Photophysical properties and electronic structure of stable, tunable synthetic bacteriochlorins: Extending the features of native photosynthetic pigments

Journal of Physical Chemistry B

Volumn 115, Issue 37, 2011, Pages 10801-10816

  Yang, Eunkyung ^a   Kirmaier, Christine ^a   Krayer, Michael ^b   Taniguchi, Masahiko ^b   Kim, Han Je ^b   Diers, James R ^c   Bocian, David F ^c   Lindsey, Jonathan S ^b   Holten, Dewey ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMOPHORES; DENSITY FUNCTIONAL THEORY; DYES; ELECTRONIC STRUCTURE; EXCITED STATES; FLOW CYTOMETRY; INFRARED DEVICES; MOLECULAR ORBITALS; NITROGEN COMPOUNDS; PHOTODYNAMIC THERAPY; PORPHYRINS; QUANTUM YIELD;

BACTERIOCHLORINS; BACTERIOCHLOROPHYLLS; CHLORINS; DENSITY FUNCTIONAL THEORY CALCULATIONS; DESIGN PRINCIPLES; DFT CALCULATION; EXCITED SINGLET STATE; FLUORESCENCE QUANTUM YIELD; FRONTIER MOLECULAR ORBITALS; LOWEST UNOCCUPIED MOLECULAR ORBITAL; MACROCYCLES; MOLECULAR IMAGING; NATURAL PIGMENT; NEAR-INFRARED ABSORBERS; NIR REGIONS; OXIDATIVE CONVERSION; PHOTOPHYSICAL; PHOTOPHYSICAL PROPERTIES; PHOTOSYNTHETIC PIGMENTS; PRE-SELECTED; REDUCED PYRROLE RINGS; SOLAR LIGHT; SPECTRAL PROPERTIES; SYNTHETIC MANIPULATIONS; SYNTHETIC METHODOLOGY; TETRAPYRROLES;

BACTERIOLOGY;

EID: 80052828697     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp205258s     Document Type: Article

References (74)

1. Scheer, H. Chlorophylls and Bacteriochlorophylls. Biochemistry, Biophysics, Functions and Applications. Advances in Photosynthesis and Respiration Grimm, B., Porra, R. J., Rüdiger, W., Scheer, H., Eds.; Springer: Dordrecht, The Netherlands, 2006; Vol. 25, pp 1-26.
2. Ashur, I.; Goldschmidt, R.; Pinkas, I.; Salomon, Y.; Szewczyk, G.; Sarna, T.; Scherz, A. J. Phys. Chem. A 2009, 113, 8027-8037
3. Kozyrev, A. N.; Chen, Y.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, R. K. J. Org. Chem. 2006, 71, 1949-1960
4. Limantara, L.; Koehler, P.; Wilhelm, B.; Porra, R. J.; Scheer, H. Photochem. Photobiol. 2006, 82, 770-780
5. Vakrat-Haglili, Y.; Weiner, L.; Brumfeld, V.; Brandis, A.; Salomon, Y.; McIlroy, B.; Wilson, B. C.; Pawlak, A.; Rozanowska, M.; Sarna, T.; Scherz, A. J. Am. Chem. Soc. 2005, 127, 6487-6497
6. Fiedor, J.; Fiedor, L.; Kammhuber, N.; Scherz, A.; Scheer, H. Photochem. Photobiol. 2002, 76, 145-152
7. Grin, M. A.; Mironov, A. F.; Shtil, A. A. Anti-Cancer Agents Med. Chem. 2008, 8, 683-697
8. Chen, Y.; Li, G.; Pandey, R. K. Curr. Org. Chem. 2004, 8, 1105-1134
9. Galezowski, M.; Gryko, D. T. Curr. Org. Chem. 2007, 11, 1310-1338
10. Aratani, N.; Osuka, A. In Handbook of Porphyrin Science; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; World Scientific Publishing Co.: Singapore, 2010; Vol. 1, pp 1-132.
11. Maretina, I. A. Russ. J. Gen. Chem. 2009, 79, 1544-1581
12. Flamigni, L. J. Photochem. Photobiol. C: Photochem. Rev. 2007, 8, 191-210
13. Iengo, E.; Scandola, F.; Alessio, E. Struct. Bonding (Berlin) 2006, 121, 105-143
14. Harvey, P. D. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, CA, 2003; Vol. 18, pp 63-250.
15. Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57-69
16. Gust, D.; Moore, T. A. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8, pp 153-190.
17. Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979
18. Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461
19. Wasielewski, M. R. In Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, USA, 1991; pp 269-286.
20. Lindsey, J. S.; Mass, O.; Chen, C.-Y. New J. Chem. 2011, 35, 511-516
21. Kobayashi, M.; Akiyama, M.; Kano, H.; Kise, H. In Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications; Grimm, B.; Porra, R. J.; Rüdiger, W.; Scheer, H., Eds.; Springer: Dordrecht, The Netherlands, 2006; pp 79-94.
22. Stromberg, J. R.; Marton, A.; Kee, H. L.; Kirmaier, C.; Diers, J. R.; Muthiah, C.; Taniguchi, M.; Lindsey, J. S.; Bocian, D. F.; Meyer, G. J.; Holten, D. J. Phys. Chem. C 2007, 111, 15464-15478
23. Chattopadhyay, P. K.; Hogerkorp, C.-M.; Roederer, M. Immunologoy 2008, 125, 441-449
24. Shapiro, H. M. In Flow Cytometry for Biotechnology; Sklar, L. A., Ed.; Oxford University Press: NY,; pp 15-39.
25. Sutton, J. M.; Clarke, O. J.; Fernandez, N.; Boyle, R. W. Bioconjugate Chem. 2002, 13, 249-263
26. Ethirajan, M.; Chen, Y.; Joshi, P.; Pandey, R. K. Chem. Soc. Rev. 2011, 40, 340-362
27. Singh, S.; Aggarwal, A.; Thompson, S.; Tomé, J. P. C.; Zhu, X.; Samaroo, D.; Vinodu, M.; Gao, R.; Drain, C. M. Bioconjugate Chem. 2010, 21, 2136-2146
28. Cao, W.; Ng, K. K.; Corbin, I.; Zhang, Z.; Ding, L.; Chen, J.; Zheng, G. Bioconjugate Chem. 2009, 20, 2023-2031
29. Kee, H. L.; Diers, J. R.; Ptaszek, M.; Muthiah, C.; Fan, D.; Lindsey, J. S.; Bocian, D. F.; Holten, D. Photochem. Photobiol. 2009, 85, 909-920
30. Kee, H. L.; Nothdurft, R.; Muthiah, C.; Diers, J. R.; Fan, D.; Ptaszek, M.; Bocian, D. F.; Lindsey, J. S.; Culver, J. P.; Holten, D. Photochem. Photobiol. 2008, 84, 1061-1072
31. Akers, W.; Lesage, F.; Holten, D.; Achilefu, S. Mol. Imaging 2007, 6, 237-246
32. Frangioni, J. V. Curr. Opin. Chem. Biol. 2003, 7, 626-634
33. Licha, K. Top. Curr. Chem. 2002, 222, 1-29
34. Mroz, P.; Huang, Y.-Y.; Szokalska, A.; Zhiyentayev, T.; Janjua, S.; Nifli, A.-P.; Sherwood, M. E.; Ruzié, C.; Borbas, K. E.; Fan, D.; Krayer, M.; Balasubramanian, T.; Yang, E.; Kee, H. L.; Kirmaier, C.; Diers, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S.; Hamblin, M. R. FASEB J. 2010, 24, 3160-3170
35. Huang, Y.-Y.; Mroz, P.; Zhiyentayev, T.; Sharma, S. K.; Balasubramanian, T.; Ruzié, C.; Krayer, M.; Fan, D.; Borbas, K. E.; Yang, E.; Kee, H. L.; Kirmaier, C.; Diers, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S.; Hamblin, M. R. J. Med. Chem. 2010, 53, 4018-4027
36. Huang, L.; Huang, Y.-Y.; Mroz, P.; Tegos, G. P.; Zhiyentayev, T.; Sharma, S. K.; Lu, Z.; Balasubramanian, T.; Krayer, M.; Ruzié, C.; Yang, E.; Kee, H. L.; Kirmaier, C.; Diers, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S.; Hamblin, M. R. Antimicrob. Agents Chemother. 2010, 54, 3834-3841
37. O'Connor, A. E.; Gallagher, W. M.; Byrne, A. T. Photochem. Photobiol. 2009, 85, 1053-1074
38. Brandis, A. S.; Salomon, Y.; Scherz, A. In Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications; Grimm, B.; Porra, R. J.; Rüdiger, W.; Scheer, H., Eds.; Springer: Dordrecht, The Netherlands, 2006; pp 485-494.
39. Nyman, E. S.; Hynninen, P. H. J. Photochem. Photobiol. B: Biol. 2004, 73, 1-28
40. Bonnett, R. Chemical Aspects of Photodynamic Therapy; Gordon and Breach Science Publishers: Amsterdam, 2000.
41. Davis, N. K. S.; Thompson, A. L.; Anderson, H. L. J. Am. Chem. Soc. 2011, 133, 30-31
42. Ikeda, S.; Toganoh, M.; Easwaramoorthi, S.; Lim, J. M.; Kim, D.; Furuta, H. J. Org. Chem. 2010, 75, 8637-8649
43. Kim, H.-J.; Lindsey, J. S. J. Org. Chem. 2005, 70, 5475-5486
44. Fan, D.; Taniguchi, M.; Lindsey, J. S. J. Org. Chem. 2007, 72, 5350-5357
45. McDowell, B. E. Ph.D. thesis, North Carolina State University, 2007.
46. Taniguchi, M.; Cramer, D. L.; Bhise, A. D.; Kee, H. L.; Bocian, D. F.; Holten, D.; Lindsey, J. S. New J. Chem. 2008, 32, 947-958
47. Borbas, K. E.; Ruzié, C.; Lindsey, J. S. Org. Lett. 2008, 10, 1931-1934
48. Ruzié, C.; Krayer, M.; Balasubramanian, T.; Lindsey, J. S. J. Org. Chem. 2008, 73, 5806-5820
49. Krayer, M.; Ptaszek, M.; Kim, H.-J.; Meneely, K. R.; Fan, D.; Secor, K.; Lindsey, J. S. J. Org. Chem. 2010, 75, 1016-1039
50. Krayer, M.; Yang, E.; Diers, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. New J. Chem. 2011, 35, 587-601
51. Kee, H. L.; Bhaumik, J.; Diers, J. R.; Mroz, P.; Hamblin, M. R.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Photochem. Photobiol. A: Chem. 2008, 200, 346-355
52. Seybold, P. G.; Gouterman, M. J. Mol. Spectrosc. 1969, 31, 1-13
53. Gradyushko, A. T.; Sevchenko, A. N.; Solovyov, K. N.; Tsvirko, M. P. Photochem. Photobiol. 1970, 11, 387-400
54. Weber, G.; Teale, F. W. J. Trans. Faraday Soc. 1957, 53, 646-655
55. Kee, H. L.; Kirmaier, C.; Yu, L.; Thamyongkit, P.; Youngblood, W. J.; Calder, M. E.; Ramos, L.; Noll, B. C.; Bocian, D. F.; Scheidt, W. R.; Birge, R. R.; Lindsey, J. S.; Holten, D. J. Phys. Chem. B 2005, 109, 20433-20443
56. Except for molecular mechanics and semi-empirical models, the calculation methods used in Spartan have been documented in: Shao, Y.; Molnar, L. F.; Jung, Y.; Kussmann, J.; Ochsenfeld, C.; Brown, S. T.; Gilbert, A. T. B.; Slipchenko, L. V.; Levchenko, S. V.; O'Neill, D. P. Phys. Chem. Chem. Phys. 2006, 8, 3172-3191
57. Smith, J. H. C.; Benitez, A. In Modern Methods of Plant Analysis; Paech, K.; Tracey, M. V., Eds.; Springer-Verlag: Berlin, 1955; Vol. IV, pp 142-196.
58. Holten, D.; Gouterman, M.; Parson, W. W.; Windsor, M. W.; Rockley, M. G. Photochem. Photobiol. 1976, 23, 415-423
59. Birks, J. B. Photophysics of Aromatic Molecules; Wiley-Interscience: London, 1970; pp 140-192.
60. Ptaszek, M.; Kee, H. L.; Muthiah, C.; Nothdurft, R.; Akers, W.; Achilefu, S.; Culver, J. P.; Holten, D. Proc. SPIE 2010, 7576, 75760E1-11
61. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 3, pp 1-165.
62. Gouterman, M. J. Mol. Spectrosc. 1961, 6, 138-163
63. Gouterman, M. J. Chem. Phys. 1959, 30, 1139-1161
64. Kee, H. L.; Kirmaier, C.; Tang, Q.; Diers, J. R.; Muthiah, C.; Taniguchi, M.; Laha, J. K.; Ptaszek, M.; Lindsey, J. S.; Bocian, D. F.; Holten, D. Photochem. Photobiol. 2007, 83, 1110-1124
65. Kee, H. L.; Kirmaier, C.; Tang, Q.; Diers, J. R.; Muthiah, C.; Taniguchi, M.; Laha, J. K.; Ptaszek, M.; Lindsey, J. S.; Bocian, D. F.; Holten, D. Photochem. Photobiol. 2007, 83, 1125-1143
66. Mass, O.; Ptaszek, M.; Taniguchi, M.; Diers, J. R.; Kee, H. L.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Org. Chem. 2009, 74, 5276-5289
67. Linnanto, J.; Korppi-Tommola, J. Phys. Chem. Chem. Phys. 2006, 8, 663-687
68. Petit, L.; Quartarolo, A.; Adamo, C.; Russo, N. J. Phys. Chem. B 2006, 110, 2398-2404
69. Petke, J. D.; Maggiora, G. M.; Shipman, L. L.; Christoffersen, R. E. Photochem. Photobiol. 1980, 32, 399-414
70. Weiss, C., Jr. J. Mol. Spectrosc. 1972, 44, 37-80
71. Yang, S. I.; Seth, J.; Strachan, J.-P.; Gentemann, S.; Kim, D.; Holten, D.; Lindsey, J. S.; Bocian, D. F. J. Porphyrins Phthalocyanines 1999, 3, 117-147
72. Kikuchi, K.; Kurabayashi, Y.; Kokubun, H.; Kaizu, Y.; Kobayashi, H. J. Photochem. Photobiol. A: Chem. 1988, 45, 261-263
73. Kajii, Y.; Obi, K.; Tanaka, I.; Tobita, S. Chem. Phys. Lett. 1984, 111, 347-349
74. Bonnett, R.; McGarvey, D. J.; Harriman, A.; Land, E. J.; Truscott, T. G.; Winfield, U.-J. Photochem. Photobiol. 1988, 48, 271-276