Vertically π-expanded coumarin - synthesis via the Scholl reaction and photophysical properties

Physical Chemistry Chemical Physics

Volumn 16, Issue 34, 2014, Pages 18268-18275

  Tasior, Mariusz ^a   Deperasińska, Irena ^b   Morawska, Karolina ^c   Banasiewicz, Marzena ^b   Vakuliuk, Olena ^a,c   Kozankiewicz, Bolesław ^b   Gryko, Daniel T ^a,c  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b INSTITUTE OF PHYSICS   (Poland)

^c WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN; COUMARIN DERIVATIVE; NAPHTHALENE; NAPHTHALENE DERIVATIVE;

CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; LIGHT; MATERIALS TESTING; RADIATION RESPONSE; SYNTHESIS;

COMPUTER SIMULATION; COUMARINS; LIGHT; MATERIALS TESTING; MODELS, CHEMICAL; MODELS, MOLECULAR; NAPHTHALENES;

EID: 84905842099     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/c4cp02003k     Document Type: Article

References (79)

1. R. O. Kennedy, and R. D. Thornes, Coumarins: Biology, Applications and Mode of Action, Wiley and Sons, Chichester, 1997
2. M. A. Al-Haiza, M. S. Mustafa, M. Y. El-Kady Molecules, 2003, 8, 275-286
3. Y. Takeuchi, L. Xie, L. M. Cosentino, K. H. Lee Bioorg. Med. Chem. Lett., 1997, 7, 2573-2578
4. M. A. Musa, M. Omar, F. Khan, J. S. Cooperwood Lett. Drug Des. Discovery, 2009, 6, 133-138
5. H. Zhao, N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, G. W. Milne, Y. Pommier, T. R. Burke J. Med. Chem., 1997, 40, 242-249
6. R. M. Christie, K. M. Morgan, M. S. Islam Dyes Pigm., 2008, 76, 741-747
7. X. Luo, X. Naiyun, L. Cheng, D. Huang Dyes Pigm., 2001, 51, 153-159
8. M.-S. Peng, J. Cai Dyes Pigm., 2008, 79, 270-272
9. C. Murata, T. Masuda, Y. Kamochi, K. Todoroki, H. Yoshida, H. Nohta, M. Yamaguchi, A. Takadate Chem. Pharm. Bull., 2005, 53, 750-758
10. A. Elangovan, J.-H. Lin, S.-W. Yang, H.-Y. Hsu, T.-I. Ho J. Org. Chem., 2004, 69, 8086-8092
11. A. R. S. Koefod, K. R. Mann Inorg. Chem., 1989, 28, 2285-2290
12. B. S. Tasch, C. Brandstatter, F. Meghdadi, G. Leising, G. Froyer, L. Athouel Adv. Mater., 1997, 9, 33-36
13. A. Adronov, S. L. Gilat, J. M. J. Fréchet, K. Ohta, F. V. R. Neuwahl, G. R. Fleming J. Am. Chem. Soc., 2000, 122, 1175-1185
14. M. Tasior, D. T. Gryko, D. Pielacińska, A. Zanelli, L. Flamigni Chem. - Asian J., 2010, 5, 130-140
15. J. M. Serin, W. Brousmiche, M. T. Fréchet Chem. Commun., 2002, 2605-2607
16. C. A. E. Siegrist, H. Hefti, H. R. Mayer, E. Schmidt Rev. Prog. Color. Relat. Top., 1987, 17, 39-55
17. S. Uchiyama, K. Takehira, T. Yoshihara, S. Tobita, T. Ohwada Org. Lett., 2006, 8, 5869-5872
18. T. Hirano, K. Hiromoto, H. Kagechika Org. Lett., 2007, 9, 1315-1318
19. D. J. Yee, V. Balsanek, D. Sames J. Am. Chem. Soc., 2004, 126, 2282-2283
20. K. Sivakumar, F. Xie, B. M. Cash, S. Lung, H. N. Barnhill, Q. A. Wang Org. Lett., 2004, 6, 4603-4606
21. M.-S. Schiedel, C. A. Briehn, P. Bäuerle Angew. Chem., Int. Ed., 2001, 40, 4677-4680
22. M. Min, S. Hong Chem. Commun., 2012, 48, 9613-9615
23. Z. Shao, L. Xu, L. Wang, H. Wei, J. Xiao Org. Biomol. Chem., 2014, 12, 2185-2188
24. J. Ferguson, F. Zeng, H. Alper Org. Lett., 2012, 14, 5602-5605
25. M. K. Węcławski, M. Tasior, T. Hammann, P. J. Cywiński, D. T. Gryko Chem. Commun., 2014, 50, 9105-9108
26. T. Högberg, M. Vora, S. D. Drake, L. A. Mitscher, D. T. W. Chu Acta Chem. Scand. Ser. B, 1984, 38, 359-366
27. Y. M. Poronik, M. P. Shandura, Y. P. Kovtun Chem. Heterocycl. Compd., 2006, 42, 410-411
28. M. Tasior, R. Voloshchuk, Y. M. Poronik, T. Rowicki, D. T. Gryko J. Porphyrins Phthalocyanines, 2011, 15, 1011-1023
29. O. S. Wolfbeis Monatsh. Chem., 1978, 109, 1413-1421
30. P. L. Nandaluru, G. J. Bodwell Org. Lett., 2012, 14, 310.
31. I. Kim, D. Kim, S. Sambasivan, K. H. Ahn Asian J. Org. Chem., 2012, 1, 60-64
32. D. Kim, S. Singha, T. Wang, E. Seo, J. H. Lee, S.-J. Lee, K. Kim, K. H. Ahn Chem. Commun., 2012, 48, 10243-10245
33. S. A. Glover, S. L. Golding, A. Goosen, C. W. McCleland J. Chem. Soc., Perkin Trans. 1, 1981, 842-848
34. S. Abdel-Baky, C. Sotiriou-Leventis, R. W. Giese Tetrahedron, 1991, 47, 5667-5672
35. E. Lee-Ruff, H. Kruk, M. Katz J. Org. Chem., 1984, 49, 553-555
36. M. D. Markey, Y. Fu, T. R. Kelly Org. Lett., 2007, 9, 3255-3257
37. O. Zinke Monatsh. Chem., 1953, 84, 1131-1139
38. T. Lu, B. Tomczuk, L. V. LaFrance, T. P. Markotna, J. J. M. Sanchez, V. J. Marder, C. U’Prichard, B. M. Anaclerio, Z. Guo, W. Pan, and K. A. Leonard, U.S. Pat. Appl., 2007/0219233 A1, 2007
39. See the ESI for more details
40. N. M. O’Boyle, A. L. Tenderholt, K. M. Langner J. Comput. Chem., 2008, 29, 839-845
41. V. Barone, J. Bloino, M. Biczysko, F. Santoro J. Chem. Theory Comput., 2009, 5, 540-554
42. J. Bloino, M. Biczysko, F. Santoro, V. Barone J. Chem. Theory Comput., 2010, 6, 1256-1274
43. H. Pechmann, C. Duisberg Ber. Dtsch. Chem. Ges., 1883, 16, 2119.
44. S. Sethna, and R. Phadke, Organic Reactions, John Wiley & Sons Inc., 2004, pp. 1-58
45. D. Pillon Bull. Soc. Chim. Fr., 1955, 39-44
46. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire Chem. Rev., 2002, 102, 1359-1469
47. M. Grzybowski, K. Skonieczny, H. Butenschön, D. T. Gryko Angew. Chem., Int. Ed., 2013, 52, 9900.
48. E. Clar, W. Kelly, D. G. Stewart, J. W. Wright J. Chem. Soc., 1956, 2652-2656
49. C. Joblin, F. Salama, I. Allamandola J. Chem. Phys., 1999, 110, 7287-7297
50. I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, Academic Press, New York, 1971
51. J. N. Demas, G. A. Crosby J. Phys. Chem., 1971, 75, 991.
52. N. Nijegorodov, D. P. Winkoun Spectrochim. Acta, Part A, 1997, 53, 2013-2022
53. D. W. Fink, W. R. Koehler Anal. Chem., 1970, 42, 990-993
54. N. Nizomov, A. U. Kholov, A. A. Ishchenko, V. V. Ishchenko, V. P. Khilya J. Appl. Spectrosc., 2007, 74, 626.
55. C. M. Krauter, J. Möhring, T. Buckup, M. Pernpointner, M. Motzkus Phys. Chem. Chem. Phys., 2013, 15, 17846-17861
56. E. Gök J. Fluoresc., 2013, 23, 333-338
57. S. Sebastian, S. Sylvestre, D. Jayarajan, M. Amalanathan, K. Oudayakumar, T. Gnanapoongothai, T. Jayavarthanan Spectrochim. Acta, Part A, 2013, 101, 370-381
58. T. J. Brett, J. M. Alexander, J. J. Stezowski J. Chem. Soc., Perkin Trans. 1, 2000, 1095-1103
59. M. Pirotta, A. Renn, M. H. V. Werts, U. P. Wild Chem. Phys. Lett., 1996, 250, 576-582
60. J. J. Dekkers, G. Ph. Hoornweg, C. Maclean, N. H. Velthorst Chem. Phys., 1974, 5, 393-407
61. P. J. Walla, F. Jelezko, P. Tamarat, B Lounis, M. Orrit Chem. Phys., 1998, 233, 117-125
62. A. Nicolet, M. Kol’chenko, B. Kozankiewicz, M. Orrit J. Chem. Phys., 2006, 124, 164711.
63. E. B. Priestley, A. Haug J. Chem. Phys., 1968, 49, 622.
64. D. Jacquemin, E. A. Perpete, G. Scalmani, M. J. Frish, X. Assfeld, I. Ciofini, C. Adamo J. Chem. Phys., 2006, 125, 164324.
65. R. Graber, M. W. Grimes, A. Haug J. Chem. Phys., 1969, 50, 1623.
66. J. Seixas de Melo, P. F. Fernandes J. Mol. Struct., 2001, 565/566, 69-78
67. J. R. Johnson, K. D. Jordan, D. F. Plusquellic, D. W. Pratt J. Chem. Phys., 1990, 93, 2258-2273
68. T. Ebata, K. Kouyama, N. Mikami J. Chem. Phys., 2003, 119, 2947-2950
69. F. Lahmani, A. Dodd, E. Breheret, A. Zehnacker-Rentien Chem. Phys. Lett., 1994, 220, 235-242
70. H. Beens, and A. Weller, Organic Molecular Photophysics, ed. J. Birks, Wiley, London, 1976, p. 159; solvent effect p. 201
71. I. Deperasinska, J. Dresner THEOCHEM, 1998, 422, 205.
72. A. B. J. Parusel J. Photochem. Photobiol., B, 2000, 55, 188.
73. A. Makarewicz, A. Szemik-Hojniak, G. van der Zwan, I. Deperasinska J. Phys. Chem. A, 2009, 113, 3438-3446
74. S. Karabunarliev, M. Baumgarten, K. Müllen J. Phys. Chem. A, 1998, 102, 7029-7034
75. R. Srinivasan, J. S. Feenstra, S. T. Park, S. Xu, A. H. Zewail Science, 2005, 307, 558-563
76. A. Berces, M. Z. Zgierski, and D.-S. Yang, in Computational Molecular Spectroscopy, ed. P. Jensen and P. Bunker, John Wiley, Chichester, U.K., 2000, p. 119
77. I. Georgieva, N. Trendafilova, A. Aquino, H. Lischka J. Phys. Chem. A, 2005, 109, 11860-11869
78. J. R. Heldt, J. Heldt, M. Ston, H. A. Diehl Spectrochim. Acta, Part A, 1995, 51, 1549-1563
79. R. M. Hochstrasser Can. J. Chem., 1961, 39, 451-458