Abstract
Zinc tetraphenylporphyrin (ZnTPP) was modified by a push-pull strategy and then density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were performed for the resulting derivatives. The smallest HOMO–LUMO energy gaps were found in ZnTPP-6 and ZnTPP-7, which had nitro substituents and a conjugated chain, while the largest was observed for ZnTPP-5. The energy gaps of all of the systems designed in this work were smaller than that of ZnTPP. Clear intramolecular charge transfer was observed from donor to acceptor in ZnTPP-6 and ZnTPP-7, which had nitro groups at positions R8, R9, and R10, as well as in ZnTPP-3 and ZnTPP-4, which had cyano groups at those positions. The narrow band gaps (compared to that of ZnTPP) of these designed systems, where the LUMO is above the conduction band of TiO2 and the HOMO is below the redox couple, indicate that they are efficient sensitizers. The B bands of these newly designed derivatives, except for ZnTPP-5, are redshifted compared with the B band of ZnTPP.
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References
O’Regan B, Gratzel M (1991) Nature 353:737–740
Nazeeruddin MK, Angelis FD, Fantacci S, Selloni A, Viscardi G, Liska P, Ito S, Takeru B, Gratzel M (2005) J Am Chem Soc 127:16835–16847
Wang Q, Campbell WM, Bonfantani EE, Jolley KW, Officer DL, Walsh PJ, Gordon K, Humphry-Baker R, Nazeeruddin MK, Gratzel M (2005) J Phys Chem B 109:15397–15409
Go Sun Solutions (2012) Website. http://gosunsolutions.com/home/content/view/46/2/
Bai Y, Cao YM, Zhang J, Wang MK, Li RZ, Wang P, Zakeeruddin SM, Gratzel M (2008) Nature Mat 7:626–630
Gao F, Wang Y, Shi D, Zhang J, Wang MK, Jing XY, Humphary-Baker R, Wang P, Zakeeruddin SM, Gratzel M (2008) J Am Chem Soc 130:10720–10728
Tsai HH, Simpson MC (2002) Chem Phys Lett 353:111–118
Walsh PJ, Gordon KC, Officer DL, Campbell WM (2006) J Mol Struct (THEOCHEM) 759:17–24
Cleland DM, Gordon KC, Officer DL, Wagner P, Walsh PJ (2009) Spectrochim Acta Part A 74:931–935
Duncan WR, Prezhdo OV (2007) Ann Rev Phys Chem 58:143–184
Claessens CG, Hahn U, Torres T (2008) Chem Rec 8:75–97
Milgrom LR (1997) The colours of life: an introduction to the chemistry of porphyrins and related compounds. Oxford University Press, Oxford
Choi M-S, Yamazaki T, Yamazaki I, Aida T (2004) Angew Chem Int Ed 43:150–158
Dong ZC, Guo XL, Wakayama Y, Hou JG (2006) Surf Rev Lett 13:143–147
Campbell WM, Jolley KW, Wagner P, Wagner K, Walsh PJ, Gordon KC, Schmidt-Mende L, Nazeeruddin MK, Wang Q, Graetzel M, Officer DL (2007) J Phys Chem C 111:11760–11762
Xiang N, Zhou W, Jiang S, Deng L, Liu Y, Tan Z, Zhao B, Shen P, Tan S (2011) Sol Energy Mater Sol Cells 95:1174–1181
Angelis FD, Fntacci S, Selloni A (2008) Nanotechnology 19:424002
Ito S, Zakeeruddin SM, Humphry-Baker R, Liska P, Charvet R, Comte P, Nazeeruddin MK, Péchy P, Takata M, Miura H, Uchida S, Grätzel M (2006) Adv Mater 18:1202–1205
Gouterman M (1978) In: Dolphin D (ed) The porphyrins, vol 3. Academic, New York, pp 1–153
Smith KM (1972) Porphyrins and metalloporphyrins. Elsevier, Amsterdam
Strachan JP, Gentemann S, Seth J, Kalsbeck WA, Lindsey JS, Holten D, Bocian DF (1997) J Am Chem Soc 119:11191–11201
Yang SI, Seth J, Balasubramanian T, Kim D, Lindsey JS, Holten D, Bocian DF (1999) J Am Chem Soc 121:4008–4018
Frisch MJ et al (2009) Gaussian 09, revision A.1. Gaussian Inc., Wallingford
Bhattacharjee CR, Das G, Purkayastha DD, Kanoo P, Mondal P (2011) J Coord Chem 64:2746–2760
Tsai FC, Chang CC, Liu CL, Chen WC, Jenekhe SA (2005) Macromolecules 38:1958–1966
Cao H, Ma J, Zhang G, Jiang Y (2005) Macromolecules 38:1123–1130
Hutchison GR, Ratner MA, Marks TJ (2005) J Phys Chem B 109:3126–3138
Hutchison GR, Ratner MA, Marks TJ (2005) J Am Chem Soc 127:2339–2350
Salzner U, Lagowski JB, Pickup PG, Poirier RA (1998) Synth Met 96:177–189
Salzner U (2001) Synth Met 119:215–216
Delley B (2000) J Chem Phys 113:7756–7764
Wu J, Hagelberg F (2011) J Phys Chem C 115:4571–4577
Barone V, Hod O, Peralta JE, Scuseria GE (2011) Acc Chem Res 44:269–279
Irfan A, Cui R, Zhang J, Nadeem M (2010) Aust J Chem 63:1–7
Irfan A, Nadeem M, Athar M, Kanwal F, Zhang J (2011) Comput Theor Chem 968:8–11
Irfan A, Al-Sehemi AG, Asiri AM (2012) J Mol Model. doi:10.1007/s00894-012-1372-9
Irfan A, Al-Sehemi AG, Asiri AM, Nadeem M, Alamry KA (2011) Comput Theor Chem 977:9–12
Wan L, Zhang YX, Qi DD, Jiang JH (2010) J Mol Graphics Modell 28:842–851
Liu ZQ, Chen ZX, Jin BB, Zhang XX (2011) Vib Spectr 56:210–218
Li L, Tang Q, Li H, Yang X, Hu W, Song Y, Shuai Z, Xu W, Liu Y, Zhu D (2007) Adv Mater 19:2613–2617
Irfan A, Zhang J, Chang Y (2009) Chem Phys Lett 483:143–146
Ma R, Guo P, Yang L, Guo L, Zeng Q, Liu G, Zhang X (2010) J Mol Struct (THEOCHEM) 942:131–136
Byrn MP, Curtis CJ, Goldberg I, Hsiou Y, Khan SI, Sawin PA, Tendick SK, Strouse CE (1991) J Am Chem Soc 113:6549–6557
Nemykin VN, Basu P (2001) Virtual molecular orbital description program (VMOdes). Department of Chemistry, Duquesne University, Pittsburgh
Scheidt WR, Kastner ME, Hatano K (1978) Inorg Chem 17:706–710
Golder AJ, Povey DC (1990) Acta Crystallogr C 46:1210–1212
Balanay MP, Kim DH (2008) Phys Chem Chem Phys 10:5121–5127
Aihara JI (1999) J Phys Chem A 103:7487–7495
Kaur I, Jia W, Kopreski RP, Selvarasah S, Dokmeci MR, Pramanik C, McGruer NE, Miller GP (2008) J Am Chem Soc 130:16274–16286
De Oliveira MA, Duarte HA, Pernaut J-M, De Almeida WB (2000) J Phys Chem A 104:8256–8262
do Couto PC, Guedes RC, Cabral BJC (2004) Braz J Phys 34:42–47
Irfan A, Cui RH, Zhang JP, Hao LZ (2009) Chem Phys 364:39–45
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We are thankful to King Khalid University for its support and for providing the facilities needed to carry out the research work.
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Irfan, A., Hina, N., Al-Sehemi, A.G. et al. Quantum chemical investigations aimed at modeling highly efficient zinc porphyrin dye sensitized solar cells. J Mol Model 18, 4199–4207 (2012). https://doi.org/10.1007/s00894-012-1421-4
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DOI: https://doi.org/10.1007/s00894-012-1421-4