Solvent effects on cyanine derivatives: A PCM investigation

Journal of Physical Chemistry A

Volumn 118, Issue 28, 2014, Pages 5343-5348

  Jacquemin, Denis ^a,b   Chibani, Siwar ^a   Le Guennic, Boris ^c   Mennucci, Benedetta ^d  

^a UNIVERSITÉ DE NANTES   (France)

^b INSTITUT UNIVERSITAIRE DE FRANCE   (France)

^c INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^d UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CONTINUUM MECHANICS; ELECTRONIC PROPERTIES; EXCITED STATES; SOLVENTS;

EXCITED-STATE GEOMETRIES; FLUORESCENCE ENERGY; LINEAR RESPONSE; POLARIZABLE CONTINUUM MODEL; SOLVENT EFFECTS; THEORETICAL CHEMISTRY; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TRANSITION ENERGY;

GEOMETRY;

EID: 84904537629     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp504591t     Document Type: Article

References (48)

1. Dierksen, M.; Grimme, S. The Vibronic Structure of Electronic Absorption Spectra of Large Molecules: A Time-Dependent Density Functional Study on the Influence of "Exact" Hartree-Fock Exchange J. Phys. Chem. A 2004, 108, 10225-10237
2. Santoro, F.; Improta, R.; Lami, A.; Bloino, J.; Barone, V. Effective Method to Compute Franck-Condon Integrals for Optical Spectra of Large Molecules in Solution J. Chem. Phys. 2007, 126, 084509
3. 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
4. nD and CC2 Versions for the Treatment of Low-Lying Valence Excitations of Large Organic Dyes J. Chem. Phys. 2010, 132, 184103
5. Send, R.; Kühn, M.; Furche, F. Assessing Excited State Methods by Adiabatic Excitation Energies J. Chem. Theory Comput. 2011, 7, 2376-2386
6. Jacquemin, D.; Planchat, A.; Adamo, C.; Mennucci, B. A TD-DFT Assessment of Functionals for Optical 0-0 Transitions in Solvated Dyes J. Chem. Theory Comput. 2012, 8, 2359-2372
7. Winter, N. O. C.; Graf, N. K.; Leutwyler, S.; Hattig, C. Benchmarks for 0-0 Transitions of Aromatic Organic Molecules: DFT/B3LYP, ADC(2), CC2, SOS-CC2 and SCS-CC2 Compared to High-Resolution Gas-Phase Data Phys. Chem. Chem. Phys. 2013, 15, 6623-6630
8. Runge, E.; Gross, E. K. U. Density-Functional Theory for Time-Dependent Systems Phys. Rev. Lett. 1984, 52, 997-1000
9. Casida, M. E. Recent Advances in Density Functional Methods. In Time-Dependent Density-Functional Response Theory for Molecules; Chong, D. P., Ed.; World Scientific: Singapore, 1995; Vol. 1, pp 155-192.
10. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3094
11. Laurent, A. D.; Adamo, C.; Jacquemin, D. Dye Chemistry with Time-Dependent Density Functional Theory Phys. Chem. Chem. Phys. 2014, 16, 14334-14356
12. 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
13. Dreuw, 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 (Pubitemid 38391893)
14. Peach, M. J. G.; Benfield, P.; Helgaker, T.; Tozer, D. J. Excitation Energies in Density Functional Theory: An Evaluation and a Diagnostic Test J. Chem. Phys. 2008, 128, 044118
15. Laurent, A. D.; Jacquemin, D. TD-DFT Benchmarks: A Review Int. J. Quantum Chem. 2013, 113, 2019-2039
16. Schreiber, M.; Bub, V.; Fülscher, M. P. The Electronic Spectra of Symmetric Cyanine Dyes: A CASPT2 Study Phys. Chem. Chem. Phys. 2001, 3, 3906-3912 (Pubitemid 32916085)
17. Fabian, J. TDDFT-Calculations of Vis/NIR Absorbing Compounds Dyes Pigm. 2010, 84, 36-53
18. Send, R.; Valsson, O.; Filippi, C. Electronic Excitations of Simple Cyanine Dyes: Reconciling Density Functional and Wave Function Methods J. Chem. Theory Comput. 2011, 7, 444-455
19. Boulanger, P.; Jacquemin, D.; Duchemin, I.; Blase, X. Fast and Accurate Electronic Excitations in Cyanines with the Many-Body Bethe-Salpeter Approach J. Chem. Theory Comput. 2014, 10, 1212-1218
20. Grimme, S.; Neese, F. Double-Hybrid Density Functional Theory for Excited Electronic States of Molecules J. Chem. Phys. 2007, 127, 154116
21. Jacquemin, D.; Zhao, Y.; Valero, R.; Adamo, C.; Ciofini, I.; Truhlar, D. G. Verdict: Time-Dependent Density Functional Theory "Not Guilty" of Large Errors for Cyanines J. Chem. Theory Comput. 2012, 8, 1255-1259
22. Moore, B., II; Autschbach, J. Longest-Wavelength Electronic Excitations of Linear Cyanines: The Role of Electron Delocalization and of Approximations in Time-Dependent Density Functional Theory J. Chem. Theory Comput. 2013, 9, 4991-5003
23. Loudet, A.; Burgess, K. BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties Chem. Rev. 2007, 107, 4891-4932 (Pubitemid 350225866)
24. Ulrich, G.; Ziessel, R.; Harriman, A. The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed Angew. Chem., Int. Ed. 2008, 47, 1184-1201
25. Chibani, S.; Le Guennic, B.; Charaf-Eddin, A.; Maury, O.; Andraud, C.; Jacquemin, D. On the Computation of Adaiabtic Energies in Aza-Boron- Dipyrromethene Dyes J. Chem. Theory Comput. 2012, 8, 3303-3313
26. Chibani, S.; Le Guennic, B.; Charaf-Eddin, A.; Laurent, A. D.; Jacquemin, D. Revisiting the Optical Signatures of BODIPY with Ab Initio Tools Chem. Sci. 2013, 4, 1950-1963
27. 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
28. 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
29. Cammi, R.; Mennucci, B. The Linear Response Theory for the Polarizable Continuum Model J. Chem. Phys. 1999, 110, 9877-9886
30. Cossi, M.; Barone, V. Time-Dependent Density Functional Theory for Molecules in Liquid Solutions J. Chem. Phys. 2001, 115, 4708-4717 (Pubitemid 32902724)
31. Caricato, M.; Mennucci, B.; Tomasi, J.; Ingrosso, F.; Cammi, R.; Corni, S.; Scalmani, G. Formation and Relaxation of Excited States in Solution: A New Time Dependent Polarizable Continuum Model Based on Time Dependent Density Functional Theory J. Chem. Phys. 2006, 124, 124520
32. Improta, R.; Scalmani, G.; Frisch, M. J.; Barone, V. Toward Effective and Reliable Fluorescence Energies in Solution by a New State Specific Polarizable Continuum Model Time Dependent Density Functional Theory Approach J. Chem. Phys. 2007, 127, 074504
33. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G.; Guido, C. G.; Mennucci, B.; Scalmani, G.; Frisch, M. J. Practical Computation of Electronic Excitation in Solution: Vertical Excitation Model Chem. Sci. 2011, 2, 2143-2161
34. Charaf-Eddin, A.; Le Guennic, B.; Jacquemin, D. Optical Signatures of Borico Dyes: A TD-DFT Analysis Theor. Chem. Acc. 2014, 133, 1456
35. Chibani, S.; Laurent, A. D.; Blondel, A.; Mennucci, B.; Jacquemin, D. Excited-State Geometries of Solvated Molecules: Going Beyond the Linear-Response Polarizable Continuum Model J. Chem. Theory Comput. 2014, 10, 1848-1851
36. 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.; Gaussian 09, revision D.01; Gaussian Inc.: Wallingford, CT; 2009.
37. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals Theor. Chem. Acc. 2008, 120, 215-241
38. Li, R.; Zheng, J.; Truhlar, D. G. Density Functional Approximations for Charge Transfer Excitations with Intermediate Spatial Overlap Phys. Chem. Chem. Phys. 2010, 12, 12697-12701
39. Isegawa, M.; Peverati, R.; Truhlar, D. G. Performance of Recent and High-Performance Approximate Density Functionals for Time-Dependent Density Functional Theory Calculations of Valence and Rydberg Electronic Transition Energies J. Chem. Phys. 2012, 137, 244104
40. Leang, S. S.; Zahariev, F.; Gordon, M. S. Benchmarking the Performance of Time-Dependent Density Functional Methods J. Chem. Phys. 2012, 136, 104101
41. Jacquemin, D. New Cyanine Dyes or Not? Theoretical Insights for Model Chains J. Phys. Chem. A 2011, 115, 2442-2445
42. Valsson, O.; Filippi, C. Photoisomerization of Model Retinal Chromophores: Insight from Quantum Monte Carlo and Multiconfigurational Perturbation Theory J. Chem. Theory Comput. 2010, 6, 1275-1292
43. Guido, C. A.; Jacquemin, D.; Adamo, C.; Mennucci, B. On the TD-DFT Accuracy in Determining Single and Double Bonds in Excited-State Structures of Organic Molecules J. Phys. Chem. A 2010, 114, 13402-13410
44. 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
45. Bousquet, D.; Fukuda, R.; Maitarad, P.; Jacquemin, D.; Ciofini, I.; Adamo, C.; Ehara, M. Excited-State Geometries of Heteroaromatic Compounds: A Comparative TD-DFT and SAC-CI Study J. Chem. Theory Comput. 2013, 9, 2368-2379
46. Bousquet, D.; Fukuda, R.; Jacquemin, D.; Ciofini, I.; Adamo, C.; Ehara, M. Benchmark Study on the Triplet Excited-State Geometries and Phosphorescence Energies of Heterocyclic Compounds: Comparison Between TD-PBE0 and SAC-CI J. Chem. Theory Comput. 2014, 10.1021/ct5003797
47. Schmitt, A.; Hinkeldey, B.; Wild, M.; Jung, G. Synthesis of the Core Compound of the Bodipy Dye Class: 4,4′-Bora-(3a,4a)-diaza-s-Indacene J. Fluoresc. 2009, 19, 755-758
48. Xu, S.; Evans, R. E.; Liu, T.; Zhang, G.; Demas, J. N.; Trindle, C. O.; Fraser, C. L. Aromatic Difluoroboron β-Diketonate Complexes: Effects of π-Conjugation and Media on Optical Properties Inorg. Chem. 2013, 52, 3597-3610