Can short- and middle-range hybrids describe the hyperpolarizabilities of long-range charge-transfer compounds?

Journal of Physical Chemistry A

Volumn 118, Issue 50, 2014, Pages 11787-11796

  Garza, Alejandro J ^a   Wazzan, Nuha A ^b   Asiri, Abdullah M ^b   Scuseria, Gustavo E ^a,b  

^a RICE UNIVERSITY   (United States)

^b KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR PHYSICS;

CHARGE-TRANSFER COMPOUNDS; EXCHANGE POTENTIALS; HARTREE-FOCK EXCHANGES; HYBRID FUNCTIONALS; HYPERPOLARIZABILITIES; KEY ELEMENTS; LONG-RANGE CORRECTIONS; SELF-INTERACTION ERROR;

CHARGE TRANSFER;

EID: 84918834053     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp510062b     Document Type: Article

References (92)

1. Dreuw, A.; Weisman, J. L.; Head-Gordon, M. Long-Range Charge-Transfer Excited States in Time-Dependent Density Functional Theory Require Non-Local Exchange. J. Chem. Phys. 2003, 119, 2943-2946.
2. Autschbach, J. Charge-Transfer Excitations and Time-Dependent Density Functional Theory: Problems and Some Proposed Solutions. ChemPhysChem 2009, 10, 1757-1760.
3. Oudar, J. L.; Chemla, D. S. Hyperpolarizabilities of the Nitroanilines and Their Relations to the Excited State Dipole Moment. J. Chem. Phys. 1977, 66, 2664-2668.
4. Reis, H. Problems in the Comparison of Theoretical and Experimental Hyperpolarizabilities Revisited. J. Chem. Phys. 2006, 125, 014506(1-9).
5. Champagne, B.; Kirtman, B. Evaluation of Alternative Sum-Over-States Expressions for the First Hyperpolarizability of Push-Pull π-Conjugated Systems. J. Chem. Phys. 2006, 125, 024101(1-7).
6. Garza, A. J.; Osman, O. I.; Wazzan, N. A.; Khan, S. B.; Asiri, A. M.; Scuseria, G. E. A Computational Study of the Nonlinear Optical Properties of Carbazole Derivatives: Theory Refines Experiment. Theor. Chem. Acc. 2014, 133, 1458(1-8).
7. Garza, A. J.; Osman, O. I.; Wazzan, N. A.; Khan, S. B.; Asiri, A. M.; Scuseria, G. E. Prediction of the Linear and Nonlinear Optical Properties of Tetrahydronaphthalone Derivatives Via Long-Range Corrected Hybrid Functionals. Mol. Phys. 2014, DOI: 10.1080/00268976.2014.934312.
8. Hurst, M.; Munn, R. W. In Organic Materials for Nonlinear Optics; Hann, R. A., Bloor, D., Eds.; The Royal Society of Chemistry: London, 1989.
9. Kanis, D. R.; Ratner, M. A.; Marks, T. J. Design and Construction of Molecular Assemblies with Large Second-Order Optical Nonlinearities. Quantum Chemical Aspect. Chem. Rev. 1994, 94, 195-242.
10. Ramakrishna, G.; Goodson, T., III. Excited-State Deactivation of Branched Two-Photon Absorbing Chromophores: A Femtosecond Transient Absorption Investigation. J. Phys. Chem. A 2007, 111, 993-1000.
11. Chakrabarti, S.; Ruud, K. Large Two-Photon Absorption Cross Section: Molecular Tweezer as a New Promising Class of Compounds for Nonlinear Optics. Phys. Chem. Chem. Phys. 2009, 11, 2592-2596.
12. Marder, S. R.; Sohn, J. E.; Stucky, G. D. Materials for Non-Linear Optics: Chemical Perspectives; ACS Symposium Series 45; American Chemical Society: Washington, DC, 1991.
13. Boyd, R. W. Nonlinear Optics; Academic Press: New York, 1992.
14. Marder, S. R. Organic Nonlinear Optical Materials: Where We Have Been and Where We Are Going. Chem. Commun. 2006, 2, 131-134.
15. Irie, M. Diarylethenes for Memories and Switches. Chem. Rev. 2000, 100, 1685-1716.
16. Kawata, S.; Kawata, Y. Three-Dimensional Optical Data Storage Using Photochromic Materials. Chem. Rev. 2000, 100, 1777-1788.
17. Tian, H.; Yang, S. Recent Progresses on Diarylethene Based Photochromic Switches. Chem. Soc. Rev. 2004, 33, 85-97.
18. Dvornikov, A. S.; Walker, E. P.; Rentzepis, P. M. Two-Photon Three-Dimensional Optical Storage Memory. J. Phys. Chem. A 2009, 113, 13633-13644.
19. Kurtz, H.; Dudis, D. Quantum Mechanical Methods for Predicting Nonlinear Optical Properties. Rev. Comput. Chem. 1998, 12, 241-279.
20. Sim, F.; Chin, S.; Dupuis, M.; Rice, J. E. Electron Correlation Effects in Hyperpolarizabilities of p-Nitroaniline. J. Phys. Chem. 1993, 97, 1158-1163.
21. Bulat, F. A.; Toro-Labbé, A.; Champagne, B.; Kirtman, B.; Yang, W. Density-Functional Theory (Hyper)polarizabilities of Push-Pull π-Conjugated Systems: Treatment of Exact Exchange and Role of Correlation. J. Chem. Phys. 2005, 123, 014319(1-7).
22. Bokhan, D.; Bartlett, R. J. Exact-Exchange Density Functional Theory for Hyperpolarizabilities. J. Chem. Phys. 2007, 127, 174102(1-9).
23. Champagne, B.; Perpète, E. A.; van Gisbergen, S. J. A.; Baerends, E. J.; Snijders, J. G.; Soubra-Ghaoui, C.; Robins, K. A.; Kirtman, B. Assessment of Conventional Density Functional Schemes for Computing the Polarizabilities and Hyperpolarizabilities of Conjugated Oligomers: An ab Initio Investigation of Polyacetylene Chains. J. Chem. Phys. 1998, 109, 10489-10498.
24. Champagne, B.; Perpète, E. A.; Jacquemin, D.; van Gisbergen, S. J. A.; Baerends, E. J.; Soubra-Ghaoui, C.; Robins, K. A.; Kirtman, B. Assessment of Conventional Density Functional Schemes for Computing the Dipole Moment and (Hyper)polarizabilities of Push-Pull π-Conjugated Systems. J. Phys. Chem. A 2000, 104, 4755-4763.
25. Loboda, O.; Zales̈ny, R.; Avramopoulos, A.; Luis, J. M.; Kirtman, B.; Tagmatarchis, N.; Reis, H.; Papadopoulos, M. G. Linear and Nonlinear Optical Properties of [60]Fullerene Derivatives. J. Phys. Chem. A 2009, 113, 1159-1170.
26. Garza, A. J.; Osman, O. I.; Scuseria, G. E.; Wazzan, N. A.; Khan, S. B.; Asiri, A. M. Nonlinear Optical Properties of DPO and DMPO: A Theoretical and Computational Study. Theor. Chem. Acc. 2013, 132, 1384(1-7).
27. Garza, A. J.; Osman, O. I.; Wazzan, N. A.; Khan, S. B.; Scuseria, G. E.; Asiri, A. M. Photochromic and Nonlinear Optical Properties of Fulgides: A Density Functional Theory Study. Comput. Theor. Chem. 2013, 1022, 82-85.
28. Chen, K. J.; Laurent, A. D.; Jacquemin, D. Strategies for Designing Diarylethenes as Efficient Nonlinear Optical Switches. J. Phys. Chem. C 2014, 118, 4334-4345.
29. Savin, A.; Flad, H. Density Functionals for the Yukawa Electron-Electron Interaction. Int. J. Quantum Chem. 1995, 56, 327-332.
30. Iikura, H.; Tsuneda, T.; Yanai, T.; Hirao, K. A Long-Range Correction Scheme for Generalized-Gradient-Approximation Exchange Functionals. J. Chem. Phys. 2001, 115, 3540-3544.
31. Yanai, T.; Tew, D. P.; Handy, N. C. A New Hybrid Exchange-Correlation Functional Using the Coulomb-Attenuating Method (CAM-B3LYP). Chem. Phys. Lett. 2004, 393, 51-57.
32. Vydrov, O. A.; Heyd, J.; Krukau, A. V.; Scuseria, G. E. Importance of Short-Range Versus Long-Range Hartree-Fock Exchange for the Performance of Hybrid Density Functionals. J. Chem. Phys. 2006, 125, 074106(1-9).
33. Vydrov, O. A.; Scuseria, G. E. Assessment of a Long-Range Corrected Hybrid Functional. J. Chem. Phys. 2006, 125, 234109(1-9).
34. Jacquemin, D.; Perpète, E. A.; Vydrov, O. A.; Scuseria, G. E.; Adamo, C. Assessment of Long-Range Corrected Functionals Performance for n → π ∗ Transitions in Organic Dyes. J. Chem. Phys. 2007, 127, 094102(1-6).
35. Tawada, Y.; Tsuneda, T.; Yanagisawa, S.; Yanai, T.; Hirao, K. A Long-Range-Corrected Time-Dependent Density Functional Theory. J. Chem. Phys. 2004, 120, 8425-8433.
36. Kamiya, M.; Sekino, H.; Tsuneda, T.; Hirao, K. Nonlinear Optical Property Calculations by the Long-Range-Corrected Coupled-Perturbed Kohn-Sham Method. J. Chem. Phys. 2005, 122, 234111(1- 10).
37. Jacquemin, D.; Perpète, E. A.; Scuseria, G. E.; Ciofini, I.; Adamo, C. TD-DFT Performance for the Visible Absorption Spectra of Organic Dyes: Conventional versus Long-Range Hybrids. J. Chem. Theory Comput. 2008, 4, 123-135.
38. Perpète, E. A.; Jacquemin, D.; Adamo, C.; Scuseria, G. E. Revisiting the Nonlinear Optical Properties of Polybutatriene and Polydiacetylene with Density Functional Theory. Chem. Phys. Lett. 2008, 456, 101-104.
39. Jacquemin, D.; Perpète, E. A.; Scuseria, G. E.; Ciofini, I.; Adamo, C. Extensive TD-DFT Investigation of the First Electronic Transition in Substituted Azobenzenes. Chem. Phys. Lett. 2008, 465, 226-229.
40. Song, J.; Watson, M. A.; Sekino, H.; Hirao, K. Nonlinear Optical Property Calculations of Polyynes with Long-Range Corrected Hybrid Exchange-Correlation Functionals. J. Chem. Phys. 2008, 129, 024117(1-8).
41. Zales̈ny, R.; Bulik, I. W.; Bartkowiak, W.; Luis, J. M.; Avramopoulos, A.; Papadopoulos, M. G.; Krawczyk, P. Electronic and Vibrational Contributions to First Hyperpolarizability of Donor-Acceptor-Substituted Azobenzene. J. Chem. Phys. 2010, 133, 244308(1-7).
42. de Wergifosse, M.; Champagne, B. Electron Correlation Effects on the First Hyperpolarizability of Push-pull π-Conjugated Systems. J. Chem. Phys. 2011, 134, 074113(1-13).
43. Jacquemin, D.; Perpète, E. A.; Medved, M.; Scalmani, G.; Frisch, M. J.; Kobayashi, R.; Adamo, C. First Hyperpolarizability of Polymethineimine with Long-Range Corrected Functionals. J. Chem. Phys. 2007, 126, 191108(1-4).
44. Nguyen, K. A.; Rogers, J. E.; Slagle, J. E.; Day, P. N.; Kannan, R.; Tan, L.; Fleitz, P. A.; Pachter, R. Effects of Conjugation in Length and Dimension on Spectroscopic Properties of Fluorene-Based Chromophores from Experiment and Theory. J. Phys. Chem. A 2006, 110, 13172-13182.
45. Zales̈ny, R.; Bulik, I. W.; Mikołajczyk, M.; Bartkowiak, W.; Luis, J. M.; Kirtman, B.; Avramopoulos, A.; Papadopoulos, M. G. Critical Assessment of Density Functional Theory for Computing Vibrational (Hyper)polarizabilities. AIP Conf. Proc. 2012, 1504, 655-658.
46. Garza, A. J.; Scuseria, G. E.; Khan, S. B.; Asiri, A. M. Assessment of Long-Range Corrected Functionals for the Prediction of Non-Linear Optical Properties of Organic Materials. Chem. Phys. Lett. 2013, 575, 122-125.
47. Bulik, I. W.; Zales̈ny, R.; Bartkowiak, W.; Luis, J. M.; Kirtman, B.; Scuseria, G. E.; Reis, H.; Avramopoulos, A.; Papadopoulos, M. G. Performance of Density Functional Theory in Computing Non-resonant Vibrational (Hyper)polarizabilities. J. Comput. Chem. 2013, 34, 1775-1784.
48. Lu, S.-I. Assessment of the Global and Range-Separated Hybrids for Computing the Dynamic Second-Order Hyperpolarizability of Solution-Phase Organic Molecules. Theor. Chem. Acc. 2014, 133, 1439.
49. Koopmans, T. Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den einzelnen Elektronen eines Atoms. Physica 1934, 1, 104-113.
50. Stein, T.; Kronik, L.; Baer, R. Reliable Prediction of Charge Transfer Excitations in Molecular Complexes Using Time-Dependent Density Functional Theory. J. Am. Chem. Soc. 2009, 131, 2818-2820.
51. Stein, T.; Kronik, L.; Baer, R. Prediction of Charge-Transfer Excitations in Coumarin-Based Dyes Using a Range-Separated Functional Tuned From First Principles. J. Chem. Phys. 2009, 131, 244119(1-5).
52. Stein, T.; Eisenberg, H.; Kronik, L.; Baer, R. Fundamental Gaps in Finite Systems from Eigenvalues of a Generalized Kohn-Sham Method. Phys. Rev. Lett. 2010, 105, 266802(1-4).
53. Karolewski, A.; Stein, T.; Kümmel, S. Tailoring the Optical Gap in Light-Harvesting Molecules. J. Chem. Phys. 2011, 134, 151101(1-4).
54. Sun, H.; Autschbach, J. Influence of the Delocalization Error and Applicability of Optimal Functional Tuning in Density Functional Calculations of Nonlinear Optical Properties of Organic Donor-Acceptor Chromophores. ChemPhysChem 2013, 14, 2450-2461.
55. Garza, A. J.; Osman, O. I.; Asiri, A. M.; Scuseria, G. E. Can Gap Tuning Schemes of Long-Range Corrected Hybrid Functionals Improve the Description of Hyperpolarizabilities? J. Phys. Chem. B 2014, DOI: 10.1021/jp507226v.
56. Garrett, K.; Sosa Vazquez, X. A.; Egri, S. B.; Wilmer, J.; Johnson, L. E.; Robinson, B. H.; Isborn, C. M. Optimum Exchange for Calculation of Excitation Energies and Hyperpolarizabilities of Organic Electro-optic Chromophores. J. Chem. Theory Comput. 2014, 10, 3821-3831.
57. Autschbach, J.; Srebro, M. Delocalization Error and "Functional Tuning" in Kohn-Sham Calculations of Molecular Properties. Acc. Chem. Res. 2014, 47, 2592-2602.
58. Asiri, A. M.; Faidallah, H. M.; Al-Nemari, K. F.; Ng, S. W.; Tienkink, E. R. T. (2E)-2-(Furan-2-ylmethylidene)-2,3-dihydro-1H-inden- 1-one. Acta Crystallogr. 2012, E68, o1065.
59. Asiri, A. M.; Faidallah, H. M.; Al-Nemari, K. F.; Ng, S. W.; Tienkink, E. R. T. (2E)-2-(40Bromobenzylidene)-2,3-dihydro-1H-inden- 1-one. Acta Crystallogr. 2012, E68, o755.
60. Asiri, A. M.; Faidallah, H. M.; Al-Nemari, K. F.; Ng, S. W.; Tienkink, E. R. T. (2E)-2-[(2H-1,3-Benzodioxol-5-yl)methylidene]-2,3-dihydro-1H-inden-1-one. Acta Crystallogr. 2012, E68, o1015.
61. Asiri, A. M.; Faidallah, H. M.; Al-Nemari, K. F.; Ng, S. W.; Tienkink, E. R. T. (2E)-2-(4-Methoxybenzylidene)-2,3-dihydro-1H-inden-1-one. Acta Crystallogr. 2012, E68, o915.
62. Henderson, T. M.; Izmaylov, A. F.; Scalmani, G.; Scuseria, G. E. Can Short-Range Hybrids Describe Long-Range-Dependent Properties? J. Chem. Phys. 2009, 131, 044108(1-9).
63. Tozer, D. J. Relationship between Long-Range Charge-Transfer Excitation Energy Error and Integer Discontinuity in Kohn-Sham Theory. J. Chem. Phys. 2003, 119, 12697-12699.
64. Heyd, J.; Scuseria, G. E.; Ernzerhof, M. Hybrid Functionals Based on a Screened Coulomb Potential. J. Chem. Phys. 2003, 118, 8207-8215.
65. Henderson, T. M.; Izmaylov, A. F.; Scuseria, G. E.; Savin, A. The Importance of Middle-Range Hartree-Fock-type Exchange for Hybrid Density Functionals. J. Chem. Phys. 2007, 127, 221103(1-4).
66. Henderson, T. M.; Izmaylov, A. F.; Scuseria, G. E.; Savin, A. Assessment of a Middle-Range Hybrid Functional. J. Chem. Theory Comput. 2008, 4, 1254-1262.
67. Perdew, J. P.; Parr, R. G.; Levy, M.; Balduz, J. L. Density-Functional Theory for Fractional Particle Number: Derivative Discontinuities of the Energy. Phys. Rev. Lett. 1982, 49, 1691-1694.
68. Willets, A.; Rice, J. E.; Burland, D. M.; Shelton, D. Problems in the Comparison of Theoretical and Experimental Hyperpolarizabilities. J. Chem. Phys. 1992, 97, 7590-7599.
69. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 09, Revision A.02; Gaussian Inc.: Wallingford, CT, 2009.
70. Suponitsky, K. Y.; Tafur, S.; Masunov, A. E. Applicability of Hybrid Density Functional Theory Methods to Calculation of Molecular Hyperpolarizability. J. Chem. Phys. 2008, 129, 044109(1-11).
71. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models. Chem. Rev. 2005, 105, 2999-3094.
72. Hammond, J. R.; Kowalski, K. Parallel Computation of Coupled-Cluster Hyperpolarizabilities. J. Chem. Phys. 2009, 130, 194108(1-11).
73. de Wergifosse, M.; Wautelet, F.; Champagne, B.; Kishi, R.; Fukuda, K.; Matsui, H.; Nakano, M. Challenging Compounds for Calculating Hyperpolarizabilities: p-Quinodimethane Derivatives. J. Phys. Chem. A 2013, 117, 4709-4715.
74. Vydrov, O. A.; Scuseria, G. E.; Perdew, J. P. Tests of Functionals for Systems with Fractional Electron Number. J. Chem. Phys. 2007, 126, 154109(1-9).
75. Drew, A.; Head-Gordon, M. Failure of Time-Dependent Density Functional Theory for Long-Range Charge-Transfer Excited States: The Zincbacteriochlorin-Bacteriochlorin and Bacteriochlorophyll-Spheroidene Complexes. J. Am. Chem. Soc. 2004, 126, 4007-4016.
76. Brown, P. Kinetic Studies in Mass Spectrometry - IX: Competing [M- NO2] and [M-NO] Reactions in Substituted Nitrobenzenes. Approximate Activation Energies from Ionization and Appearance Potentials. Org. Mass Spectrom. 1970, 4 (Suppl.), 533-544.
77. Chowdhurry, S.; Kishi, H.; Dillow, G. W.; Kebarle, P. Electron Affinities of Substituted Nitrobenzenes. Can. J. Chem. 1989, 67, 603-610.
78. Kosenov, D.; Slipchenko, L. V. Solvent Effects on the Electronic Transitions of p-Nitroaniline: A QM/EFP Study. J. Phys. Chem. A 2011, 115, 392-401.
79. Rösch, N.; Trickey, S. B. Comment on "Concerning the Applicability of Density Funtional Methods to Atomic and Molecular Negative Anions. J. Chem. Phys. 1997, 106, 8940-8941.
80. Sai, N.; Barbara, P. F.; Leung, K. Hole Localization in Molecular Crystals from Hybrid Density Functional Theory. Phys. Rev. Lett. 2011, 106, 226403(1-4).
81. Imamura, Y.; Kobayashi, R.; Nakai, H. Linearity Condition for Orbital Energies in Density Functional Theory (II): Application to Global Hybrid Functionals. Chem. Phys. Lett. 2011, 513, 130-135.
82. Atalla, V.; Yoon, M.; Caruso, F.; Rinke, P.; Scheffler, M. Hybrid Density Functional Theory Meets Quasiparticle Calculations: A Consistent Electronic Structure Approach. Phys. Rev. B 2013, 88, 165122(1-8).
83. Schmidt, T.; Kraisler, E.; Makmal, A.; Kronik, L.; Kümmel, S. A Self-Interaction-Free Local Hybrid Functional: Accurate Binding Energies vis-à-vis Accurate Ionization Potentials from Kohn-Sham Eigenvalues. J. Chem. Phys. 2014, 140, 18A510(1-14).
84. Staëhlin, M.; Moylan, C. R.; Burland, D. M.; Willets, A.; Rice, J. E.; Shelton, D. P.; Donley, E. A. A Comparison of Calculated and Experimental Hyperpolarizabilities for Acetonitrile in Gas and Liquid Phases. J. Chem. Phys. 1993, 98, 5595-5603.
85. Kaatz, P.; Donley, E. A.; Shelton, D. P. A Comparison of Molecular Hyperpolarizabilities From Gas and Liquid Phase Measurements. J. Chem. Phys. 1997, 108, 849-856.
86. Teng, C. C.; Garito, A. F. Dispersion of the Nonlinear Secondorder Optical Susceptibility of Organic Systems. Phys. Rev. B 1983, 28, 6766-6773.
87. Cheng, L.-T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.; Rikken, G.; Marder, S. R. Experimental Investigations of Organic Molecular Nonlinear Optical Polarizabilities. 1. Methods and Results on Benzene and Stilbene Derivatives. J. Phys. Chem. 1991, 95, 10631-10643.
88. Cheng, L.-T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.; Rikken, G.; Marder, S. R. Experimental Investigations of Organic Molecular Nonlinear Optical Polarizabilities. 2. A Study of Conjugation Dependences. J. Phys. Chem. 1991, 95, 10643-1052.
89. Day, P. N.; Pachter, R.; Nguyen, K. A. Analysis of Nonlinear Optical Properties in Donor-Acceptor Materials. J. Chem. Phys. 2014, 140, 184308(1-13).
90. Mikkelsen, K. V.; Luo, Y.; A˚gren, H.; Jørgensen, P. Solvent Induced Polarizabilities and Hyperpolarizabilities of para-Nitroaniline Studied by Reaction Field Linear Response Theory. J. Chem. Phys. 1994, 100, 8240-8250.
91. Jensen, L.; van Duijnen, P. T. The First Hyperpolarizability of p-Nitroaniline in 1,4-Dioxane: A Quantum Mechanical/Molecular Mechanics Study. J. Chem. Phys. 2005, 123, 074307(1-7).
92. Quinet, O.; Champagne, B.; Kirtman, B. Zero-Point Vibrational Averaging Correction for Second Harmonic Generation in para-Nitroaniline. J. Mol. Struct.: THEOCHEM 2003, 633, 199-207.