Density Functional Theory Predictions of the Nonlinear Optical (NLO) Properties in Triphenylamine based α-Cyanocinnamic Acid Compounds: Effect of Fluorine on NLO Response

Authors

  • Muhammad Ramzan Saeed Ashraf Janjua Janjua King Fahd University of Petroleum and Minerals (KFUPM) Dhahran 31261 P.O Box 5048, Kingdom of Saudi Arabia

DOI:

https://doi.org/10.29356/jmcs.v62i3.551

Keywords:

DFT, Nonlinear Optics, Molecular modeling

Abstract

In this study, the energy gaps, second-order nonlinear optical (NLO) properties and dipole polarizabilities of triphenylamine based α-cyanocinnamic acid acetylene derivatives have been investigated via using time-dependent density functional response theory. These compounds were designed theoretically by fluorine (F) atom substitution at different positions of phenyl ring end of the α-cyanocinnamic acid segment. The results have indicated that the systems substituted by fluorine show remarkable NLO second-order response, especially D4 system with computed static second-order polarizability (βtot) of 70537.95 (a.u). Hence, these materials have the likelihood to be an excellent second-order nonlinear optical (NLO) materials. The βtot value suggests that along the x-axis the charge transfer (CT) from triphenylamine to α-cyanocinnamic acid (D-A) plays a key role in NLO response; whereas α-cyanocinnamic acid acts as an acceptor (A) and triphenylamine acts as a donor (D) in all the studied systems. Incorporation of an electron acceptor (F) at the phenyl ring end of the α-cyanocinnamic acid segment increases the computed βtot values. The present investigation therefore provides an important insight into the remarkably greater NLO properties of α-cyanocinnamic acid and triphenylamine attached via acetylene.

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Author Biography

Muhammad Ramzan Saeed Ashraf Janjua Janjua, King Fahd University of Petroleum and Minerals (KFUPM) Dhahran 31261 P.O Box 5048, Kingdom of Saudi Arabia

Dr. Muhammad Ramzan Saeed Ashraf Janjua is currently serving as Assistant Professor at KFUPM (Chemistry Department). He earned his Ph.D. (Physical Chemistry) in 2010 from NENU, China. His research was based on the computational modeling of functional, inorganic-organic hybrid materials which stand out for their remarkable nonlinear optical properties. In 2010, he joined University of Sargodha, Pakistan as Assistant Professor (Currently on Ex-Pakistan Extra-Ordinary Leave) and in the meantime he completed his one year Post-Doc (2011-2012) from University of Coimbra Portugal. He is a Visiting Research Scientist at Chinese Academy of Sciences since 2014. He has also won the Best Research Paper Award by HEC, Pakistan for the year 2012 (M.R.S.A. Janjua, Inorg. Chem. 51 (2012), 11306-11314). He is an author of more than 40 publications printed in world's leading scientific societies e.g., ACS, RSC, Wiley, and Elsevier. 

References

J.P. Costes, J.F. Lamere, C. Lepetit, P.G. Lacroix, F. Dahan, K. Nakatani, Synthesis, crystal structures, and nonlinear optical (NLO) properties of new Schiff-base nickel (II) complexes. Toward a new type of molecular switch?, Inorg. Chem. 44(6) (2005) 1973-1982.

S. Di Bella, I. Fragalà, Synthesis and second-order nonlinear optical properties of bis (salicylaldiminato) M (II) metalloorganic materials, Synth. Met. 115(1) (2000) 191-196.

D.J. Williams, Organic Polymeric and Non?Polymeric Materials with Large Optical Nonlinearities, Angewandte Chemie International Edition in English 23(9) (1984) 690-703.

P. Günter, Nonlinear optical effects and materials, Springer2012.

P.N. Prasad, D.J. Williams, Introduction to nonlinear optical effects in molecules and polymers, Wiley New York etc.1991.

D.S. Chemla, Nonlinear optical properties of organic molecules and crystals, Elsevier2012.

M. Drozd, M. Marchewka, The structure, vibrational spectra and nonlinear optical properties of neutral melamine and singly, doubly and triply protonated melaminium cations—theoretical studies, J. Mol. Struct:Theochem 716(1) (2005) 175-192.

M.R.S.A. Janjua, Nonlinear optical response of a series of small molecules: quantum modification of ?-spacer and acceptor, Journal of the Iranian Chemical Society (2017) 1-14.

M.R.S.A. Janjua, M. Amin, M. Ali, B. Bashir, M.U. Khan, M.A. Iqbal, W. Guan, L. Yan, Z.M. Su, A DFT Study on The Two?Dimensional Second?Order Nonlinear Optical (NLO) Response of Terpyridine?Substituted Hexamolybdates: Physical Insight on 2D Inorganic–Organic Hybrid Functional Materials, Eur. J. Inorg. Chem. 2012(4) (2012) 705-711.

M.R.S.A. Janjua, M.U. Khan, B. Bashir, M.A. Iqbal, Y. Song, S.A.R. Naqvi, Z.A. Khan, Effect of ?-conjugation spacer (C C) on the first hyperpolarizabilities of polymeric chain containing polyoxometalate cluster as a side-chain pendant: A DFT study, Comp. Theor. Chem. 994 (2012) 34-40.

K.D. Singer, J.E. Sohn, L. King, H. Gordon, H. Katz, C. Dirk, Second-order nonlinear-optical properties of donor-and acceptor-substituted aromatic compounds, JOSA B 6(7) (1989) 1339-1350.

J. Luo, M. Haller, H. Ma, S. Liu, T.-D. Kim, Y. Tian, B. Chen, S.-H. Jang, L.R. Dalton, A.K.-Y. Jen, Nanoscale architectural control and macromolecular engineering of nonlinear optical dendrimers and polymers for electro-optics, J. Phys. Chem. B 108(25) (2004) 8523-8530.

M.R.S.A. Janjua, Z.-M. Su, W. Guan, C.-G. Liu, L.-K. Yan, P. Song, G. Maheen, Tuning second-order non-linear (NLO) optical response of organoimido-substituted hexamolybdates through halogens: Quantum design of novel organic-inorganic hybrid NLO materials, Aust. J. Chem. 63(5) (2010) 836-844.

M.R.S.A. Janjua, W. Guan, L. Yan, Z.-M. Su, M. Ali, I.H. Bukhari, Prediction of robustly large molecular second-order nonlinear optical properties of terpyridine-substituted hexamolybdates: Structural modelling towards a rational entry to NLO materials, J. Mol. Graphics Modell. 28(8) (2010) 735-745.

S.P. Karna, Y. Zhang, M. Samoc, P. Prasad, B.A. Reinhardt, A.G. Dillard, Nonlinear optical properties of novel thiophene derivatives: Experimental and ab initio time?dependent coupled perturbed Hartree–Fock studies, J. Chem. Phys. 99(12) (1993) 9984-9993.

J. Autschbach, Charge?Transfer Excitations and Time?Dependent Density Functional Theory: Problems and Some Proposed Solutions, Chemphyschem 10(11) (2009) 1757-1760.

A. Dreuw, M. Head-Gordon, Single-reference ab initio methods for the calculation of excited states of large molecules, Chem. Rev. 105(11) (2005) 4009-4037.

J. Preat, C. Michaux, D. Jacquemin, E.A. Perpete, Enhanced efficiency of organic dye-sensitized solar cells: triphenylamine derivatives, J. Phys. Chem. C 113(38) (2009) 16821-16833.

S. Kim, J.K. Lee, S.O. Kang, J. Ko, J.-H. Yum, S. Fantacci, F. De Angelis, D. Di Censo, M.K. Nazeeruddin, M. Grätzel, Molecular engineering of organic sensitizers for solar cell applications, J. Am. Chem. Soc. 128(51) (2006) 16701-16707.

D. Jacquemin, V. Wathelet, E.A. Perpete, C. Adamo, Extensive TD-DFT benchmark: singlet-excited states of organic molecules, J. Chem. Theory Comput. 5(9) (2009) 2420-2435.

M. Pastore, E. Mosconi, F. De Angelis, M. Gra?tzel, A computational investigation of organic dyes for dye-sensitized solar cells: benchmark, strategies, and open issues, J. Phys. Chem. C 114(15) (2010) 7205-7212.

A. Saylam, Z. Seferoglu, N. Ertan, Synthesis of new hetarylazoindole dyes from some 2-aminothiazole derivatives, Russ. J. Org. Chem. 44(4) (2008) 587-594.

V. Barone, M. Cossi, Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model, J. Phys. Chem. A 102(11) (1998) 1995-2001.

A. Karakas, A. Elmali, H. Unver, Linear optical transmission measurements and computational study of linear polarizabilities, first hyperpolarizabilities of a dinuclear iron (III) complex, Spectrochim. Acta. A Mol. Biomol. Spectrosc. 68(3) (2007) 567-572.

A. Karakas, A. Elmali, H. Unver, Linear optical transmission measurements and computational study of linear polarizabilities, first hyperpolarizabilities of a dinuclear iron(III) complex, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 68(3) (2007) 567-572.

Y.-J. Pu, M. Soma, H. Nishide, S. Shirai, J. Kido, Electroluminescence of poly (phenylenevinylene) s containing triphenylamine moieties in the main chain, Jpn. J. Appl. Phys. 41(1R) (2002) 362.

Z. Li, Z. Wu, W. Fu, P. Liu, B. Jiao, D. Wang, G. Zhou, X. Hou, Versatile fluorinated derivatives of triphenylamine as hole-transporters and blue-violet emitters in organic light-emitting devices, J. Phys. Chem. C 116(38) (2012) 20504-20512.

S.G. Bratsch, A group electronegativity method with Pauling units, J. Chem. Educ 62(2) (1985) 101.

D. O'Hagan, Understanding organofluorine chemistry. An introduction to the C–F bond, Chem. Soc. Rev. 37(2) (2008) 308-319.

R. Bralsford, P. Harris, W. Price, The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proceedings of the Royal Society of London A: Mathematical, Physical and Engineering Sciences, The Royal Society, 1960, pp. 459-469.

L.-K. Yan, M.-S. Jin, J. Zhuang, C.-G. Liu, Z.-M. Su, C.-C. Sun, Theoretical study on the considerable second-order nonlinear optical properties of naphthylimido-substituted hexamolybdates, J. Phys. Chem. A 112(40) (2008) 9919-9923.

M.R.S.A. Janjua, C.-G. Liu, W. Guan, J. Zhuang, S. Muhammad, L.-K. Yan, Z.-M. Su, Prediction of remarkably large second-order nonlinear optical properties of organoimido-substituted hexamolybdates, J. Phys. Chem. A 113(15) (2009) 3576-3587.

W. Guan, G. Yang, L. Yan, Z. Su, Prediction of second-order optical nonlinearity of trisorganotin-substituted ?-Keggin polyoxotungstate, Inorg. Chem. 45(19) (2006) 7864-7868.

Y. Wu, W. Zhu, Organic sensitizers from D–?–A to D–A–?–A: effect of the internal electron-withdrawing units on molecular absorption, energy levels and photovoltaic performances, Chem. Soc. Rev. 42(5) (2013) 2039-2058.

K.S. Thanthiriwatte, K.N. De Silva, Non-linear optical properties of novel fluorenyl derivatives—ab initio quantum chemical calculations, J. Mol. Struct:Theochem 617(1) (2002) 169-175.

J.-L. Oudar, D. Chemla, Hyperpolarizabilities of the nitroanilines and their relations to the excited state dipole moment, J. Chem. Phys. 66(6) (1977) 2664-2668.

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Published

2019-04-22

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Vol. 62 No. 3 (2018): Regular Issue

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Regular Articles

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