Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Non-linear Optical Response of Triphenylamine Dyes with D-A-π-A Structure
Corresponding Author(s) : Asif Mahmood
Asian Journal of Chemistry,
Vol. 28 No. 9 (2016): Vol 28 Issue 9
Abstract
In this study, we have designed new triphenylamine dyes with D-A-π-A structure and calculated their electro-optical and non-linear properties. Computational techniques were used to study the effect of additional acceptor in π-conjugated systems on absorption spectra and non-linear properties. All the dyes show absorbance in visible region. During theoretical examination polarizability (α), hyperpolarizability (β) and electronic transitions were calculated. Results indicated that the selection of appropriate lengths of conjugated bridges in dye is very important to design high efficiency dyes. This theoretical frame work would be useful to design other organic dyes.
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- D.J. Williams, Angew. Chem. Int. Ed. Engl., 23, 690 (1984); doi:10.1002/anie.198406901.
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- N.J. Long, Angew. Chem. Int. Ed. Engl., 34, 21 (1995); doi:10.1002/anie.199500211.
- M. Stähelin, D.M. Burland and J.E. Rice, Chem. Phys. Lett., 191, 245 (1992); doi:10.1016/0009-2614(92)85295-L.
- S. Ramasesha and P.K. Das, Chem. Phys., 145, 343 (1990); doi:10.1016/0301-0104(90)87043-B.
- Y. Gong, Y. Tan, J. Liu, P. Lu, C. Feng, W.Z. Yuan, Y. Lu, J.Z. Sun, G. He and Y. Zhang, Chem. Commun., 49, 4009 (2013); doi:10.1039/c3cc39243k.
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- W. Li, Y. Wu, Q. Zhang, H. Tian and W. Zhu, ACS Appl. Mater. Interfaces, 4, 1822 (2012); doi:10.1021/am3001049.
- Y. Wu, X. Zhang, W. Li, Z.-S. Wang, H. Tian and W. Zhu, Adv. Energy Mater., 2, 149 (2012); doi:10.1002/aenm.201100341.
- S. Qu, C. Qin, A. Islam, Y. Wu, W. Zhu, J. Hua, H. Tian and L. Han, Chem. Commun., 48, 6972 (2012); doi:10.1039/c2cc31998e.
- M.J. Frisch et al., Gaussian 09, Gaussian, Inc. (2009).
- J. Autschbach, ChemPhysChem, 10, 1757 (2009); doi:10.1002/cphc.200900268.
- A. Dreuw and M. Head-Gordon, Chem. Rev., 105, 4009 (2005); doi:10.1021/cr0505627.
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- M. Pastore, E. Mosconi, F. De Angelis and M. Grätzel, J. Phys. Chem. C, 114, 7205 (2010); doi:10.1021/jp100713r.
- T. Yanai, D.P. Tew and N.C. Handy, Chem. Phys. Lett., 393, 51 (2004); doi:10.1016/j.cplett.2004.06.011.
- V. Barone and M. Cossi, J. Phys. Chem. A, 102, 1995 (1998); doi:10.1021/jp9716997.
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- H.S. Nalwa, Handbook of Advanced Electronic and Photonic Materials and Devices, Academic, San Diego, CA (2001).
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References
D.J. Williams, Angew. Chem. Int. Ed. Engl., 23, 690 (1984); doi:10.1002/anie.198406901.
A. Datta and S. Pal, J. Mol. Struct. THEOCHEM, 715, 59 (2005); doi:10.1016/j.theochem.2004.10.054.
A. Garza, O. Osman, N. Wazzan, S. Khan, A. Asiri and G. Scuseria, Theor. Chem. Acc., 133, 1458 (2014); doi:10.1007/s00214-014-1458-9.
S.A. Siddiqui, T. Rasheed, M. Faisal, A.K. Pandey and S.B. Khan, Spectrosc. Int. J., 27, 185 (2012); doi:10.1155/2012/614710.
R.-L. Zhong, S.-L. Sun, H.-L. Xu, Y.-Q. Qiu and Z.-M. Su, J. Phys. Chem. C, 118, 14185 (2014); doi:10.1021/jp503281q.
R.-L. Zhong, S.-L. Sun, H.-L. Xu, Y.-Q. Qiu and Z.-M. Su, ChemPlusChem., 79, 732 (2014); doi:10.1002/cplu.201300381.
M.R.S.A. Janjua, S. Jamil, T. Ahmad, Z. Yang, A. Mahmood and S. Pan, Comput. Theoret. Chem., 1033, 6 (2014); doi:10.1016/j.comptc.2014.01.031.
M.R.S.A. Janjua, S. Jamil, A. Mahmood, A. Zafar, M. Haroon and H.N. Bhatti, Aust. J. Chem., 68, 1502 (2015); doi:10.1071/CH14736.
M.R.S.A. Janjua, M.U. Khan, B. Bashir, M.A. Iqbal, Y. Song, S.A.R. Naqvi and Z.A. Khan, Computat. Theoret. Chem., 994, 34 (2012);doi:10.1016/j.comptc.2012.06.011.
M.R.S.A. Janjua, A. Mahmood and F. Ahmad, Can. J. Chem., 91, 1303 (2013); doi:10.1139/cjc-2013-0377.
Y. Zeng, Z.-H. Pan, F.-L. Zhao, M. Qin, Y. Zhou and C.-S. Wang, Chinese Phys. B, 23, 024212 (2014); doi:10.1088/1674-1056/23/2/024212.
N.J. Long, Angew. Chem. Int. Ed. Engl., 34, 21 (1995); doi:10.1002/anie.199500211.
M. Stähelin, D.M. Burland and J.E. Rice, Chem. Phys. Lett., 191, 245 (1992); doi:10.1016/0009-2614(92)85295-L.
S. Ramasesha and P.K. Das, Chem. Phys., 145, 343 (1990); doi:10.1016/0301-0104(90)87043-B.
Y. Gong, Y. Tan, J. Liu, P. Lu, C. Feng, W.Z. Yuan, Y. Lu, J.Z. Sun, G. He and Y. Zhang, Chem. Commun., 49, 4009 (2013); doi:10.1039/c3cc39243k.
X. Ma, X. Mao, S. Zhang, X. Huang, Y. Cheng and C. Zhu, Polymer Chem., 4, 520 (2013); doi:10.1039/C2PY20677C.
M. Marszalek, S. Nagane, A. Ichake, R. Humphry-Baker, V. Paul, S.M. Zakeeruddin and M. Gratzel, RSC Adv., 3, 7921 (2013); doi:10.1039/c3ra22249g.
Y. Ooyama, N. Yamaguchi, I. Imae, K. Komaguchi, J. Ohshita and Y. Harima, Chem. Commun., 49, 2548 (2013); doi:10.1039/c3cc40498f.
M.R.S.A. Janjua, Z.H. Yamani, S. Jamil, A. Mahmood, I. Ahmad, M. Haroon, M.H. Tahir, Z. Yang and S. Pan, Aust. J. Chem., 69, 467 (2016); doi:10.1071/CH15402.
W. Li, Y. Wu, Q. Zhang, H. Tian and W. Zhu, ACS Appl. Mater. Interfaces, 4, 1822 (2012); doi:10.1021/am3001049.
Y. Wu, X. Zhang, W. Li, Z.-S. Wang, H. Tian and W. Zhu, Adv. Energy Mater., 2, 149 (2012); doi:10.1002/aenm.201100341.
S. Qu, C. Qin, A. Islam, Y. Wu, W. Zhu, J. Hua, H. Tian and L. Han, Chem. Commun., 48, 6972 (2012); doi:10.1039/c2cc31998e.
M.J. Frisch et al., Gaussian 09, Gaussian, Inc. (2009).
J. Autschbach, ChemPhysChem, 10, 1757 (2009); doi:10.1002/cphc.200900268.
A. Dreuw and M. Head-Gordon, Chem. Rev., 105, 4009 (2005); doi:10.1021/cr0505627.
J. Preat, C. Michaux, D. Jacquemin and E.A. Perpète, J. Phys. Chem. C, 113, 16821 (2009); doi:10.1021/jp904946a.
S. Kim, J.K. Lee, S.O. Kang, J. Ko, J.-H. Yum, S. Fantacci, F. De Angelis, D. Di Censo, M.K. Nazeeruddin and M. Grätzel, J. Am. Chem. Soc., 128, 16701 (2006); doi:10.1021/ja066376f.
D. Jacquemin, V. Wathelet, E.A. Perpète and C. Adamo, J. Chem. Theory Comput., 5, 2420 (2009); doi:10.1021/ct900298e.
M. Pastore, E. Mosconi, F. De Angelis and M. Grätzel, J. Phys. Chem. C, 114, 7205 (2010); doi:10.1021/jp100713r.
T. Yanai, D.P. Tew and N.C. Handy, Chem. Phys. Lett., 393, 51 (2004); doi:10.1016/j.cplett.2004.06.011.
V. Barone and M. Cossi, J. Phys. Chem. A, 102, 1995 (1998); doi:10.1021/jp9716997.
A. Karakas, A. Elmali and H. Unver, Spectrochim. Acta A, 68, 567 (2007); doi:10.1016/j.saa.2006.12.029.
B.A.S. Mendis and K.M.N. de Silva, J. Mol. Struct. THEOCHEM, 678, 31 (2004); doi:10.1016/j.theochem.2004.02.027.
H.S. Nalwa, Handbook of Advanced Electronic and Photonic Materials and Devices, Academic, San Diego, CA (2001).
D.R. Kanis, M.A. Ratner and T.J. Marks, J. Am. Chem. Soc., 114, 10338 (1992); doi:10.1021/ja00052a035.