Tuning the spectroscopic properties of aryl carotenoids by slight changes in structure

Journal of Physical Chemistry B

Volumn 119, Issue 4, 2015, Pages 1457-1467

  Fuciman, Marcel ^a   Keşan, Gürkan ^a   LaFountain, Amy M ^b   Frank, Harry A ^b   Polívka, Tomáš ^a  

^a UNIVERSITY OF SOUTH BOHEMIA   (Czech Republic)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; BOND LENGTH; COMPUTATION THEORY; FUNCTIONAL GROUPS; GROUND STATE; PIGMENTS; TORSIONAL STRESS;

CONJUGATED CHAIN; CONJUGATED SYSTEMS; EFFECTIVE CONJUGATION LENGTH; EQUILIBRIUM GEOMETRIES; FEMTOSECOND TRANSIENT ABSORPTION SPECTROSCOPY; PARTIAL DETACHMENT; PLANARIZATION; SPECTROSCOPIC PROPERTY;

DENSITY FUNCTIONAL THEORY;

CAROTENOID;

CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; SPECTROPHOTOMETRY;

CAROTENOIDS; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY;

EID: 84921968964     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp512354r     Document Type: Article

References (63)

1. Polívka, T.; Frank, H. A. Molecular Factors Controlling Photosynthetic Light-Harvesting by Carotenoids. Acc. Chem. Res. 2010, 43, 1125-1134.
2. Croce, R.; van Amerongen, H. Natural strategies for photosynthetic light harvesting. Nat. Chem. Biol. 2014, 10, 492-501.
3. Scholes, G. D.; Fleming, G. R.; Olaya-Castro, A.; van Grondelle, R. Lessons from nature about solar light harvesting. Nat. Chem. 2011, 3, 764-774.
4. Jahns, P.; Holzwarth, A. R. The role of the xanthophyll cycle and of lutein in photoprotection of photosystem II. Biochim. Biophys. Acta 2012, 1817, 182-193.
5. Edge, R.; Truscott, T. G. Carotenoid radicals and the interaction of carotenoids with active oxygen species. In The Photochemisry of Carotenoids; Frank, H. A., Young, A. J., Britton, G., Cogdell, R. J., Eds. Kluwer Academic Publishers: Dordrecht, 2004; pp 223-234.
6. McGraw, K. J. Mechanics of carotenoid-based coloration. In Bird Coloration Volume 1: Mechanisms and Measurements; Hill, G. E., McGraw, K. J., Eds.; Harvard University Press: Cambridge, MA, 2006; pp 177-242.
7. Tavan, P.; Schulten, K. Electronic excitations in finite and infinite polyenes. Phys. Rev. B 1987, 36, 4337-4358.
8. Polívka, T.; Sundström, V. Ultrafast dynamics of carotenoid excited states. From solution to natural and artificial systems. Chem. Rev. 2004, 104, 2021-2071.
9. Polívka, T.; Sundström, V. Dark excited states of carotenoids: Consensus and controversy. Chem. Phys. Lett. 2009, 477, 1-11.
10. Maiuri, M.; Polli, D.; Brida, D.; Luer, L.; LaFountain, A. M.; Fuciman, M.; Cogdell, R. J.; Frank, H. A.; Cerullo, G. Solvent-dependent activation of intermediate excited states in the energy relaxation pathways of spheroidene. Phys. Chem. Chem. Phys. 2012, 14, 6312-6319.
11. Buckup, T.; Motzkus, M. Multidimensional Time-Resolved Spectroscopy of Vibrational Coherence in Biopolyenes. Annu. Rev. Phys. Chem. 2014, 65, 39-57.
12. Jailaubekov, A. E.; Vengris, M.; Song, S. H.; Kusumoto, T.; Hashimoto, H.; Larsen, D. S. Deconstructing the Excited-State Dynamics of β-Carotene in Solution. J. Phys. Chem. A 2011, 115, 3905-3916.
13. 1 states in β-carotene homologs and lycopene on conjugation length studied by femtosecond time-resolved absorption and Kerr-gate fluorescence spectroscopies. J. Chem. Phys. 2009, 130, 214506.
14. 1 state of carotenoids having 11 conjugated C=C bonds. Chem. Phys. Lett. 2002, 355, 465-470.
15. - state. Biopolymers 2004, 74, 2-18.
16. Frank, H. A.; Cua, A.; Chynwat, V.; Young, A.; Gosztola, D.; Wasielewski, M. R. Photophysics of the Carotenoids Associated with the Xanthophyll Cycle in Photosynthesis. Photosynth. Res. 1994, 41, 389-395.
17. Niedzwiedzki, D.; Koscielecki, J. F.; Cong, H.; Sullivan, J. O.; Gibson, G. N.; Birge, R. R.; Frank, H. A. Ultrafast dynamics and excited state spectra of open-chain carotenoids at room and low temperatures. J. Phys. Chem. B 2007, 111, 5984-5998.
18. Mendes-Pinto, M. M.; Sansiaume, E.; Hashimoto, H.; Pascal, A. A.; Gall, A.; Robert, B. Electronic Absorption and Ground State Structure of Carotenoid Molecules. J. Phys. Chem. B 2013, 117, 11015-11021.
19. Christensen, R. L.; Enriquez, M. M.; Wagner, N. L.; Peacock-Villada, A. Y.; Scriban, C.; Schrock, R. R.; Polívka, T.; Frank, H. A.; Birge, R. R. Energetics and dynamics of the low-lying electronic states of constrained polyenes: Implications for infinite polyenes. J. Phys. Chem. A 2013, 117, 1449-1465.
20. Fujii, R.; Inaba, T.; Watanabe, Y.; Koyama, Y.; Zhang, J. P. Two different pathways of internal conversion in carotenoids depending on the length of the conjugated chain. Chem. Phys. Lett. 2003, 369, 165-172.
21. Chábera, P.; Fuciman, M.; Hříbek, P.; Polívka, T. Effect of carotenoid structure on excited state dynamics of carbonyl carotenoids. Phys. Chem. Chem. Phys. 2009, 11, 8795-8803.
22. Niedzwiedzki, D. M.; Kajikawa, T.; Aoki, K.; Katsumura, S.; Frank, H. A. Excited States Energies and Dynamics of Peridinin Analogues and the Nature of the Intramolecular Charge Transfer State in Carbonyl-Containing Carotenoids. J. Phys. Chem. B 2013, 117, 6874-6887.
23. Kleinschmidt, M.; Marian, C. M.; Waletzke, M.; Grimme, S. Parallel multireference configuration interaction calculations on mini-β-carotenes and β-carotene. J. Chem. Phys. 2009, 130, 044708.
24. Kosumi, D.; Kusumoto, T.; Fujii, R.; Sugisaki, M.; Iinuma, Y.; Oka, N.; Takaesu, Y.; Taira, T.; Iha, M.; Frank, H. A.; Hashimoto, H. Ultrafast excited state dynamics of fucoxanthin: excitation energy dependent intramolecular charge transfer dynamics. Phys. Chem. Chem. Phys. 2001, 13, 10762-10770.
25. Zigmantas, D.; Hiller, R. G.; Sharples, F. P.; Frank, H. A.; Sundström, V.; Polívka, T. Effect of conjugated carbonyl group on photophysical properties of carotenoids. Phys. Chem. Chem. Phys. 2004, 6, 3009-3016.
26. Frigaard, N. U.; Bryant, D. A. Chlorosomes: Antenna Organelles in Photosynthetic Green Bacteria. In Complex Intracellular Structures in Prokaryotes, Shively, J. M., Ed.; Springer: New York, 2010; p 79-114.
27. Gould, S. L.; Kodis, G.; Liddell, P. A.; Palacios, R. E.; Brune, A.; Gust, D.; Moore, T. A.; Moore, A. L. Artificial photosynthetic reaction centers with carotenoid antennas. Tetrahedron 2006, 62, 2074-2096.
28. Kloz, M.; Pillai, S.; Kodis, G.; Gust, D.; Moore, T. A.; Moore, A. L.; van Grondelle, R.; Kennis, J. T. M. Carotenoid Photoprotection in Artificial Photosynthetic Antennas. J. Am. Chem. Soc. 2011, 133, 7007-7015.
29. Pšenčík, J.; Ma, Y.-Z.; Arellano, J. B.; Garcia-Gil, L. J.; Holzwarth, A. R.; Gillbro, T. Excitation energy transfer in chlorosomes of Chlorobium phaeobacteroides strain CL1401: The role of carotenoids. Photosynth. Res. 2002, 71, 5-18.
30. Marian, C. M.; Kock, C. M.; Hundsdorfer, C.; Martin, H.-D.; Stahl, W.; Ostroumov, E.; Muller, M. G.; Holzwarth, A. R. Spectroscopic properties of phenolic and quinoid carotenoids: A combined theoretical and experimental study. Photochem. Photobiol. Sci. 2009, 8, 270-278.
31. Fuciman, M.; Chábera, P.; Župčanová, A.; Hříbek, P.; Arellano, J. B.; Vácha, F.; Pšenčík, J.; Polívka, T. Excited state properties of aryl carotenoids. Phys. Chem. Chem. Phys. 2010, 12, 3112-3120.
32. Niedzwiedzki, D. M.; Sullivan, J. O.; Polívka, T.; Birge, R. R.; Frank, H. A. Femtosecond time-resolved transient absorption spectroscopy of xanthophylls. J. Phys. Chem. B 2006, 110, 22872-22885.
33. Yamaguchi, M. On Carotenoids of a Sponge Reniera japonica. Bull. Chem. Soc. Jpn. 1957, 30, 111-114.
34. Graham, J. E.; Bryant, D. A. The Biosynthetic Pathway for Synechoxanthin, an Aromatic Carotenoid Synthesized by the Euryhaline, Unicellular Cyanobacterium Synechococcus sp. Strain PCC 7002. J. Bacteriol. 2008, 190, 7966-7974.
35. Ilagan, R. P.; Christensen, R. L.; Chapp, T. W.; Gibson, G. N.; Pascher, T.; Polívka, T.; Frank, H. A. Femtosecond time-resolved absorption spectroscopy of astaxanthin in solution and in alpha-crustacyanin. J. Phys. Chem. A 2005, 109, 3120-3127.
36. Kohn, W.; Sham, L. J. Self-Consistent Equations Including Exchange and Correlation Effects. Phys. Rev. 1965, 140, A1133-A1138.
37. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 1993, 98, 5648-5652.
38. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior. Phys. Rev. A 1988, 38, 3098-3100.
39. Lee, C.; Yang, W.; G. Parr, R. Development of the Colle-Salvetti Corelation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B 1988, 37, 785.
40. Schaefer, A.; Huber, C.; Ahlrichs, R. Fully Optimized Contracted Gaussian-Basis Sets of Triple Zeta Valence Quality for Atoms Li to Kr. J. Chem. Phys. 1994, 100, 5829-5853.
41. Hirata, S.; Head-Gordon, M. Time-Dependent Density Functional Theory within the Tamm-Dancoff Approximation. Chem. Phys. Lett. 1999, 314, 291-299.
42. 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.
43. Hsu, C.; Hirata, S.; Head-Gordon, M. Excitation Energies from Time-Dependent Density Functional Theory for Linear Polyene Oligomers. Butadiene to Decapentaene. J. Phys. Chem. A 2001, 105, 451-458.
44. 2 States of Violaxanthin, Zeaxanthin, and Lutein. J. Phys. Chem. A 2006, 110, 4592-4599.
45. 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.; et al. Gaussian, 09W; Gaussian Inc.: Wallingford, CT, 2009.
46. Dennington, T. A.; Keith, J. M. M. GaussView, 5.0.8; Gaussian Inc.: Wallingford, CT, 2008.
47. 1 State in Carotenoids. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4914-4917.
48. 1 internal conversion rate of β-carotene. J. Phys. Chem. A 1998, 102, 5049-5058.
49. de Weerd, F. L.; van Stokkum, I. H. M.; van Grondelle, R. Subpicosecond dynamics in the excited state absorption of all-trans-β-carotene. Chem. Phys. Lett. 2002, 354, 38-43.
50. van Stokkum, I. H. M.; Larsen, D. S.; van Grondelle, R. Global and target analysis of time-resolved spectra. Biochim. Biophys. Acta 2004, 1657, 82-104.
51. + state of all-trans-β-carotene newly identified in the near-infrared region. Photochem. Photobiol. 2001, 73, 219-222.
52. 1 state dynamics of the carotenoid spheroidene. J. Phys. Chem. B 2001, 105, 1072-1080.
53. Enriquez, M. M.; LaFountain, A. M.; Budarz, J.; Fuciman, M.; Gibson, G. N.; Frank, H. A. Direct determination of the excited state energies of the xanthophylls diadinoxanthin and diatoxanthin from Phaeodactylum tricornutum. Chem. Phys. Lett. 2010, 493, 353-357.
54. Billsten, H. H.; Herek, J. L.; Garcia-Asua, G.; Hashoj, L.; Polívka, T.; Hunter, C. N.; Sundström, V. Dynamics of energy transfer from lycopene to bacteriochlorophyll in genetically-modified LH2 complexes of Rhodobacter sphaeroides. Biochemistry 2002, 41, 4127-4136.
55. 1 Energies and Dynamics of Carotenoids. Chem. Phys. 1996, 194, 237-244.
56. - energies of all-trans-neurosporene and spheroidene as determined by fluorescence spectroscopy. Chem. Phys. Lett. 1998, 288, 847-853.
57. Papagiannakis, E.; van Stokkum, I. H. M.; van Grondelle, R.; Niederman, R. A.; Zigmantas, D.; Sundström, V.; Polívka, T. Near-infrared transitent absorption study of the excited state dynamics of the carotenoid spirilloxanthin in solution and in the LH1 complex of Rhodospirillum rubrum. J. Phys. Chem. B 2003, 107, 11216-11223.
58. Lukeš, V.; Christensson, N.; Milota, F.; Kauffmann, H. F.; Hauer, J. Electronic ground state conformers of β-carotene and their role in ultrafast spectroscopy. Chem. Phys. Lett. 2011, 506, 122-127.
59. Requena, A.; Ceron-Carrasco, J. P.; Bastida, A.; Zuniga, J.; Miguel, B. Density functional theory study of the structure and vibrational spectra of β-carotene, capsanthin, and capsorubin. J. Phys. Chem. A 2008, 112, 48-15-4825.
60. Young, A. J.; Phillip, D. M.; Hashimoto, H. Ring-to-chain conformation may be a determining factor in the ability of xanthophylls to bind to the bulk light-harvesting complex of plants. J. Mol. Struct. 2002, 642, 137-145.
61. 2 states of apo- and diapocarotenes. J. Phys. Chem. A 1999, 103, 2399-2407.
62. Polívka, T.; Kerfeld, C. A.; Pascher, T.; Sundström, V. Spectroscopic properties of the carotenoid 3′-hydroxyechinenone in the orange carotenoid protein from the cyanobacterium Arthrospira maxima. Biochemistry 2005, 44, 3994-4003.
63. Polívka, T.; Balashov, S. P.; Chábera, P.; Imasheva, E. S.; Yartsev, A.; Sundström, V.; Lanyi, J. K. Femtosecond carotenoid to retinal energy transfer in xanthorhodopsin. Biophys. J. 2009, 96, 2268-2277.