Toward fully nonempirical simulations of optical band shapes of molecules in solution: A case study of heterocyclic ketoimine difluoroborates

Journal of Physical Chemistry A

Volumn 119, Issue 21, 2015, Pages 5145-5152

  Zales̈ny, Robert ^a   Murugan, N Arul ^a   Gel'Mukhanov, Faris ^a   Rinkevicius, Zilvinas ^a,b   Os̈miałowski, Borys ^c   Bartkowiak, Wojciech ^d   Ågren, Hans ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b Linköping University   (Sweden)

^c UNIVERSITY OF TECHNOLOGY AND LIFE SCIENCES   (Poland)

^d WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROMAGNETIC WAVE ABSORPTION; LIGHT ABSORPTION; MOLECULES; ORGANIC COMPOUNDS;

HYBRID APPROACH; HYBRID DENSITY FUNCTIONAL THEORY; INHOMOGENEOUS BROADENING; OPTICAL BANDS; TIME DEPENDENT; VIBRATIONAL FINE STRUCTURE; WAVE-PACKET APPROACH;

DENSITY FUNCTIONAL THEORY;

BORIC ACID; CHLOROFORM; HETEROCYCLIC COMPOUND; N,N DIMETHYLFORMAMIDE; SOLUTION AND SOLUBILITY; SOLVENT;

CHEMICAL MODEL; CHEMISTRY; MOLECULAR DYNAMICS; SOLUTION AND SOLUBILITY; SPECTROSCOPY; VIBRATION; WAVELET ANALYSIS;

BORATES; CHLOROFORM; DIMETHYLFORMAMIDE; HETEROCYCLIC COMPOUNDS; MODELS, CHEMICAL; MOLECULAR DYNAMICS SIMULATION; SOLUTIONS; SOLVENTS; SPECTRUM ANALYSIS; VIBRATION; WAVELET ANALYSIS;

EID: 84930654609     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp5094417     Document Type: Article

References (68)

1. Dreuw, A.; Head-Gordon, M. Single-Reference ab Initio Methods for the Calculation of Excited States of Large Molecules Chem. Rev. 2005, 105, 4009
2. Casida, M. E. Time-Dependent Density-Functional Theory for Molecules and Molecular Solids J. Mol. Struct. (THEOCHEM) 2009, 914, 3-18
3. Adamo, C.; Jacquemin, D. The Calculations of Excited-State Properties with Time-Dependent Density Functional Theory Chem. Soc. Rev. 2013, 42, 845-856
4. Charaf-Eddin, A.; Planchat, A.; Mennucci, B.; Adamo, C.; Jacquemin, D. Choosing a Functional for Computing Absorption and Fluorescence Band Shapes with TD-DFT J. Chem. Theory Comput. 2013, 9, 2749-2760
5. Laurent, A.; Jacquemin, D. TD-DFT Benchmarks: A Review Int. J. Quantum Chem. 2013, 113, 2019-2039
6. Jacquemin, D.; Perpéte, 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
7. Jacquemin, D.; Wathelet, V.; Perpéte, E. A.; Adamo, C. Extensive TD-DFT Benchmark: Singlet-Excited States of Organic Molecules J. Chem. Theory Comput. 2009, 5, 2420-2435
8. Jacquemin, D.; Moore, B.; Planchat, A.; Adamo, C.; Autschbach, J. Performance of an Optimally Tuned Range-Separated Hybrid Functional for 0-0 Electronic Excitation Energies J. Chem. Theory Comput. 2014, 10, 1677-1685
9. Okuno, K.; Shigeta, Y.; Kishi, R.; Miyasaka, H.; Nakano, M. Tuned CAM-B3LYP Functional in the Time-Dependent Density Functional Theory Scheme for Excitation Energies and Properties of Diarylethene Derivatives J. Photochem. Photobiol., A 2012, 235, 29-34
10. Vivas, M. G.; Silva, D. L.; Malinge, J.; Boujtita, M.; Zales̈ny, R.; Bartkowiak, W.; Ågren, H.; Canuto, S.; Boni, L. D.; Ishow, E. Molecular Structure-Optical Property Relationships for a Series of Non-Centrosymmetric Two-photon Absorbing Push-Pull Triarylamine Molecules Sci. Rep. 2014, 4, 4447
11. Bednarska, J.; Roztoczyńska, A.; Bartkowiak, W.; Zales̈ny, R. Comparative Assessment of Density Functionals for Excited-State Dipole Moments Chem. Phys. Lett. 2013, 584, 58-62
12. Lasorne, B.; Jornet-Somoza, J.; Meyer, H.-D.; Lauvergnat, D.; Robb, M. A.; Gatti, F. Vertical Transition Energies vs. Absorption Maxima: Illustration with the UV Absorption Spectrum of Ethylene Spectrochim. Acta, Part A 2014, 119, 52-58
13. Baiardi, A.; Bloino, J.; Barone, V. General Time Dependent Approach to Vibronic Spectroscopy Including Franck-Condon, Herzberg-Teller, and Duschinsky Effects J. Chem. Theory Comput. 2013, 9, 4097-4115
14. Silverstein, D. W.; Jensen, L. Vibronic Coupling Simulations for Linear and Nonlinear Optical Processes: Simulation Results J. Chem. Phys. 2012, 136, 064110
15. Weiss, P. A.; Silverstein, D. W.; Jensen, L. Non-Condon Effects on the Doubly Resonant Sum Frequency Generation of Rhodamine 6G J. Phys. Chem. Lett. 2014, 5, 329-335
16. Petrenko, T.; Neese, F. Efficient and Automatic Calculation of Optical Band Shapes and Resonance Raman Spectra for Larger Molecules Within the Independent Mode Displaced Harmonic Oscillator Model J. Chem. Phys. 2012, 137, 234107
17. Silverstein, D. W.; Govind, N.; van Dam, H. J. J.; Jensen, L. Simulating One-Photon Absorption and Resonance Raman Scattering Spectra Using Analytical Excited State Energy Gradients within Time-Dependent Density Functional Theory J. Chem. Theory Comput. 2013, 9, 5490-5503
18. Heller, E. J. The Semiclassical Way to Molecular Spectroscopy Acc. Chem. Res. 1981, 14, 368-375
19. Silverstein, D. W.; Jensen, L. Vibronic Coupling Simulations for Linear and Nonlinear Optical Processes: Theory J. Chem. Phys. 2012, 136, 064111
20. Chibani, S.; Charaf-Eddin, A.; Mennucci, B.; Le Guennic, B.; Jacquemin, D. Optical Signatures of OBO Fluorophores: A Theoretical Analysis J. Chem. Theory Comput. 2014, 10, 805-815
21. Charaf-Eddin, A.; Le Guennic, B.; Jacquemin, D. Optical Signatures of Borico Dyes: a TD-DFT analysis Theor. Chem. Acc. 2014, 133, 1456
22. Houari, Y.; Laurent, A. D.; Jacquemin, D. Spectral Signatures of Perylene Diimide Derivatives: Insights From Theory J. Phys. Chem. C 2013, 117, 21682-21691
23. Zakrzewska, A.; Zales̈ny, R.; Kolehmainen, E.; Os̈miałowski, B.; Jedrzejewska, B.; Ågren, H.; Pietrzak, M. Substituent Effects on the Photophysical Properties of Fluorescent 2-benzoylmethylenequinoline Difluoroboranes: A Combined Experimental and Quantum Chemical Study Dyes Pigm. 2013, 99, 957-965
24. Chibani, S.; Charaf-Eddin, A.; Le Guennic, B.; Jacquemin, D. Boranil and Related NBO Dyes: Insights From Theory J. Chem. Theory Comput. 2013, 9, 3127-3135
25. Le Guennic, B.; Chibani, S.; Charaf-Eddin, A.; Massue, J.; Ziessel, R.; Ulrich, G.; Jacquemin, D. The NBO Pattern in Luminescent Chromophores: Unravelling Excited-State Features Using TD-DFT Phys. Chem. Chem. Phys. 2013, 15, 7534-7540
26. Chibani, S.; Le Guennic, B.; Charaf-Eddin, A.; Maury, O.; Andraud, C.; Jacquemin, D. On the Computation of Adiabatic Energies in Aza-Boron-Dipyrromethene Dyes J. Chem. Theory Comput. 2012, 8, 3303-3313
27. Jacquemin, D.; Planchat, A.; Adamo, C.; Mennucci, B. TD-DFT Assessment of Functionals for Optical 0-0 Transitions in Solvated Dyes J. Chem. Theory Comput. 2012, 8, 2359-2372
28. Jacquemin, D.; Bremond, E.; Ciofini, I.; Adamo, C. Impact of Vibronic Couplings on Perceived Colors: Two Anthraquinones as a Working Example J. Phys. Chem. Lett. 2012, 3, 468-471
29. Jacquemin, D.; Bremond, E.; Planchat, A.; Ciofini, I.; Adamo, C. TD-DFT Vibronic Couplings in Anthraquinones: From Basis Set and Functional Benchmarks to Applications for Industrial Dyes J. Chem. Theory Comput. 2011, 7, 1882-1892
30. De Mitri, N.; Monti, S.; Prampolini, G.; Barone, V. Absorption and Emission Spectra of a Flexible Dye in Solution: A Computational Time-Dependent Approach J. Chem. Theory Comput. 2013, 9, 4507-4516
31. Mercer, I. P.; Gould, I. R.; Klug, D. R. Optical Properties of Solvated Molecules Calculated by a QMMM Method Chlorophyll a and Bacteriochlorophyll a Faraday Discuss. 1997, 108, 51-62
32. Walker, R. C.; de Souza, M. M.; Mercer, I. P.; Gould, I. R.; King, D. R. Large and Fast Relaxations Inside a Protein: Calculation and Measurement of Reorganization Energies in Alcohol Dehydrogenase J. Phys. Chem. B 2002, 106, 11658-11665
33. Mercer, I. P.; Gould, I. R.; King, D. R. A Quantum Mechanical/Molecular Mechanical Approach to Relaxation Dynamics: Calculation of the Optical Properties of Solvated Bacteriochlorophyll-a J. Phys. Chem. B 1999, 103, 7720-7727
34. Isborn, C. M.; Götz, A. W.; Clark, M. A.; Walker, R. C.; Martínez, T. J. Electronic Absorption Spectra from MM and ab Initio QM/MM Molecular Dynamics: Environmental Effects on the Absorption Spectrum of Photoactive Yellow Protein J. Phys. Chem. B 2012, 8, 5092-5106
35. Murugan, N. A.; Zales̈ny, R.; Kongsted, J.; Ågren, H. Chelation-Induced Quenching of Two-Photon Absorption of Azacrown Ether Substituted Distyryl Benzene for Metal Ion Sensing J. Chem. Theory Comput. 2014, 10, 778-788
36. Fonseca, T. L.; Coutinho, K.; Canuto, S. Polarization and Solvatochromic Shift of ortho -betaine in Water Chem. Phys. 2008, 349, 109-114
37. Silva, D. L.; Murugan, N. A.; Kongsted, J.; Rinkevicius, Z.; Canuto, S.; Ågren, H. The Role of Molecular Conformation and Polarizable Embedding for One- and Two-Photon Absorption of Disperse Orange 3 in Solution J. Phys. Chem. B 2012, 116, 8169-8181
38. Eilmes, A. Effect of Molecular Vibrations on the MD/QC-Simulated Absorption Spectra Int. J. Quantum Chem. 2014, 114, 261-270
39. Tomasi, J.; Persico, M. Molecular Interactions in Solution: An Overview of Methods Based on Continuous Distributions of the Solvent Chem. Rev. 1994, 94, 2027-2094
40. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3094
41. Ai, Y.; Tian, G.; Luo, Y. Role of Non-Condon Vibronic Coupling and Conformation Change on Two-Photon Absorption Spectra of Green Fluorescent Protein Mol. Phys. 2013, 111, 1316-1321
42. Ferrer, F. J. A.; Improta, R.; Santoro, F.; Barone, V. Computing the Inhomogeneous Broadening of Electronic Transitions in Solution: a First-Principle Quantum Mechanical Approach Phys. Chem. Chem. Phys. 2011, 13, 17007-17012
43. Ferrer, F. J. A.; Cerezo, J.; Soto, J.; Improta, R.; Santoro, F. First-Principle Computation of Absorption and Fluorescence Spectra in Solution Accounting for Vibronic Structure, Temperature Effects and Solvent Inhomogenous Broadening Comput. Theor. Chem. 2014, 1040-1041, 328-337
44. 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
45. Guido, C. A.; Knecht, S.; Kongsted, J.; Mennucci, B. Benchmarking Time-Dependent Density Functional Theory for Excited State Geometries of Organic Molecules in Gas-Phase and in Solution J. Chem. Theory Comput. 2013, 9, 2209-2220
46. Cammi, R.; Mennucci, B. Linear Response Theory for the Polarizable Continuum Model J. Chem. Phys. 1999, 110, 9877-9886
47. Cossi, M.; Barone, V. Time-Dependent Density Functional Theory for Molecules in Liquid Solutions J. Chem. Phys. 2001, 115, 4708-4717
48. Frisch, M. J.; GAUSSIAN 09, Revision D.01; Gaussian Inc.: Wallingford, CT, 2009.
49. Hättig, C.; Weigend, F. CC2 Excitation Energy Calculations on Large Molecules Using the Resolution of the Identity Approximation J. Chem. Phys. 2000, 113, 5154-5161
50. TURBOMOLE V6.4 2012, a Development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007; available from http://www.turbomole.com.
51. Amirjalayer, S.; Snurr, R. Q.; Schmid, R. Prediction of Structure and Properties of Boron-Based Covalent Organic Frameworks by a First-Principles Derived Force Field J. Phys. Chem. C 2012, 116, 4921-4929
52. Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. Development and Testing of a General AMBER Force Field J. Comput. Chem. 2004, 25, 1157-1174
53. Breneman, C. M.; Wiberg, K. B. Determining Atom-Centered Monopoles from Molecular Electrostatic Potentials. The Need for High Sampling Density in Formamide Conformational Analysis J. Comput. Chem. 1990, 11, 361-373
54. Case, D. A.; AMBER 11; University of California: San Francisco, 2010.
55. Nielsen, C. B.; Christiansen, O.; Mikkelsen, K. V.; Kongsted, J. Density Functional Self-Consistent Quantum Mechanics/Molecular Mechanics Theory for Linear and Nonlinear Molecular Properties: Applications to Solvated Water and Formaldehyde J. Chem. Phys. 2007, 126, 154112
56. Schwabe, T.; Sneskov, K.; Haugaard Olsen, J. M.; Kongsted, J.; Christiansen, O.; Hattig, C. PERI-CC2: A Polarizable Embedded RI-CC2Method J. Chem. Theory Comput. 2012, 8, 3274-3283
57. Gagliardi, L.; Lindh, R.; Karlström, G. Local Properties of Quantum Chemical Systems: The LoProp Approach J. Chem. Phys. 2004, 121, 4494-4500
58. Aidas, K. The Dalton Quantum Chemistry Program System Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2014, 4, 269-284
59. Petrenko, T.; Neese, F. Analysis and Prediction of Absorption Band Shapes, Fluorescence Band Shapes, Resonance Raman Intensities, and Excitation Profiles Using the Time-Dependent Theory of Electronic Spectroscopy J. Chem. Phys. 2007, 127, 164319
60. Neese, F. The ORCA program system Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 73-78
61. Frath, D.; Massue, J.; Ulrich, G.; Ziessel, R. Luminescent Materials: Locking π-Conjugated and Heterocyclic Ligands with Boron(III) Angew. Chem., Int. Ed. 2014, 53, 2290-2310
62. Gotor, R.; Costero, A. M.; Gil, S.; Gavina, P.; Rurack, K. On the Ion-Pair Recognition and Indication Features of a Fluorescent Heteroditopic Host Based on a BODIPY Core Eur. J. Org. Chem. 2014, 4005-4013
63. Singh, S. P.; Gayathri, T. Evolution of BODIPY Dyes as Potential Sensitizers for Dye-Sensitized Solar Cells Eur. J. Org. Chem. 2014, 4689-4707
64. Ni, Y.; Wu, J. Far-red and Near Infrared BODIPY Dyes: Synthesis and Applications for Fluorescent pH Probes and Bio-Imaging Org. Biomol. Chem. 2014, 12, 3774-3791
65. Pan, Z.-H.; Luo, G.-G.; Zhou, J.-W.; Xia, J.-X.; Fang, K.; Wu, R.-B. A Simple BODIPY-aniline-based Fluorescent Chemosensor as Multiple Logic Operations for the Detection of pH and CO2 Gas Dalton Trans. 2014, 43, 8499-8507
66. Yu, X.; Jia, X.; Yang, X.; Liu, W.; Qin, W. Synthesis and Photochemical Properties of BODIPY-Functionalized Silica Nanoparticle for Imaging Cu2+ in Living cells RSC Adv. 2014, 4, 23571-23579
67. Myers, A. B. Molecular Electronic Spectral Broadening In Liquids and Glasses Annu. Rev. Phys. Chem. 1998, 49, 267-95
68. Boulanger, P.; Chibani, S.; Guennic, B. L.; Duchemin, I.; Blase, X.; Jacquemin, D. Combining the Bethe-Salpeter Formalism with Time-Dependent DFT Excited-State Forces to Describe Optical Signatures: NBO Fluoroborates as Working Examples J. Chem. Theory Comput. 2014, 10, 4548-4556