On the nature of some biradicaloid and antiaromatic Vis/NIR-chromophores

Journal of Physical Organic Chemistry

Volumn 23, Issue 12, 2010, Pages 1137-1145

  Fabian, Jürgen ^a   Peichert, Rasmus ^b  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b NONE   (Germany)

Author keywords

antiaromatic cyclopentadienylium dyes; biradicaloid oxyallyl dyes; electron density difference maps; excitation energies; time dependent density functional theory

Indexed keywords

ABSORPTION WAVELENGTHS; ACCEPTOR GROUPS; AMINO GROUP; ANTIAROMATIC CYCLOPENTADIENYLIUM DYES; ARYL SUBSTITUENTS; BIRADICALOID OXYALLYL DYES; BIRADICALOID SPECIES; DONOR-ACCEPTOR COMPOUNDS; ELECTRON DENSITIES; ELECTRON DENSITY DIFFERENCE MAPS; ELECTRONIC TRANSITION; EXPECTATION VALUES; EXPERIMENTAL STUDIES; LONG WAVELENGTH; LOW ENERGIES; MULTI REFERENCE; NEAR INFRARED; NUCLEUS-INDEPENDENT CHEMICAL SHIFTS; PARENT COMPOUNDS; POLYMETHINE; POLYMETHINE DYE; SINGLET-TRIPLET SPLITTING; SPECTRAL EXCITATION; SPIN PROPERTIES; SQUARAINES; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TITLE COMPOUNDS;

ABSORPTION; AZO DYES; CARRIER CONCENTRATION; CHARGE TRANSFER; CHROMOPHORES; ELECTRON DENSITY MEASUREMENT; ELECTRONS; EXCITATION ENERGY; ORGANIC POLYMERS; SUBSTITUTION REACTIONS;

DENSITY FUNCTIONAL THEORY;

EID: 78649889218     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1684     Document Type: Article

References (56)

1. J. Griffiths, Chimia 1991, 45, 304-307.
2. J. Griffiths, Chem. Unserer Zeit 1993, 27, 21-31.
3. S. Dähne, U. Resch-Genger, O. S. Wolfbeis, (Eds) Near-infrared Dyes for High Technology Applications, NATO ASI Ser., Ser. 3, Vol. 52, Kluwer Academic Publishers, Dortrecht, 1998.
4. S.-H. Kim, Functional Dyes, Elsevier, Amsterdam, 2006.
5. J. Fabian, H. Nakazumi, M. Matsuoka, Chem. Rev. 1992, 92, 1197-1226.
6. J. Fabian, R. Zahradník, Angew. Chem. 1989, 101, 693-710.
7. J. Fabian, R. Zahradník, Angew. Chem. Int. Ed. 1989, 28, 677-828.
8. The term biradical is synonymous with diradical that is no longer recommended by IUPAC, Pure Appl. Chem. 1996, 68, 2223-2286.
9. Ch. Prabhakar, G. K. Chatanya, S. Sitha, K. Bhanuprakash, V. J. Rao, J. Phys. Chem. A 2005, 109, 2614-2622.
10. Ch. Prabhakar, K. Yesudas, G. K. Chaitanya, S. Sitha, K. Bhanuprakash, V. J. Rao, J. Phys. Chem. A 2005, 109, 8604-8616.
11. K. Srinivas, Ch. Prabhakar, C. L. Devi, K. Yesudas, K. Bhanuprakash, V. J. Rao, J. Phys. Chem. A 2007, 111, 3378-3386.
12. K. Yesudas, K. Bhanuprakash, J. Phys. Chem. A 2007, 111, 1943-1952.
13. A. Thomas, K. Srinavas, Ch. Prabhakar, K. Bhanuprakash, J. V. Rao, Chem. Phys. Lett. 2008, 454, 36-41.
14. A. L. Puyad, Ch. Prabhakar, K. K. Yesudas, K. Bhanuprakash, V. J. Rao, J. Mol. Struct. (Theochem) 2009, 904, 1-6.
15. The nomenclature of the oxyallyl compounds is not consistent. The name squaraine was early coined by A.H. Schmidt (Synthesis, 1980, 961-994) for derivatives of the squaric acid substituted in 1,3-position. The analogous names for the 1,3- substituted five- and six-membered rings may be croconaine and rhodizonaine. Names such as squarate (sqarylium), croconate, and rhodizonate are also used. They suggest salt-like structures. The systematical naming of compounds based on biradical or ylid (mesoionic) structures is not always practicable.
16. R. W. Bigelow, H. J. Freund, Chem. Phys. 1986, 159-174.
17. K. Y. Law, J. Phys. Chem. 1987, 91, 5184-5193.
18. M. Tian, S. Tatsuura, M. Furuki, Y. Sato, I. Iwas, L. S. Pu, J. Am. Chem. Soc. 2003, 125, 348-349.
19. H. Langhals, Angew. Chem. 2003, 115, 4422-4424.
20. H. Langhals, Angew. Chem. Int. Ed. 2003, 42, 4286-4288.
21. R. Mayer, J. Fabian, H. Viola, L. Jakisch, Phosphorus Sulfur 1987, 31, 109-122.
22. D. Barrilier, Phosphorus Sulfur 1980, 8, 79-85.
23. A. Hordvik, K. Jynge, I. Pedersen, Acta Chem. Scand. Ser. A 1981, 35, 607-616.
24. M. Mann, J. Fabian, J. Phys. Org. Chem. 1995, 8, 536-544.
25. S. Dähne, Z. Chem. 1965, 5, 441-451.
26. S. Dähne, Chimia 1991, 45, 288-296 and references cited therein.
27. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH, Weinheim, 2000.
28. M. C. Zerner, Semiempirical molecular orbital methods, in Reviews in Computational Chemistry, (Eds:, K. B. Lipkowitz, D. B. Boyd,), Vol. 2, Wiley-VCH, New Jersey, 1991, 313-365 and references cited therein.
29. J. Fabian, J. Signalaufzeichnungsmaterialien 1978, 6, 307-321.
30. J. Fabian, A. Mehlhorn, F. Fratev, Int. J. Quantum Chem. 1980, 17, 235-253.
31. D. Jacqemin, E. A. Perpete, I. Ciofini, C. Adamo, Acc. Chem. Res. 2009, 42, 326-334 and references cited therein.
32. J. Fabian, Dyes Pigm. 2010, 84, 36-53 and references cited therein.
33. J. Gräfenstein, D. Cremer, Mol. Phys. 2001, 99, 981-989.
34. J. Wirz, Pure Appl. Chem. 1984, 56, 1289-1300.
35. P. von Ragué Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
36. V. Barone, C. Adamo, J. Chem. Phys. 1999, 110, 6158-6170.
37. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery,Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh, PA, 2003.
38. F. Neese, J. Chem. Phys. 2003, 119, 9428-9443.
39. An Ab initio, DFT and semiempirical electronic structure package, program version 2.6, revision 35. Developed by Frank Neese, Universität Bonn, 2008, ORCA Website
40. ArgusLab Website
41. J. Dale, O. I. Eriksen, Acta Chem. Scand. Ser. B 1988, 42, 242-246.
42. D. González, O. Neilands, M. C. Rezende, J. Perkin Trans. 2 1999, 713-717.
43. A. Mehlhorn, J. Fabian, N. Tyutyulkov, G. Olbrich, F. Dietz, J. Prakt. Chem. 1986, 328, 603-611.
44. F. Dietz, N. Tyutyulkov, M. Rabinovitz, J. Chem. Soc. Perkin Trans. 2 1993, 1972-1999.
45. J. Fabian, H. Hartmann, Light Absorption of Organic Colorants. Theoretical Treatment and Empirical Rules, Springer, Berlin, 1980 and references cited therein.
46. R. Gompper, A. Beck, T. Gessner, K. Hartmann, D. Heindl, K. Polborn, R. Klinger, K. Yokogawa, Near-infrared Dyes for High Technology Applications (Eds:, S. Dähne, U. Resch-Genger, O. S. Wolfbeis,), Kluwer Academic Publishers, Dordrecht, 1994, pp. 363-383.
47. T. Hutton, Polyhedron 1987, 6, 13-23.
48. G. Röbisch, R. Nöske, Dyes Pigm. 1987, 8, 165-177.
49. T. Schönherr, R. Linder, U. R. Schmid, Int. J. Quantum Chem. 2002, 86, 90-99.
50. B. A. Hess, Jr., L. Smentek, Eur. J. Org. Chem. 1999, 3363-3367.
51. M. B. Coolidge, K. Yamashita, K. Morokuma, W. Th. Borden, J. Am. Chem. Soc. 1990, 112, 1751-1754.
52. Ch. A. Schalley, S. Blanksby, J. N. Harvey, D. Schröder, W. Zummack, J. H. Bowie, H. Schwarz, Eur. J. Org. Chem. 1998, 987-1009.
53. J. Shen, T. Fang, S. Li, Y. Jiang, J. Phys. Chem. Ser. A 2008, 112, 1258-12525.
54. O. Kikuchi, H. Nagata, K. Morihashi, Theochem 1985, 25, 261-268.
55. T. Furuhata, W. Ando, Tetrahedron Lett. 1986, 27, 4035-4038.
56. S. Nakatsuji, H. Nakazumi, H. Fukuma, T. Yahiro, K. Nakashima, M. Iyoda, S. Akiyama, J. Chem. Soc. Chem. Commun. 1990, 489-491.