o-, m- and p-chlorobenzylideneaminoantipyrines. Spectrochim Acta A 75:1115–1124
Zhang S, Yang X, Numata Y, Han L (2013) Highly efficient dye-sensitized solar cells: progress and future challenges. Energy Environ Sci 6:1443–1464
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shalabi, A.S., El Mahdy, A.M., Assem, M.M. et al. Theoretical characterization of highly efficient porphyrazin dye sensitized solar cells. J Nanopart Res 16, 2579 (2014). https://doi.org/10.1007/s11051-014-2579-8
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s11051-014-2579-8