Linear polarizabilities and second hyperpolarizabilities of streptocyanines: Results from broken-Symmetry DFT and new CCSD(T) benchmarks

Xu, Lihua; Kumar, Anshuman; Wong, Bryan M.

doi:10.1002/jcc.25519

Title: Linear polarizabilities and second hyperpolarizabilities of streptocyanines: Results from broken-Symmetry DFT and new CCSD(T) benchmarks

Journal Article · 02 October 2018 · Journal of Computational Chemistry

DOI: https://doi.org/10.1002/jcc.25519 · OSTI ID:1612454

Xu, Lihua ^[1]; Kumar, Anshuman ^[2];

^[2]

Univ. of California, Riverside, CA (United States); DOE/OSTI
Univ. of California, Riverside, CA (United States)

In this work, we present a detailed analysis of the linear polarizability (α) and second hyperpolarizability (γ) in a series of streptocyanines, as predicted with various range-separated functionals and CCSD(T)-based methods. Contrary to previous work on these systems, we find that the lowest-energy electronic states for the larger streptocyanine oligomers are not closed-shell singlets, and improved accuracy can be obtained with certain DFT methods by allowing the system to relax to a lower-energy broken-symmetry solution. Our extensive analyses are complemented by new large-scale CCSD(T) and explicitly correlated CCSD(T)-F12 calculations that comprise the most complete and accurate benchmarks of α and γ for the streptocyanine systems to date. Taken together, our CCSD(T) and broken-symmetry DFT calculations (1) show that the MP2 benchmarks used in previous studies still exhibit significant errors (~ 25% for α and ~100% for γ) and, therefore, the MP2 calculations should not be used as reliable benchmarks for polarizabilities or hyperpolarizabilities, and (2) emphasize the importance of testing for a lower-energy open-shell configuration when calculating nonlinear optical properties for these systems. © 2018 Wiley Periodicals, Inc.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Univ. of California, Riverside, CA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC)

Grant/Contract Number:: SC0016269

OSTI ID:: 1612454

Journal Information:: Journal of Computational Chemistry, Journal Name: Journal of Computational Chemistry Journal Issue: 28 Vol. 39; ISSN 0192-8651

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (64)

Materials for Optical Data Storage Emmelius, Michael; Pawlowski, Georg; Vollmann, Hansj�rg W. Angewandte Chemie International Edition in English, Vol. 28, Issue 11 https://doi.org/10.1002/anie.198914453	journal	November 1989
Multiwfn: A multifunctional wavefunction analyzer Lu, Tian; Chen, Feiwu Journal of Computational Chemistry, Vol. 33, Issue 5 https://doi.org/10.1002/jcc.22885	journal	December 2011
Assessment of range-separated exchange functionals and nonempirical functional tuning for calculating the static second hyperpolarizabilities of streptocyanines Wang, Chao; Yuan, Yizhong; Tian, Xiaohui Journal of Computational Chemistry, Vol. 38, Issue 9 https://doi.org/10.1002/jcc.24716	journal	January 2017
Molpro: a general-purpose quantum chemistry program package: Molpro Werner, Hans-Joachim; Knowles, Peter J.; Knizia, Gerald Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 2 https://doi.org/10.1002/wcms.82	journal	July 2011
Nonlinear Optical Polymeric Materials: From Chromophore Design to Commercial Applications Dalton, Larry Polymers for Photonics Applications I https://doi.org/10.1007/3-540-44608-7_1	book	January 2002
Achieving Chemical Accuracy with Coupled-Cluster Theory Lee, Timothy J.; Scuseria, Gustavo E. Quantum Mechanical Electronic Structure Calculations with Chemical Accuracy https://doi.org/10.1007/978-94-011-0193-6_2	book	January 1995
On the performance of density functional theory for symmetry-breaking problems Sherrill, C. David; Lee, Michael S.; Head-Gordon, Martin Chemical Physics Letters, Vol. 302, Issue 5-6 https://doi.org/10.1016/S0009-2614(99)00206-7	journal	March 1999
A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP) Yanai, Takeshi; Tew, David P.; Handy, Nicholas C. Chemical Physics Letters, Vol. 393, Issue 1-3, p. 51-57 https://doi.org/10.1016/j.cplett.2004.06.011	journal	July 2004
The Importance of Short- and Long-Range Exchange on Various Excited State Properties of DNA Monomers, Stacked Complexes, and Watson–Crick Pairs Raeber, Alexandra E.; Wong, Bryan M. Journal of Chemical Theory and Computation, Vol. 11, Issue 5 https://doi.org/10.1021/acs.jctc.5b00105	journal	April 2015
Polarizabilities of π-Conjugated Chains Revisited: Improved Results from Broken-Symmetry Range-Separated DFT and New CCSD(T) Benchmarks Oviedo, M. Belén; Ilawe, Niranjan V.; Wong, Bryan M. Journal of Chemical Theory and Computation, Vol. 12, Issue 8 https://doi.org/10.1021/acs.jctc.6b00360	journal	July 2016
Accurate Electron Affinities and Orbital Energies of Anions from a Nonempirically Tuned Range-Separated Density Functional Theory Approach Anderson, Lindsey N.; Oviedo, M. Belén; Wong, Bryan M. Journal of Chemical Theory and Computation, Vol. 13, Issue 4 https://doi.org/10.1021/acs.jctc.6b01249	journal	March 2017
Halogen Bonding Interactions: Revised Benchmarks and a New Assessment of Exchange vs Dispersion Anderson, Lindsey N.; Aquino, Fredy W.; Raeber, Alexandra E. Journal of Chemical Theory and Computation, Vol. 14, Issue 1 https://doi.org/10.1021/acs.jctc.7b01078	journal	December 2017
Symmetry-Breaking in Cationic Polymethine Dyes: Part 2. Shape of Electronic Absorption Bands Explained by the Thermal Fluctuations of the Solvent Reaction Field Masunov, Artëm E.; Anderson, Dane; Freidzon, Alexandra Ya. The Journal of Physical Chemistry A, Vol. 119, Issue 26 https://doi.org/10.1021/acs.jpca.5b03877	journal	June 2015
Modeling the Photoelectron Spectra of MoNbO ₂ ^– Accounting for Spin Contamination in Density Functional Theory Thompson, Lee M.; Hratchian, Hrant P. The Journal of Physical Chemistry A, Vol. 119, Issue 32 https://doi.org/10.1021/acs.jpca.5b04625	journal	August 2015
Distinguishing the Effects of Bond-Length Alternation versus Bond-Order Alternation on the Nonlinear Optical Properties of π-Conjugated Chromophores Gieseking, Rebecca L.; Risko, Chad; Brédas, Jean-Luc The Journal of Physical Chemistry Letters, Vol. 6, Issue 12 https://doi.org/10.1021/acs.jpclett.5b00812	journal	May 2015
Optical Nonlinearities In Chemistry: Introduction Burland, Donald Chemical Reviews, Vol. 94, Issue 1 https://doi.org/10.1021/cr00025a600	journal	January 1994
Challenges for Density Functional Theory Cohen, Aron J.; Mori-Sánchez, Paula; Yang, Weitao Chemical Reviews, Vol. 112, Issue 1 https://doi.org/10.1021/cr200107z	journal	December 2011
Optoelectronic and Excitonic Properties of Oligoacenes: Substantial Improvements from Range-Separated Time-Dependent Density Functional Theory Wong, Bryan M.; Hsieh, Timothy H. Journal of Chemical Theory and Computation, Vol. 6, Issue 12 https://doi.org/10.1021/ct100529s	journal	November 2010
Time-Dependent Density-Functional Description of the ¹ L _a State in Polycyclic Aromatic Hydrocarbons: Charge-Transfer Character in Disguise? Richard, Ryan M.; Herbert, John M. Journal of Chemical Theory and Computation, Vol. 7, Issue 5 https://doi.org/10.1021/ct100607w	journal	April 2011
Charge-Transfer-Like π→π* Excitations in Time-Dependent Density Functional Theory: A Conundrum and Its Solution Kuritz, Natalia; Stein, Tamar; Baer, Roi Journal of Chemical Theory and Computation, Vol. 7, Issue 8 https://doi.org/10.1021/ct2002804	journal	July 2011
Excitation Gaps of Finite-Sized Systems from Optimally Tuned Range-Separated Hybrid Functionals Kronik, Leeor; Stein, Tamar; Refaely-Abramson, Sivan Journal of Chemical Theory and Computation, Vol. 8, Issue 5 https://doi.org/10.1021/ct2009363	journal	April 2012
Nonempirically Tuned Range-Separated DFT Accurately Predicts Both Fundamental and Excitation Gaps in DNA and RNA Nucleobases Foster, Michael E.; Wong, Bryan M. Journal of Chemical Theory and Computation, Vol. 8, Issue 8 https://doi.org/10.1021/ct300420f	journal	July 2012
Assessment of CCSD(T)-F12 Approximations and Basis Sets for Harmonic Vibrational Frequencies Martin, Jan M. L.; Kesharwani, Manoj K. Journal of Chemical Theory and Computation, Vol. 10, Issue 5 https://doi.org/10.1021/ct500174q	journal	April 2014
Optimum Exchange for Calculation of Excitation Energies and Hyperpolarizabilities of Organic Electro-optic Chromophores Garrett, Kerry; Sosa Vazquez, XochitlA; Egri, Shawn B. Journal of Chemical Theory and Computation, Vol. 10, Issue 9 https://doi.org/10.1021/ct500528z	journal	August 2014
Ultralarge and Thermally Stable Electro-Optic Activities from Supramolecular Self-Assembled Molecular Glasses Kim, Tae-Dong; Kang, Jae-Wook; Luo, Jingdong Journal of the American Chemical Society, Vol. 129, Issue 3 https://doi.org/10.1021/ja067970s	journal	January 2007
Reliable Prediction of Charge Transfer Excitations in Molecular Complexes Using Time-Dependent Density Functional Theory Stein, Tamar; Kronik, Leeor; Baer, Roi Journal of the American Chemical Society, Vol. 131, Issue 8 https://doi.org/10.1021/ja8087482	journal	March 2009
Challenging Compounds for Calculating Hyperpolarizabilities: p -Quinodimethane Derivatives de Wergifosse, Marc; Wautelet, Frédéric; Champagne, Benoît The Journal of Physical Chemistry A, Vol. 117, Issue 22 https://doi.org/10.1021/jp403163z	journal	May 2013
Impact of Bulk Aggregation on the Electronic Structure of Streptocyanines: Implications for the Solid-State Nonlinear Optical Properties and All-Optical Switching Applications Gieseking, Rebecca L.; Mukhopadhyay, Sukrit; Shiring, Stephen B. The Journal of Physical Chemistry C, Vol. 118, Issue 41 https://doi.org/10.1021/jp507920j	journal	October 2014
Polyradical Character and Spin Frustration in Fullerene Molecules: An Ab Initio Non-Collinear Hartree–Fock Study Jiménez-Hoyos, Carlos A.; Rodríguez-Guzmán, R.; Scuseria, Gustavo E. The Journal of Physical Chemistry A, Vol. 118, Issue 42 https://doi.org/10.1021/jp508383z	journal	October 2014
Two-photon polymerization initiators for three-dimensional optical data storage and microfabrication Cumpston, Brian H.; Ananthavel, Sundaravel P.; Barlow, Stephen Nature, Vol. 398, Issue 6722, p. 51-54 https://doi.org/10.1038/17989	journal	March 1999
Nonlinear magic: multiphoton microscopy in the biosciences Zipfel, Warren R.; Williams, Rebecca M.; Webb, Watt W. Nature Biotechnology, Vol. 21, Issue 11, p. 1369-1377 https://doi.org/10.1038/nbt899	journal	November 2003
How single conjugated polymer molecules respond to electric fields Schindler, Florian; Lupton, John M.; Müller, Josef Nature Materials, Vol. 5, Issue 2 https://doi.org/10.1038/nmat1549	journal	January 2006
Two-photon absorption properties of fluorescent proteins Drobizhev, Mikhail; Makarov, Nikolay S.; Tillo, Shane E. Nature Methods, Vol. 8, Issue 5 https://doi.org/10.1038/nmeth.1596	journal	April 2011
Quintuple-ζ quality coupled-cluster correlation energies with triple-ζ basis sets Tew, David P.; Klopper, Wim; Neiss, Christian Phys. Chem. Chem. Phys., Vol. 9, Issue 16 https://doi.org/10.1039/B617230J	journal	January 2007
Improved accuracy with medium cost computational methods for the evaluation of bond length alternation of increasingly long oligoacetylenes Sancho-García, J. C.; Pérez-Jiménez, A. J. Physical Chemistry Chemical Physics, Vol. 9, Issue 44 https://doi.org/10.1039/b710330a	journal	January 2007
Absorption and fluorescence properties of oligothiophene biomarkers from long-range-corrected time-dependent density functional theory Wong, Bryan M.; Piacenza, Manuel; Sala, Fabio Della Physical Chemistry Chemical Physics, Vol. 11, Issue 22 https://doi.org/10.1039/b901743g	journal	January 2009
Cationic cyanine dyes: impact of symmetry-breaking on optical absorption and third-order polarizabilities Yesudas, Kada Physical Chemistry Chemical Physics, Vol. 15, Issue 44 https://doi.org/10.1039/c3cp51718g	journal	January 2013
Assessing long-range corrected functionals with physically-adjusted range-separated parameters for calculating the polarizability and the second hyperpolarizability of polydiacetylene and polybutatriene chains Nénon, Sébastien; Champagne, Benoît; Spassova, Milena I. Physical Chemistry Chemical Physics, Vol. 16, Issue 15 https://doi.org/10.1039/c4cp00105b	journal	January 2014
A long-range-corrected time-dependent density functional theory Tawada, Yoshihiro; Tsuneda, Takao; Yanagisawa, Susumu The Journal of Chemical Physics, Vol. 120, Issue 18 https://doi.org/10.1063/1.1688752	journal	May 2004
Density functional theory investigation of the polarizability and second hyperpolarizability of polydiacetylene and polybutatriene chains: Treatment of exact exchange and role of correlation Champagne, Benoît; Bulat, Felipe A.; Yang, Weitao The Journal of Chemical Physics, Vol. 125, Issue 19 https://doi.org/10.1063/1.2388262	journal	November 2006
A simple and efficient CCSD(T)-F12 approximation Adler, Thomas B.; Knizia, Gerald; Werner, Hans-Joachim The Journal of Chemical Physics, Vol. 127, Issue 22 https://doi.org/10.1063/1.2817618	journal	December 2007
Calculation of electric dipole (hyper)polarizabilities by long-range-correction scheme in density functional theory: A systematic assessment for polydiacetylene and polybutatriene oligomers Kirtman, Bernard; Bonness, Sean; Ramirez-Solis, Alejandro The Journal of Chemical Physics, Vol. 128, Issue 11 https://doi.org/10.1063/1.2885051	journal	March 2008
Explicitly correlated RMP2 for high-spin open-shell reference states Knizia, Gerald; Werner, Hans-Joachim The Journal of Chemical Physics, Vol. 128, Issue 15 https://doi.org/10.1063/1.2889388	journal	April 2008
Simultaneous benchmarking of ground- and excited-state properties with long-range-corrected density functional theory Rohrdanz, Mary A.; Herbert, John M. The Journal of Chemical Physics, Vol. 129, Issue 3 https://doi.org/10.1063/1.2954017	journal	July 2008
Coumarin dyes for dye-sensitized solar cells: A long-range-corrected density functional study Wong, Bryan M.; Cordaro, Joseph G. The Journal of Chemical Physics, Vol. 129, Issue 21 https://doi.org/10.1063/1.3025924	journal	December 2008
Simplified CCSD(T)-F12 methods: Theory and benchmarks Knizia, Gerald; Adler, Thomas B.; Werner, Hans-Joachim The Journal of Chemical Physics, Vol. 130, Issue 5 https://doi.org/10.1063/1.3054300	journal	February 2009
A long-range-corrected density functional that performs well for both ground-state properties and time-dependent density functional theory excitation energies, including charge-transfer excited states Rohrdanz, Mary A.; Martins, Katie M.; Herbert, John M. The Journal of Chemical Physics, Vol. 130, Issue 5 https://doi.org/10.1063/1.3073302	journal	February 2009
Prediction of charge-transfer excitations in coumarin-based dyes using a range-separated functional tuned from first principles Stein, Tamar; Kronik, Leeor; Baer, Roi The Journal of Chemical Physics, Vol. 131, Issue 24 https://doi.org/10.1063/1.3269029	journal	December 2009
On the relationship between bond-length alternation and many-electron self-interaction error Körzdörfer, Thomas; Parrish, Robert M.; Sears, John S. The Journal of Chemical Physics, Vol. 137, Issue 12 https://doi.org/10.1063/1.4752431	journal	September 2012
Improved semiconductor lattice parameters and band gaps from a middle-range screened hybrid exchange functional Lucero, M. J.; Henderson, T. M.; Scuseria, G. E. Journal of Physics: Condensed Matter, Vol. 24, Issue 14 https://doi.org/10.1088/0953-8984/24/14/145504	journal	March 2012
Interactions between Light Waves in a Nonlinear Dielectric Armstrong, J. A.; Bloembergen, N.; Ducuing, J. Physical Review, Vol. 127, Issue 6 https://doi.org/10.1103/PhysRev.127.1918	journal	September 1962
Light Waves at the Boundary of Nonlinear Media Bloembergen, N.; Pershan, P. S. Physical Review, Vol. 128, Issue 2 https://doi.org/10.1103/PhysRev.128.606	journal	October 1962
Long-range–short-range separation of the electron-electron interaction in density-functional theory Toulouse, Julien; Colonna, François; Savin, Andreas Physical Review A, Vol. 70, Issue 6 https://doi.org/10.1103/PhysRevA.70.062505	journal	December 2004
Generation of Optical Harmonics Franken, P. A.; Hill, A. E.; Peters, C. W. Physical Review Letters, Vol. 7, Issue 4 https://doi.org/10.1103/PhysRevLett.7.118	journal	August 1961
Three-Dimensional Optical Storage Memory Parthenopoulos, D. A.; Rentzepis, P. M. Science, Vol. 245, Issue 4920 https://doi.org/10.1126/science.245.4920.843	journal	August 1989
Hartree–Fock stability and symmetry breaking: oxygen doubly negative ion Paldus, Josef; Čížek, Jiří Canadian Journal of Chemistry, Vol. 63, Issue 7 https://doi.org/10.1139/v85-301	journal	July 1985
Interactions between Light Waves in a Nonlinear Dielectric Armstrong, J. A.; Bloembergen, N.; Ducuing, J. A Volume in Honor of the 70th Birthday of Nicolaas Bloembergen, Resonances https://doi.org/10.1142/9789814540223_0041	conference	July 2014
Optimizing two-photon absorption for volumetric optical data storage Makarov, N. S.; Rebane, A.; Drobizhev, M. Journal of the Optical Society of America B, Vol. 24, Issue 8 https://doi.org/10.1364/JOSAB.24.001874	journal	January 2007
65 nm feature sizes using visible wavelength 3-D multiphoton lithography Haske, Wojciech; Chen, Vincent W.; Hales, Joel M. Optics Express, Vol. 15, Issue 6 https://doi.org/10.1364/OE.15.003426	journal	January 2007
Absorption and Fluorescence Properties of Oligothiophene Biomarkers from Long-Range-Corrected Time-Dependent Density Functional Theory Wong, Bryan M.; Piacenza, Manuel; Della Sala, Fabio arXiv https://doi.org/10.48550/arxiv.0904.3918	text	January 2009
Improved Semiconductor Lattice Parameters and Band Gaps from a Middle-Range Screened Hybrid Functional Lucero, Melissa J.; Henderson, Thomas M.; Scuseria, Gustavo E. arXiv https://doi.org/10.48550/arxiv.1111.4515	text	January 2011
Non-Empirically Tuned Range-Separated DFT Accurately Predicts Both Fundamental and Excitation Gaps in DNA and RNA Nucleobases Foster, Michael E.; Wong, Bryan M. arXiv https://doi.org/10.48550/arxiv.1209.5735	text	January 2012
Accurate Electron Affinities and Orbital Energies of Anions from a Non-Empirically Tuned Range-Separated Density Functional Theory Approach Anderson, Lindsey N.; Oviedo, M. Belén; Wong, Bryan M. arXiv https://doi.org/10.48550/arxiv.1803.01218	text	January 2018
Long-range/short-range separation of the electron-electron interaction in density functional theory Toulouse, Julien; Colonna, Francois; Savin, Andreas arXiv https://doi.org/10.48550/arxiv.physics/0410062	text	January 2004

Similar Records

Application of the explicitly correlated coupled-cluster models CCSD(F12*) and CC3(F12*) to the hyperpolarizability of the Ne atom

Journal Article · 2015 · AIP Conference Proceedings · OSTI ID:22390933

Hanauer, Matthias; Köhn, Andreas

Highly Accurate CCSD(T) and DFT–SAPT Stabilization Energies of H-Bonded and Stacked Structures of the Uracil Dimer

Journal Article · 2008 · Chemphyschem, 9(11):1636-1644 · OSTI ID:959183

Pitonak, Michal; Riley, Kevin E; Neogrady, Pavel; +1 more

Approximate spin projected spin-unrestricted density functional theory method: Application to diradical character dependences of second hyperpolarizabilities

Journal Article · 2015 · AIP Conference Proceedings · OSTI ID:22390901

Nakano, Masayoshi; Minami, Takuya; Fukui, Hitoshi; +5 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
CCSD(T)
Chemistry
DFT
broken-symmetry
hyperpolarizability
polarizability

Title: Linear polarizabilities and second hyperpolarizabilities of streptocyanines: Results from broken-Symmetry DFT and new CCSD(T) benchmarks

Citation Formats

References (64)

Similar Records

Related Subjects