The effects of substituents and solvents on the ground-state π-electronic structure and electronic absorption spectra of a series of model merocyanine dyes and their theoretical interpretation

Chemistry - A European Journal

Volumn 18, Issue 26, 2012, Pages 8140-8149

  Mustroph, Heinz ^a   Reiner, Knut ^a   Senns, Bianca ^a   Mistol, Jürgen ^a   Ernst, Steffen ^a   Keil, Dietmar ^a   Hennig, Lothar ^b  

^a FEW Chemicals GmbH   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

cyanine limit; electronic structure; merocyanine; NMR spectroscopy; vibronic transitions

Indexed keywords

BOND ORDERS; C ATOMS; COUPLING CONSTANTS; CYANINE LIMIT; ELECTRONIC ABSORPTION SPECTRA; ELECTRONIC EXCITED STATE; ELECTRONIC GROUND STATE; ELECTRONIC SPECTRUM; FINE STRUCTURES; FRANCK-CONDON PRINCIPLE; MEROCYANINE; MEROCYANINE DYE; MODEL-BASED OPC; POLYMETHINE; POSITIVE CHARGES; TOTALLY SYMMETRIC; TWO-STATE; VALENCE BONDS; VIBRATIONAL QUANTUM NUMBER; VIBRATIONAL STATE; VIBRONIC TRANSITION;

ELECTRONIC STRUCTURE; GROUND STATE; MOLECULAR SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY;

SOLVENTS;

EID: 84862513709     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101830     Document Type: Article

References (59)

1. L. G. S. Brooker, G. H. Keyes, R. H. Sprague, R. H. VanDyke, E. VanLare, G. VanZandt, F. L. White, J. Am. Chem. Soc. 1951, 73, 5326-5332.
2. L. G. S. Brooker, in The Theory of the Photographic Process, 3rd revised ed., (Eds.: C. E. K. Mees, T. H. James,) Macmillan, New York, 1966, pp. 198-232.
3. G. Bach, S. Daehne in Second Supplements to the 2nd revised Edition of, Rodd's Chemistry of Carbon Compounds, Vol. IV B (Ed.:, M. Sainsbury,), Elsevier, Amsterdam, 1997, pp. 383-481.
4. S. Fujita, Organic Chemistry in Photography, Springer, Berlin, 2004.
5. A. Mishra, M. K. R. Fischer, P. Bäuerle, Angew. Chem. 2009, 121, 2510-2536
6. Angew. Chem. Int. Ed. 2009, 48, 2474-2499.
7. B. Strehmel, V. Strehmel, in Advances in Photochemistry, Vol. 29 (Eds.:, D. C. Neckers, W. S. Jenks, T. Wolff,), Wiley, Hoboken, 2007, pp. 111-341
8. G. S. He, L.-S. Tan, Q. Zheng, P. N. Prasad, Chem. Rev. 2008, 108, 1245-1330.
9. F. Würthner, R. Wortmann, K. Meerholz, ChemPhysChem 2002, 3, 17-31.
10. H. Mustroph, M. Stollenwerk, V. Bressau, Angew. Chem. 2006, 118, 2068-2087
11. Angew. Chem. Int. Ed. 2006, 45, 2016-2035
12. M. Emmelius, G. Pawlowski, H. W. Vollmann, Angew. Chem. 1989, 101, 1475-1502
13. Angew. Chem. Int. Ed. Engl. 1989, 28, 1445-1471.
14. M. Wainwright, Color. Technol. 2010, 126, 115-126
15. S. A. Gorman, S. B. Brown, J. Griffiths, J. Environ. Pathol. Toxicol. Oncol. 2006, 25, 79-108
16. R. R. Allison, G. H. Downie, R. Cuenca, X.-H. Hu, C. J. H. Childs, C. H. Sibata, Photodiagnosis and Photodynamic Therapy 2004, 1, 27-42.
17. G. Qian, Z. Y. Wang, Chem. Asian J. 2010, 5, 1006-1029
18. J. Griffiths, Chimia 1991, 45, 304-307.
19. L. G. S. Brooker, G. H. Keyes, R. H. Sprague, R. H. VanDyke, E. VanLare, G. VanZandt, F. L. White, H. W. J. Cressman, S. G. Dent, J. Am. Chem. Soc. 1951, 73, 5332-5350
20. L. G. S. Brooker, G. H. Keyes, D. W. Heseltine, J. Am. Chem. Soc. 1951, 73, 5350-5356.
21. L. G. S. Brooker, Experienta, Supplementum II 1955, 229-257.
22. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3 rd ed., Wiley-VCH, Weinheim, 2003, pp. 62-65.
23. J. N. Murrell, The Theory of the Electronic Spectra of Organic Molecules, Methuen, London, Wiley, New York, 1963, pp. 86.
24. S. R. Marder, J. W. Perry, B. G. Tiemann, C. B. Gorman, S. Gilmour, S. L. Biddle, G. Bourhill, J. Am. Chem. Soc. 1993, 115, 2524-2526
25. S. R. Marder, C. B. Gorman, B. G. Tiemann, L.-T. Cheng, J. Am. Chem. Soc. 1993, 115, 3006-3007
26. C. B. Gorman, S. R. Marder, Proc. Natl. Acad. Sci. USA 1993, 90, 11297-11301
27. S. R. Marder, J. W. Perry, G. Bourhill, C. B. Gorman, B. G. Tiemann, K. Mansour, Science 1993, 261, 186-189
28. G. Bourhill, J.-L. Brédas, L.-T. Cheng, S. R. Marder, F. Meyers, J. W. Perry, B. Tiemann, J. Am. Chem. Soc. 1994, 116, 2619-2620.
29. S. Dähne, Chimia 1991, 45, 288-296
30. S. Dähne, Science 1978, 199, 1163-1167.
31. H. Mustroph, J. Mistol, B. Senns, D. Keil, M. Findeisen, L. Hennig, Angew. Chem. 2009, 121, 8930-8933
32. Angew. Chem. Int. Ed. 2009, 48, 8773-8775.
33. A. V. Kulinich, A. A. Ishchenko, U. M. Groth, Spectrochim. Acta Part A 2007, 68, 6-14
34. A. V. Kulinich, N. A. Derevyanko, A. A. Ishchenko, Russ. Chem. Bull. 2005, 54, 2820-2830.
35. R. S. Mulliken, J. Am. Chem. Soc. 1952, 74, 811-824.
36. D. Lu, G. Chen, J. W. Perry, W. A. Goddard, J. Am. Chem. Soc. 1994, 116, 10679-10685
37. S. Ohira, J. M. Hales, K. J. Thorley, H. L. Anderson, J. W. Perry, J.-L. Brédas, J. Am. Chem. Soc. 2009, 131, 6099-6101.
38. R. Radeglia, G. Engelhardt, E. Lippmaa, T. Pehk, K.-D. Nolte, S. Dähne, Org. Magn. Res. 1972, 4, 571-576
39. R. Radeglia, J. Prakt. Chem. 1973, 315, 1121-1130
40. W. Grahn, Tetrahedron 1976, 32, 1931-1939
41. P. M. Henrichs, J. Chem. Soc. Perkin Trans. 2 1976, 542-547
42. G. Ponterini, F. Momicchioli, Chem. Phys. 1991, 151, 111-126
43. J. O. Morley, R. M. Morley, R. Docherty, M. H. Charlton, J. Am. Chem. Soc. 1997, 119, 10192-10202
44. J. O. Morley, R. M. Morley, A. L. Fitton, J. Am. Chem. Soc. 1998, 120, 11479-11488
45. A. Abbotto, L. Beverina, S. Bradamante, A. Facchetti, C. Klein, G. A. Pagani, M. Redi-Abshiro, R. Wortmann, Chem. Eur. J. 2003, 9, 1991-2007.
46. H. Mustroph, K. Reiner, J. Mistol, S. Ernst, D. Keil, L. Hennig, ChemPhysChem 2009, 10, 835-840.
47. L. Pauling, Proc. Natl. Acad. Sci. USA 1939, 25, 577-582
48. T. Förster, Z. Phys. Chem. Abt. B 1940, 47, 245-268
49. K. F. Herzfeld, J. Chem. Phys. 1942, 10, 508-520
50. A. L. Sklar, J. Chem. Phys. 1942, 10, 521-531
51. K. F. Herzfeld, A. L. Sklar, Rev. Mod. Phys. 1942, 14, 294-302.
52. G. Scheibe, W. Seiffert, G. Hohlneicher, C. Jutz, H. J. Springer, Tetrahedron Lett. 1966, 7, 5053-5059
53. G. Scheibe, in Optische Anregung organischer Systeme (Ed.:, W. Jung,), Verlag Chemie, Weinheim, 1966, pp. 109-159
54. G. Scheibe, E. Daltrozzo, O. Wörz, J. Heiss, Z. Phys. Chem. (Muenchen Ger.) 1969, 64, 97-114.
55. R. Radeglia, S. Dähne, J. Mol. Struct. 1970, 5, 399-411
56. M. Wähnert, S. Dähne, R. Radeglia, M. A. Alperovich, I. I. Levkoev, Adv. Mol. Relax. Processes 1977, 11, 263-282.
57. M. Blanchard-Desce, V. Alain, P. V. Bedworth, S. R. Marder, A. Fort, C. Runser, M. Barzoukas, S. Lebus, R. Wortmann, Chem. Eur. J. 1997, 3, 1091-1104.
58. E. U. Condon, Phys. Rev. 1928, 32, 858-872
59. H. Mustroph, S. Ernst, Chem. Unserer Zeit 2011, 45, 256-269.