Implementation of INDO/SCI with COSMO Implicit Solvation and Benchmarking for Solvatochromic Shifts

Gieseking, Rebecca L.; Ratner, Mark A.; Schatz, George C.

doi:10.1021/acs.jpca.6b10487

Title: Implementation of INDO/SCI with COSMO Implicit Solvation and Benchmarking for Solvatochromic Shifts

Journal Article · Tue Dec 06 00:00:00 EST 2016 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.6b10487· OSTI ID:1594590

^[1]; Ratner, Mark A. ^[1];

^[1]

Northwestern Univ., Evanston, IL (United States)

Accurate and rapid quantum mechanical prediction of solvatochromic shifts, particularly in systems where charge transfer plays a significant role, is important for many aspects of molecular and material design. Although the semiempirical INDO/SCI approach is computationally efficient and performs well for charge-transfer states, the availability of implicit solvent approaches has been limited. As such, we implement the COSMO solvent model with a perturbative state-specific correction to the excited-state energies with the INDO/SCI method. We show that for a series of prototypical π-conjugated molecules, our newly implemented INDO/SCI/COSMO model yields more accurate absorption energies and comparably accurate solvatochromic shifts to those computed using TD-ωB97XD and CIS with COSMO solvation at a substantially lower computational cost.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Northwestern Univ., Evanston, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division

Grant/Contract Number:: SC0004752; FG02- 10ER16153

OSTI ID:: 1594590

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Vol. 120, Issue 49; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 5 works

Citation information provided by
Web of Science

References (67)

Electric Moments of Molecules in Liquids Onsager, Lars Journal of the American Chemical Society, Vol. 58, Issue 8 https://doi.org/10.1021/ja01299a050	journal	August 1936
The Dielectric Polarization of Polar Liquids Kirkwood, John G. The Journal of Chemical Physics, Vol. 7, Issue 10 https://doi.org/10.1063/1.1750343	journal	October 1939
COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2, Issue 5 https://doi.org/10.1039/P29930000799	journal	January 1993
Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model Cossi, Maurizio; Rega, Nadia; Scalmani, Giovanni Journal of Computational Chemistry, Vol. 24, Issue 6 https://doi.org/10.1002/jcc.10189	journal	April 2003
Self-Consistent Reaction Field Model for Aqueous and Nonaqueous Solutions Based on Accurate Polarized Partial Charges Marenich, Aleksandr V.; Olson, Ryan M.; Kelly, Casey P. Journal of Chemical Theory and Computation, Vol. 3, Issue 6 https://doi.org/10.1021/ct7001418	journal	October 2007
Calculation of UV/Vis Spectra in Solution Klamt, Andreas The Journal of Physical Chemistry, Vol. 100, Issue 9 https://doi.org/10.1021/jp950607f	journal	January 1996
Formation and relaxation of excited states in solution: A new time dependent polarizable continuum model based on time dependent density functional theory Caricato, Marco; Mennucci, Benedetta; Tomasi, Jacopo The Journal of Chemical Physics, Vol. 124, Issue 12 https://doi.org/10.1063/1.2183309	journal	March 2006
Full cLR-PCM calculations of the solvatochromic effects on emission energies Chibani, Siwar; Budzák, Šimon; Medved', Miroslav Phys. Chem. Chem. Phys., Vol. 16, Issue 47 https://doi.org/10.1039/C4CP03919J	journal	January 2014
Experimental Benchmark Data and Systematic Evaluation of Two a Posteriori , Polarizable-Continuum Corrections for Vertical Excitation Energies in Solution Mewes, Jan-Michael; You, Zhi-Qiang; Wormit, Michael The Journal of Physical Chemistry A, Vol. 119, Issue 21 https://doi.org/10.1021/jp511163y	journal	December 2014
Symmetry-adapted cluster and symmetry-adapted cluster-configuration interaction method in the polarizable continuum model: Theory of the solvent effect on the electronic excitation of molecules in solution Cammi, Roberto; Fukuda, Ryoichi; Ehara, Masahiro The Journal of Chemical Physics, Vol. 133, Issue 2 https://doi.org/10.1063/1.3456540	journal	July 2010
Coupled-cluster theories for the polarizable continuum model. II. Analytical gradients for excited states of molecular solutes by the equation of motion coupled-cluster method Cammi, R. International Journal of Quantum Chemistry, Vol. 110, Issue 15 https://doi.org/10.1002/qua.22884	journal	August 2010
A comparison between state-specific and linear-response formalisms for the calculation of vertical electronic transition energy in solution with the CCSD-PCM method Caricato, Marco The Journal of Chemical Physics, Vol. 139, Issue 4 https://doi.org/10.1063/1.4816482	journal	July 2013
A corrected-linear response formalism for the calculation of electronic excitation energies of solvated molecules with the CCSD-PCM method Caricato, Marco Computational and Theoretical Chemistry, Vol. 1040-1041 https://doi.org/10.1016/j.comptc.2014.02.001	journal	July 2014
Linear response theory for the polarizable continuum model Cammi, Roberto; Mennucci, Benedetta The Journal of Chemical Physics, Vol. 110, Issue 20 https://doi.org/10.1063/1.478861	journal	May 1999
Separation between Fast and Slow Polarizations in Continuum Solvation Models Cossi, Maurizio; Barone, Vincenzo The Journal of Physical Chemistry A, Vol. 104, Issue 46 https://doi.org/10.1021/jp000997s	journal	November 2000
Time-dependent density functional theory for molecules in liquid solutions Cossi, Maurizio; Barone, Vincenzo The Journal of Chemical Physics, Vol. 115, Issue 10 https://doi.org/10.1063/1.1394921	journal	September 2001
Coupled-cluster theory for the polarizable continuum model. III. A response theory for molecules in solution Cammi, R. International Journal of Quantum Chemistry, Vol. 112, Issue 13 https://doi.org/10.1002/qua.23271	journal	January 2012
Long-range charge-transfer excited states in time-dependent density functional theory require non-local exchange Dreuw, Andreas; Weisman, Jennifer L.; Head-Gordon, Martin The Journal of Chemical Physics, Vol. 119, Issue 6 https://doi.org/10.1063/1.1590951	journal	August 2003
Relationship between long-range charge-transfer excitation energy error and integer discontinuity in Kohn–Sham theory Tozer, David J. The Journal of Chemical Physics, Vol. 119, Issue 24 https://doi.org/10.1063/1.1633756	journal	December 2003
Failure of Time-Dependent Density Functional Theory for Long-Range Charge-Transfer Excited States: The Zincbacteriochlorin−Bacteriochlorin and Bacteriochlorophyll−Spheroidene Complexes Dreuw, Andreas; Head-Gordon, Martin Journal of the American Chemical Society, Vol. 126, Issue 12 https://doi.org/10.1021/ja039556n	journal	March 2004
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
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
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
Absorption and Fluorescence Spectra of Heterocyclic Isomers from Long-Range-Corrected Density Functional Theory in Polarizable Continuum Approach Kityk, Andriy V. The Journal of Physical Chemistry A, Vol. 116, Issue 11 https://doi.org/10.1021/jp300305j	journal	December 2011
Testing Computational Models of Hyperpolarizability in a Merocyanine Dye Using Spectroscopic and DFT Methods Reish, Matthew E.; Kay, Andrew J.; Teshome, Ayele The Journal of Physical Chemistry A, Vol. 116, Issue 22 https://doi.org/10.1021/jp301455r	journal	May 2012
The solvatochromism of phenolate betaines: comparing different cavities of a polarized continuum model Rezende, Marcos Caroli; Domínguez, Moisés Journal of Molecular Modeling, Vol. 21, Issue 8 https://doi.org/10.1007/s00894-015-2769-z	journal	July 2015
Theoretical analysis of charge-transfer electronic spectra of methylated benzenes—TCNE complexes including solvent effects: approaching experiment Mach, Pavel; Budzák, Šimon; Medveď, Miroslav Theoretical Chemistry Accounts, Vol. 131, Issue 9 https://doi.org/10.1007/s00214-012-1268-x	journal	September 2012
Critical analysis of spectral solvent shifts calculated by the contemporary PCM approaches of a representative series of charge-transfer complexes between tetracyanoethylene and methylated benzenes Budzák, Šimon; Mach, Pavel; Medved', Miroslav Physical Chemistry Chemical Physics, Vol. 17, Issue 27 https://doi.org/10.1039/C5CP01614B	journal	January 2015
Design of rigid donor-acceptor systems with a low-lying charge-transfer state: an INDO model study of barrelene-based compounds Fox, Thomas; Kotzian, Manfred; Roesch, Notker The Journal of Physical Chemistry, Vol. 97, Issue 44 https://doi.org/10.1021/j100146a014	journal	November 1993
DFT-INDO/S Modeling of New High Molar Extinction Coefficient Charge-Transfer Sensitizers for Solar Cell Applications Nazeeruddin, Mohammad K.; Wang, Qing; Cevey, Le Inorganic Chemistry, Vol. 45, Issue 2 https://doi.org/10.1021/ic051727x	journal	January 2006
Solvent Effects on the Electronic Spectra: An Extension of the Polarizable Continuum Model to the ZINDO Method Caricato, Marco; Mennucci, Benedetta; Tomasi, Jacopo The Journal of Physical Chemistry A, Vol. 108, Issue 29 https://doi.org/10.1021/jp048888r	journal	July 2004
Solvent polarity scales revisited: a ZINDO-PCM study of the solvatochromism of betaine-30 Caricato, Marco; Mennucci, Benedetta; Tomasi, Jacopo Molecular Physics, Vol. 104, Issue 5-7 https://doi.org/10.1080/00268970500417994	journal	March 2006
An intermediate neglect of differential overlap technique for spectroscopy: Pyrrole and the azines Ridley, J.; Zerner, Michael Theoretica Chimica Acta, Vol. 32, Issue 2 https://doi.org/10.1007/BF00528484	journal	January 1973
INDO/S parameters for gold Shapley, Warwick A.; Reimers, Jeffrey R.; Hush, Noel S. International Journal of Quantum Chemistry, Vol. 90, Issue 1 https://doi.org/10.1002/qua.10058	journal	January 2002
van der Waals Volumes and Radii Bondi, A. The Journal of Physical Chemistry, Vol. 68, Issue 3, p. 441-451 https://doi.org/10.1021/j100785a001	journal	March 1964
Synthesis, structure, and solvatochromism of merocyanine dyes based on barbituric acid Kulinich, A. V.; Derevyanko, N. A.; Ishchenko, A. A. Russian Journal of General Chemistry, Vol. 76, Issue 9 https://doi.org/10.1134/S1070363206090167	journal	September 2006
Electronic structure and fluorescent properties of malononitrile-based merocyanines with positive and negative solvatochromism Ishchenko, A. A.; Kulinich, A. V.; Bondarev, S. L. Optics and Spectroscopy, Vol. 104, Issue 1 https://doi.org/10.1134/S0030400X08010086	journal	January 2008
Merocyanines based on 1,3-indanedione: electronic structure and solvatochromism Kulinich, Andrii V.; Derevyanko, Nadia A.; Mikitenko, Elena K. Journal of Physical Organic Chemistry, Vol. 24, Issue 8 https://doi.org/10.1002/poc.1821	journal	December 2010
Systematic optimization of long-range corrected hybrid density functionals Chai, Jeng-Da; Head-Gordon, Martin The Journal of Chemical Physics, Vol. 128, Issue 8 https://doi.org/10.1063/1.2834918	journal	February 2008
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections Chai, Jeng-Da; Head-Gordon, Martin Physical Chemistry Chemical Physics, Vol. 10, Issue 44 https://doi.org/10.1039/b810189b	journal	January 2008
The influence of polarization functions on molecular orbital hydrogenation energies Hariharan, P. C.; Pople, J. A. Theoretica Chimica Acta, Vol. 28, Issue 3 https://doi.org/10.1007/BF00533485	journal	January 1973
Density-functional exchange-energy approximation with correct asymptotic behavior Becke, A. D. Physical Review A, Vol. 38, Issue 6 https://doi.org/10.1103/PhysRevA.38.3098	journal	September 1988
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Time-dependent density functional theory within the Tamm–Dancoff approximation Hirata, So; Head-Gordon, Martin Chemical Physics Letters, Vol. 314, Issue 3-4 https://doi.org/10.1016/S0009-2614(99)01149-5	journal	December 1999
Comparison of the Marcus and Pekar partitions in the context of non-equilibrium, polarizable-continuum solvation models You, Zhi-Qiang; Mewes, Jan-Michael; Dreuw, Andreas The Journal of Chemical Physics, Vol. 143, Issue 20 https://doi.org/10.1063/1.4936357	journal	November 2015
Advances in molecular quantum chemistry contained in the Q-Chem 4 program package Shao, Yihan; Gan, Zhengting; Epifanovsky, Evgeny Molecular Physics, Vol. 113, Issue 2 https://doi.org/10.1080/00268976.2014.952696	journal	September 2014
Application of the pople-santry-segal CNDO method to the cyclopropylcarbinyl and cyclobutyl cation and to bicyclobutane Wiberg, K. B. Tetrahedron, Vol. 24, Issue 3 https://doi.org/10.1016/0040-4020(68)88057-3	journal	January 1968
A Unified Description of Linear and Nonlinear Polarization in Organic Polymethine Dyes Marder, S. R.; Gorman, C. B.; Meyers, F. Science, Vol. 265, Issue 5172 https://doi.org/10.1126/science.265.5172.632	journal	July 1994
Electric Field Modulated Nonlinear Optical Properties of Donor-Acceptor Polyenes: Sum-Over-States Investigation of the Relationship between Molecular Polarizabilities (.alpha., .beta., and .gamma.) and Bond Length Alternation Meyers, F.; Marder, S. R.; Pierce, B. M. Journal of the American Chemical Society, Vol. 116, Issue 23 https://doi.org/10.1021/ja00102a040	journal	November 1994
Effect of Molecular Polarization on Bond-Length Alternation, Linear Polarizability, First and Second Hyperpolarizability in Donor-Acceptor Polyenes as a Function of Chain Length Gorman, Christopher B.; Marder, Seth R. Chemistry of Materials, Vol. 7, Issue 1 https://doi.org/10.1021/cm00049a033	journal	January 1995
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
25th Anniversary Article: Design of Polymethine Dyes for All-Optical Switching Applications: Guidance from Theoretical and Computational Studies Gieseking, Rebecca L.; Mukhopadhyay, Sukrit; Risko, Chad Advanced Materials, Vol. 26, Issue 1 https://doi.org/10.1002/adma.201302676	journal	October 2013
Understanding the Relationships Among Molecular Structure, Excited-State Properties, and Polarizabilities of π-Conjugated Chromophores Gieseking, Rebecca L.; Risko, Chad; Marder, Seth R. The WSPC Reference on Organic Electronics: Organic Semiconductors https://doi.org/10.1142/9789813148598_0011	book	June 2016
Toward a systematic molecular orbital theory for excited states Foresman, James B.; Head-Gordon, Martin; Pople, John A. The Journal of Physical Chemistry, Vol. 96, Issue 1 https://doi.org/10.1021/j100180a030	journal	January 1992
A comparison of single reference methods for characterizing stationary points of excited state potential energy surfaces Stanton, John F.; Gauss, Jürgen; Ishikawa, Naoto The Journal of Chemical Physics, Vol. 103, Issue 10 https://doi.org/10.1063/1.469601	journal	September 1995
Electronic Excitations of Simple Cyanine Dyes: Reconciling Density Functional and Wave Function Methods Send, Robert; Valsson, Omar; Filippi, Claudia Journal of Chemical Theory and Computation, Vol. 7, Issue 2 https://doi.org/10.1021/ct1006295	journal	December 2010
Longest-Wavelength Electronic Excitations of Linear Cyanines: The Role of Electron Delocalization and of Approximations in Time-Dependent Density Functional Theory Moore, Barry; Autschbach, Jochen Journal of Chemical Theory and Computation, Vol. 9, Issue 11 https://doi.org/10.1021/ct400649r	journal	September 2013
Taking Up the Cyanine Challenge with Quantum Tools Le Guennic, Boris; Jacquemin, Denis Accounts of Chemical Research, Vol. 48, Issue 3 https://doi.org/10.1021/ar500447q	journal	February 2015
0–0 Energies Using Hybrid Schemes: Benchmarks of TD-DFT, CIS(D), ADC(2), CC2, and BSE/ GW formalisms for 80 Real-Life Compounds Jacquemin, Denis; Duchemin, Ivan; Blase, Xavier Journal of Chemical Theory and Computation, Vol. 11, Issue 11 https://doi.org/10.1021/acs.jctc.5b00619	journal	October 2015
Benchmarking TD-DFT against Vibrationally Resolved Absorption Spectra at Room Temperature: 7-Aminocoumarins as Test Cases Muniz-Miranda, Francesco; Pedone, Alfonso; Battistelli, Giulia Journal of Chemical Theory and Computation, Vol. 11, Issue 11 https://doi.org/10.1021/acs.jctc.5b00750	journal	October 2015
Theoretical spectroscopy of BASHY dyes Laurent, Adèle D.; Le Guennic, Boris; Jacquemin, Denis Theoretical Chemistry Accounts, Vol. 135, Issue 7 https://doi.org/10.1007/s00214-016-1930-9	journal	July 2016
Computational Spectroscopy in Solution: Methods and Models for Investigating Complex Systems Barone, Vincenzo; Benassi, Enrico; Carnimeo, Ivan Challenges and Advances in Computational Chemistry and Physics https://doi.org/10.1007/978-3-319-21626-3_17	book	January 2015
Revisiting Vertical Models To Simulate the Line Shape of Electronic Spectra Adopting Cartesian and Internal Coordinates Cerezo, Javier; Santoro, Fabrizio Journal of Chemical Theory and Computation, Vol. 12, Issue 10 https://doi.org/10.1021/acs.jctc.6b00442	journal	September 2016
Electronic excitation of sulfur-organic compounds - performance of time-dependent density functional theory Fabian, Jürgen Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), Vol. 106, Issue 3 https://doi.org/10.1007/s002140100250	journal	July 2001
Insights into Current Limitations of Density Functional Theory Cohen, A. J.; Mori-Sanchez, P.; Yang, W. Science, Vol. 321, Issue 5890 https://doi.org/10.1126/science.1158722	journal	August 2008
Localization and Delocalization Errors in Density Functional Theory and Implications for Band-Gap Prediction Mori-Sánchez, Paula; Cohen, Aron J.; Yang, Weitao Physical Review Letters, Vol. 100, Issue 14 https://doi.org/10.1103/PhysRevLett.100.146401	journal	April 2008
Benchmarking Density Functional Theory Approaches for the Description of Symmetry Breaking in Long Polymethine Dyes Gieseking, Rebecca L.; Ravva, Mahesh Kumar; Coropceanu, Veaceslav The Journal of Physical Chemistry C, Vol. 120, Issue 18 https://doi.org/10.1021/acs.jpcc.6b02100	journal	May 2016

Similar Records

Integrated Quantum-Classical Protocol for the Realistic Description of Solvated Multinuclear Mixed-Valence Transition-Metal Complexes and Their Solvatochromic Properties

Journal Article · Tue Dec 12 00:00:00 EST 2023 · Journal of Chemical Theory and Computation · OSTI ID:1594590

Prampolini, Giacomo; Andersen, Amity; Poulter, Benjamin I.; +4 more

Benchmarking Semiempirical Methods To Compute Electrochemical Formal Potentials

Journal Article · Thu Jul 19 00:00:00 EDT 2018 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory · OSTI ID:1594590

Gieseking, Rebecca L. M.; Ratner, Mark A.; Schatz, George C.

Use of Solvatochromism to Assay Preferential Solvation of a Prototypic Catalytic Site

Journal Article · Wed Apr 01 00:00:00 EDT 2015 · Topics in Catalysis, 58(4-6):258-270 · OSTI ID:1594590

Schwenzer, Birgit; Cosimbescu, Lelia; Glezakou, Vassiliki Alexandra; +3 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Solvents
Energy
Absorption Molecules

Title: Implementation of INDO/SCI with COSMO Implicit Solvation and Benchmarking for Solvatochromic Shifts

Citation Formats

References (67)

Similar Records

Related Subjects