Enhanced intersystem crossing rate in polymethine-like molecules: Sulfur-containing squaraines versus oxygen-containing analogues

Journal of Physical Chemistry A

Volumn 117, Issue 11, 2013, Pages 2333-2346

  Peceli, Davorin ^a   Hu, Honghua ^a   Fishman, Dmitry A ^a   Webster, Scott ^a   Przhonska, Olga V ^a,b   Kurdyukov, Vladimir V ^c   Slominsky, Yurii L ^c   Tolmachev, Alexey I ^c   Kachkovski, Alexey D ^c   Gerasov, Andrey O ^c   Masunov, Artëm E ^a,d   Hagan, David J ^a   Van Stryland, Eric W ^a  

^a UNIVERSITY OF CENTRAL FLORIDA   (United States)

^b INSTITUTE OF HYDROBIOLOGY   (Ukraine)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^d UNIVERSITY OF CENTRAL FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY CALCULATIONS; ELECTRONIC CONFIGURATION; INTERSYSTEM CROSSING RATES; LINEAR AND NONLINEAR OPTICAL PROPERTIES; NONLINEAR CHARACTERIZATION; SINGLET AND TRIPLET STATE; SINGLET OXYGEN GENERATION; SPECTROSCOPIC CHARACTERIZATION;

ATOMS; AZO DYES; DENSITY FUNCTIONAL THEORY; DYES; MOLECULES; NUCLEAR PHYSICS; OXYGEN; QUANTUM YIELD; TWO PHOTON PROCESSES;

SULFUR;

BROMIDE; CYCLOBUTANE DERIVATIVE; INDOLE DERIVATIVE; OXYGEN; PHENOL DERIVATIVE; SELENIUM; SINGLET OXYGEN; SQUARAINE; SULFUR; VPM CHLORIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; PHOTON; QUANTUM THEORY; SPECTROFLUOROMETRY;

BROMIDES; CYCLOBUTANES; ELECTRONS; INDOLES; MOLECULAR STRUCTURE; OXYGEN; PHENOLS; PHOTONS; QUANTUM THEORY; SELENIUM; SINGLET OXYGEN; SPECTROMETRY, FLUORESCENCE; SULFUR;

EID: 84875422655     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp400276g     Document Type: Article

References (64)

1. Tyutyulkov, N. Polymethine Dyes Structure and Properties; Ohridski University Press: Sofia, St. Kliment, 1991.
2. Fabian, J.; Nakazumi, H.; Matsuoka, M. Near-Infrared Absorbing Dyes Chem. Rev. 1992, 92, 1197-1226
3. Spitler, M. T.; Ehret, A.; Kietzmann, R.; Willig, F. Electron Transfer Threshold for Spectral Sensitization of Silver Halides by Monomeric Cyanine Dyes J. Phys. Chem. B 1997, 101, 2552-2557
4. Dempsey, G. T.; Bates, M.; Kowtoniuk, W. E.; Liu, D. R.; Tsien, R. Y.; Zhuang, X. Photoswitching Mechanism of Cyanine Dyes J. Am. Chem. Soc. 2009, 131, 18192-18193
5. Christie, R. M. Colour Chemistry; The Royal Society of Chemistry: Cambridge, U.K., 2001.
6. Mishra, A.; Behera, R. K.; Behera, P. K.; Mishra, B. K.; Behera, G. B. Cyanines during the 1990s: A Review Chem. Rev. 2000, 100, 1973-2012
7. Fabian, J.; Nakazumi, H.; Matsuoka, M. Near-Infrared Absorbing Dyes Chem. Rev. 1992, 92, 1197-1226
8. Negres, R. A.; Przhonska, O. V.; Hagan, D. J.; Van Stryland, E. W.; Bondar, M. V.; Slominsky, Y. L.; Kachkovski, A. D. The Nature of Excited-State Absorption in Polymethine and Squarylium Molecules IEEE J. Sel. Top. Quantum Electron. 2001, 7, 849-863
9. Lepkowicz, R. S.; Przhonska, O. V.; Hales, J. M.; Fu, J.; Hagan, D. J.; Van Stryland, E. W.; Bondar, M. V.; Slominsky, Y. L.; Kachkovski, A. D. Nature of the Electronic Transitions in Thiacarbocyanines with a Long Polymethine Chain Chem. Phys. 2004, 305, 259-270
10. Lim, J. H.; Przhonska, O. V.; Khodja, S.; Yang, S.; Ross, T. S.; Hagan, D. J.; Van Stryland, E. W.; Bondar, M. V.; Slominsky, Y. L. Polymethine and Squarylium Molecules with Large Excited-State Absorption Chem. Phys. 1999, 245, 79-97
11. Beverina, L.; Crippa, M.; Landenna, M.; Ruffo, R.; Salice, P.; Silvestri, F.; Versari, S.; Villa, A.; Ciaffoni, L.; Collini, E.; Ferrante, C.; Bradamante, S.; Mari, C. M.; Bozio, R.; Pagani, G. A. Assessment of Water-Soluble Π-Extended Squaraines as One-and Two-Photon Singlet Oxygen Photosensitizers: Design, Synthesis, and Characterization J. Am. Chem. Soc. 2008, 130, 1894-1902
12. Santos, P. F.; Reis, L. V.; Duarte, I.; Serrano, J. P.; Almeida, P.; Oliveira, A. S.; Ferreira, L. F. V. Synthesis and Photochemical Evaluation of Iodinated Squarylium Cyanine Dyes Helv. Chim. Acta 2005, 88, 1135-1143
13. Salice, P.; Arnbjerg, J.; Pedersen, B. W.; Toftegaard, R.; Beverina, L.; Pagani, G. A.; Ogilby, P. R. Photophysics of Squaraine Dyes: Role of Charge-Transfer in Singlet Oxygen Production and Removal J. Phys. Chem. A 2010, 114, 2518-2525
14. Ogava, K.; Kobuke, Y. Recent Advances in Two-Photon Photodynamic Therapy Anti-Cancer Agents Med. Chem. 2008, 8, 269-279
15. Webster, S.; Peceli, D.; Hu, H.; Padilha, L. A.; Przhonska, O. V.; Masunov, A. E.; Gerasov, A. O.; Kachkovski, A. D.; Slominsky, Y. L.; Tolmachev, A. I. Near-Unity Quantum Yields for Intersystem Crossing and Singlet Oxygen Generation in Polymethine-Like Molecules: Design and Experimental Realization J. Phys. Chem. Lett. 2010, 1, 2354-2360
16. Brown, S. Photodynamic Therapy: Two Photons Are Better Than One Nat Photonics 2008, 2, 394-395
17. Starkey, J. R.; Rebane, A. K.; Drobizhev, M. A.; Meng, F.; Gong, A.; Elliott, A.; McInnerney, K.; Spangler, C. W. New Two-Photon Activated Photodynamic Therapy Sensitizers Induce Xenograft Tumor Regressions after Near-Ir Laser Treatment through the Body of the Host Mouse Clin. Cancer Res. 2008, 14, 6564-6573
18. Frederiksen, P. K.; Jørgensen, M.; Ogilby, P. R. Two-Photon Photosensitized Production of Singlet Oxygen J. Am. Chem. Soc. 2001, 123, 1215-1221
19. Dou, K.; Xiaodong, S.; Xiaojun, W.; Parkhill, R.; Yin, G.; Knobbe, E. T. Optical Limiting and Nonlinear Absorption of Excited States in Metalloporphyrin-Doped Sol Gels IEEE J. Quantum Electron. 1999, 35, 1004-1014
20. Xia, T.; Hagan, D. J.; Dogariu, A.; Said, A. A.; Van Stryland, E. W. Optimization of Optical Limiting Devices Based on Excited-State Absorption Appl. Opt. 1997, 36, 4110-4122
21. Lepkowicz, R.; Kobyakov, A.; Hagan, D. J.; Van Stryland, E. W. Picosecond Optical Limiting in Reverse Saturable Absorbers: A Theoretical and Experimental Study J. Opt. Soc. Am. B 2002, 19, 94-101
22. 60Derivatives Appl. Phys. Lett. 1999, 74, 332-334
23. Lawetz, V.; Orlandi, G.; Siebrand, W. Theory of Intersystem Crossing in Aromatic Hydrocarbons J. Chem. Phys. 1972, 56, 4058-4072
24. Robinson, G. W.; Frosch, R. P. Electronic Excitation Transfer and Relaxation J. Chem. Phys. 1963, 38, 1187-1203
25. Lower, S. K.; El-Sayed, M. A. The Triplet State and Molecular Electronic Processes in Organic Molecules Chem. Rev. 1966, 66, 199-241
26. Solov'ev, K. N.; Borisevich, E. A. Intramolecular Heavy-Atom Effect in the Photophysics of Organic Molecules Phys.-Usp. 2005, 48, 231-253
27. Schmidt, K.; Brovelli, S.; Coropceanu, V.; Beljonne, D.; Cornil, J.; Bazzini, C.; Caronna, T.; Tubino, R.; Meinardi, F.; Shuai, Z.; Brédas, J.-L. Intersystem Crossing Processes in Nonplanar Aromatic Heterocyclic Molecules J. Phys. Chem. A 2007, 111, 10490-10499
28. Detty, M. R.; Merkel, P. B. Chalcogenapyrylium Dyes as Potential Photochemotherapeutic Agents. Solution Studies of Heavy Atom Effects on Triplet Yields, Quantum Efficiencies of Singlet Oxygen Generation, Rates of Reaction with Singlet Oxygen, and Emission Quantum Yields J. Am. Chem. Soc. 1990, 112, 3845-3855
29. El-Sayed, M. A. Spin-Orbit Coupling and the Radiationless Processes in Nitrogen Heterocyclics J. Chem. Phys. 1963, 38, 2834-2838
30. Englman, R.; Jortner, J. The Energy Gap Law for Radiationless Transitions in Large Molecules Mol. Phys. 1970, 18, 145-164
31. Swatton, S. N. R.; Welford, K. R.; Hollins, R. C.; Sambles, J. R. A Time Resolved Double Pump-Probe Experimental Technique to Characterize Excited-State Parameters of Organic Dyes Appl. Phys. Lett. 1997, 71, 10-12
32. Peceli, D.; Webster, S.; Fishman, D. A.; Cirloganu, C. M.; Hu, H.; Przhonska, O. V.; Kurdyukov, V. V.; Slominsky, Y. L.; Tolmachev, A. I.; Kachkovski, A. D. Optimization of the Double Pump-Probe Technique: Decoupling the Triplet Yield and Cross Section J. Phys. Chem. A 2012, 116, 4833-4841
33. Sheik-Bahae, M.; Said, A. A.; Wei, T. H.; Hagan, D. J.; Van Stryland, E. W. Sensitive Measurement of Optical Nonlinearities Using a Single Beam IEEE J. Quantum Electron. 1990, 26, 760-769
34. Magde, D.; Brannon, J. H.; Cremers, T. L.; Olmsted, J. Absolute Luminescence Yield of Cresyl Violet. A Standard for the Red J. Phys. Chem. 1979, 83, 696-699
35. Lakowicz, J. R. Principles of Fluorescence Microscopy; Kluwer Academic: New York, 1999.
36. Przhonska, O. V.; Webster, S.; Padilha, L. A.; Hu, H.; Kachkovski, A. D.; Hagan, D. J.; Van Stryland, E. W. Two-Photon Absorption in Near-Ir Conjugated Molecules: Design Strategy and Structure-Property Relations Springer Ser. Fluoresc. 2010, 8, 105-148
37. Wilkinson, F.; Helman, W. P.; Ross, A. B. Quantum Yields for the Photosensitized Formation of the Lowest Electronically Excited Singlet State of Molecular Oxygen in Solution J. Phys. Chem. Ref. Data 1993, 22, 113-262
38. McClure, D. S. Triplet-Singlet Transitions in Organic Molecules. Lifetime Measurements of the Triplet State J. Chem. Phys. 1949, 17, 905-913
39. Guo, S.; Wu, W.; Guo, H.; Zhao, J. Room-Temperature Long-Lived Triplet Excited States of Naphthalenediimides and Their Applications as Organic Triplet Photosensitizers for Photooxidation and Triplet-Triplet Annihilation Upconversions J. Org. Chem. 2012, 77, 3933-3943
40. Kodama, N.; Sasaki, N.; Yamaga, M.; Masui, Y. Long-Lasting Phosphorescence of Eu2+ in Melilite J. Lumin. 2001, 94-95, 19-22
41. Perry, J. W.; Mansour, K.; Lee, I.-Y. S.; Wu, X.-L.; Bedworth, P. V.; Chen, C.-T.; Ng, D.; Marder, S. R.; Miles, P.; Wada, T.; Tian, M.; Sasabe, H. Organic Optical Limiter with a Strong Nonlinear Absorptive Response Science 1996, 273, 1533-1536
42. van Amerongen, H.; van Grondelle, R. In Methods Enzymol.; Kenneth, S., Ed.; Academic Press: 1995; Vol. 246, pp 201-226.
43. Maciejewski, A.; Naskrecki, R.; Lorenc, M.; Ziolek, M.; Karolczak, J.; Kubicki, J.; Matysiak, M.; Szymanski, M. Transient Absorption Experimental Set-up with Femtosecond Time Resolution. Femto-and Picosecond Study of Dcm Molecule in Cyclohexane and Methanol Solution J. Mol. Struct. 2000, 555, 1-13
44. Lessing, H. E.; Von Jena, A. Separation of Rotational Diffusion and Level Kinetics in Transient Absorption Spectroscopy Chem. Phys. Lett. 1976, 42, 213-217
45. van Veenendaal, M.; Chang, J.; Fedro, A. J. Model of Ultrafast Intersystem Crossing in Photoexcited Transition-Metal Organic Compounds Phys. Rev. Lett. 2010, 104, 067401-1-067401-2
46. Hedley, G. J.; Ruseckas, A.; Samuel, I. D. W. Ultrafast Intersystem Crossing in a Red Phosphorescent Iridium Complex J. Phys. Chem. A 2008, 113, 2-4
47. Ramakrishna, G.; Goodson, T.; Rogers-Haley, J. E.; Cooper, T. M.; McLean, D. G.; Urbas, A. Ultrafast Intersystem Crossing: Excited State Dynamics of Platinum Acetylide Complexes J. Phys. Chem. C 2008, 113, 1060-1066
48. Padilha, L. A.; Webster, S.; Hu, H.; Przhonska, O. V.; Hagan, D. J.; Van Stryland, E. W.; Bondar, M. V.; Davydenko, I. G.; Slominsky, Y. L.; Kachkovski, A. D. Excited State Absorption and Decay Kinetics of near Ir Polymethine Dyes Chem. Phys. 2008, 352, 97-105
49. Padilha, L. A.; Webster, S.; Przhonska, O. V.; Hu, H.; Peceli, D.; Rosch, J. L.; Bondar, M. V.; Gerasov, A. O.; Kovtun, Y. P.; Shandura, M. P. Nonlinear Absorption in a Series of Donor-Π-Acceptor Cyanines with Different Conjugation Lengths J. Mater. Chem. 2009, 19, 7503-7513
50. Rauh, R. D.; Leermakers, P. A. Solvent Effects Upon the Phosphorescence Lifetimes and Photoreactivity of Butyrophenone J. Am. Chem. Soc. 1968, 90, 2246-2249
51. Xu, C.; Webb, W. W. Measurement of Two-Photon Excitation Cross Sections of Molecular Fluorophores with Data from 690 to 1050 Nm J. Opt. Soc. Am. B 1996, 13, 481-491
52. Hales, J. M.; Hagan, D. J.; Stryland, E. W. V.; Schafer, K. J.; Morales, A. R.; Belfield, K. D.; Pacher, P.; Kwon, O.; Zojer, E.; Bredas, J. L. Resonant Enhancement of Two-Photon Absorption in Substituted Fluorene Molecules J. Chem. Phys. 2004, 121, 3152-3160
53. 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; Gaussian, Inc.: Wallingford, CT, 2009.
54. Becke, A. D. Density-Functional Thermochemistry. Iii. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
55. Rassolov, V. A.; Pople, J. A.; Ratner, M. A.; Windus, T. L. 6-31g[Sup] Basis Set for Atoms K through Zn J. Chem. Phys. 1998, 109, 1223-1229
56. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions J. Phys. Chem. B 2009, 113, 6378-6396
57. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. Molecular Excitation Energies to High-Lying Bound States from Time-Dependent Density-Functional Response Theory: Characterization and Correction of the Time-Dependent Local Density Approximation Ionization Threshold J. Chem. Phys. 1998, 108, 4439-4449
58. Fabian, J. Tddft-Calculations of Vis/Nir Absorbing Compounds Dyes Pigm. 2010, 84, 36-53
59. Masunov, A. E. Theoretical Spectroscopy of Carbocyanine Dyes Made Accurate by Frozen Density Correction to Excitation Energies Obtained by Td-Dft Int. J. Quantum Chem. 2010, 110, 3095-3100
60. Masunov, A.; Dannenberg, J. J. Theoretical Study of Urea. I. Monomers and Dimers J. Phys. Chem. A 1999, 103, 178-184
61. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. General Atomic and Molecular Electronic Structure System J. Comput. Chem. 1993, 14, 1347-1363
62. Fedorov, D. G.; Koseki, S.; Schmidt, M. W.; Gordon, M. S. Spin-Orbit Coupling in Molecules: Chemistry beyond the Adiabatic Approximation Int. Rev. Phys. Chem. 2003, 22, 551-592
63. Marian, C. M. Spin-Orbit Coupling and Intersystem Crossing in Molecules Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 187-203
64. Perun, S.; Tatchen, J.; Marian, C. M. Singlet and Triplet Excited States and Intersystem Crossing in Free-Base Porphyrin: Tddft and Dft/Mrci Study ChemPhysChem 2008, 9, 282-292