Solvatochromic fluorescent 2-substituted 3-ethynyl quinoxalines: Four-component synthesis, photophysical properties, and electronic structure

Journal of Organic Chemistry

Volumn 79, Issue 8, 2014, Pages 3296-3310

  Gers, Charlotte F ^a   Nordmann, Jan ^a   Kumru, Ceyda ^a   Frank, Walter ^a   Müller, Thomas J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUNDS; CHLORINE COMPOUNDS; FLUORESCENCE;

ELECTRON-RICH; OXALYL CHLORIDE; PHOTOPHYSICAL PROPERTIES; QUINOXALINES; SOLVATOCHROMIC; SOLVATOCHROMISMS; TERMINAL ALKYNE; TITLE COMPOUNDS;

ELECTRONIC STRUCTURE;

1,2 DICHLOROETHANE; 3 ETHYNYLQUINOXALINE DERIVATIVE; DICHLOROMETHANE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ALKYNYLATION; ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DIPOLE; ELECTROPHILICITY; GLYOXYLATION; HYDROGEN BOND; MECHANICAL TORSION; NUCLEOPHILICITY; QUANTUM YIELD; REACTION TIME; SOLUBILITY; STEPHENS CASTRO COUPLING; SYNTHESIS;

EID: 84899003761     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4025978     Document Type: Article

References (74)

1. Kelley, T. W.; Baude, P. F.; Gerlach, C.; Ender, D. E.; Muyres, D.; Haase, M. A.; Vogel, D. E.; Theiss, S. D. Chem. Mater. 2004, 16, 4413-4422
2. Forrest, S. R.; Thompson, M. E. Chem. Rev. 2007, 107, 923-925
3. Müller, T. J. J. In Functional Organic Materials. Syntheses, Strategies, and Applications; Müller, T. J. J.; Bunz, U. H. F., Eds.; Wiley: Weinheim, 2007; pp 179-223. For the concept of diversity oriented synthesis, see, e.g.
4. Burke, M. D.; Schreiber, S. L. Angew. Chem. 2004, 116, 48-60
5. Angew. Chem., Int. Ed. 2004, 43, 46-58.
6. Sunderhaus, J. D.; Martin, S. F. Chem. - Eur. J. 2009, 15, 1300-1308
7. Isambert, N.; Lavilla, R. Chem. - Eur. J. 2008, 14, 8444-8454
8. Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471-1499
9. Bonne, D.; Coquerel, Y.; Constantieux, T.; Rodriguez, J. Tetrahedron: Asymmetry 2010, 21, 1085-1109
10. Tietze, L. F. Chem. Rev. 1996, 96, 115-136
11. Coquerel, Y.; Boddaert, T.; Presset, M.; Mailhol, D.; Rodriguez, J. In Ideas in Chemistry and Molecular Sciences, Vol. 1, Advances in Synthetic Chemistry; Pignataro, B., Ed.; Wiley-VCH: Weinheim, 2010; Chapter 9, pp 187-202.
12. DSouza, D. M.; Müller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095-1108
13. Müller, T. J. J. Top. Heterocycl. Chem. 2010, 25, 25-94
14. Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304-322
15. Touré, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439-4486
16. Cordier, C.; Morton, D.; Murrison, S.; Nelson, A.; OLeary-Steele, C. Nat. Prod. Rep. 2008, 25, 719-737
17. Ishikura, M.; Abe, T.; Choshi, T.; Hibino, S. Nat. Prod. Rep. 2013, 30, 694-752
18. OHagan, D. Nat. Prod. Rep. 2000, 17, 435-446
19. Bay, S.; Villnow, T.; Ryseck, G.; Rai-Constapel, V.; Gilch, P.; Müller, T. J. J. ChemPlusChem 2013, 78, 137-141
20. Cinar, R.; Nordmann, J.; Dirksen, E.; Müller, T. J. J. Org. Biomol. Chem. 2013, 11, 2597-2604
21. Dostert, C.; Wanstrath, C.; Frank, W.; Müller, T. J. J. Chem. Commun. 2012, 48, 7271-7273
22. Meyer, T.; Ogermann, D.; Pankrath, A.; Kleinermanns, K.; Müller, T. J. J. J. Org. Chem. 2012, 77, 3704-3715
23. Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2002, 45, 5604-5606
24. Kim, Y. B.; Kim, Y. H.; Park, J. Y.; Kim, S. K. Bioorg. Med. Chem. Lett. 2004, 541-544
25. Amin, K. M.; Ismail, M. M. F.; Noaman, E.; Soliman, D. H.; Ammar, Y. A. Bioorg. Med. Chem. 2006, 14, 6917-6923
26. Woody, K. B.; Henry, E. M.; Jagtap, S.; Collard, D. M. Macromolecules 2011, 44, 9118-9124
27. Zhao, Q.; Li, R.-F.; Xing, S.-K.; Liu, X.-M.; Hu, T.-L.; Bu, X.-H. Inorg. Chem. 2011, 50, 10041-10046
28. Pan, Y.; Sheng, Z.; Ye, X.; Ao, Z.; Chu, G.; Dai, J.; Yu, S. J. Photochem. Photobiol. A 2005, 174, 98-105
29. Anguloa, G.; Dobkowskia, J.; Kapturkiewicza, A.; Maciolek, K. J. Photochem. Photobiol. A 2010, 213, 101-106
30. Schaffroth, M.; Lindner, B. D.; Vasilenko, V.; Rominger, F.; Bunz, U. H. F. J. Org. Chem. 2013, 78, 3142-3150
31. Rao, M. R.; Liao, C.-W.; Su, W.-L.; Sun, S.-S. J. Mater. Chem. C 2013, 1, 5491-5501
32. Pina, J.; Seixas de Melo, J.; Breusov, D.; Scherf, U. Phys. Chem. Chem. Phys. 2013, 15, 15204-15213
33. Kudo, K.; Momotake, A.; Kanna, Y.; Nishimuraa, Y.; Arai, T. Chem. Commun. 2011, 47, 3867-3869
34. Lin, T. C.; Chien, W.; Liu, C. Y.; Tsai, M.-Y.; Huang, Y.-J. Eur. J. Org. Chem. 2013, 4262-4269
35. Faust, R.; Weber, C. Tetrahedron 1997, 53, 14655-14670
36. Mitzel, F.; FitzGerald, S.; Beeby, A.; Faust, R. Chem. - Eur. J. 2003, 9, 1233-1241
37. Merkul, E.; Dohe, J.; Gers, C.; Rominger, F.; Müller, T. J. J. Angew. Chem. 2011, 123, 2023-2026
38. Angew. Chem., Int. Ed. 2011, 50, 2966-2969.
39. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470
40. Tohda, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1977, 777-778
41. Merkul, E.; Oeser, T.; Müller, T. J. J. Chem. - Eur. J. 2009, 15, 5006-5011
42. Chowdhury, C.; Kundu, N. G. Tetrahedron 1999, 55, 7011-7016
43. Wang, J.-X.; Wei, B.; Hu, Y.; Liu, Z.; Fu, Y. Synth. Commun. 2001, 31, 3527-3532
44. Boersch, C.; Merkul, E.; Müller, T. J. J. Angew. Chem. 2011, 123, 10632-10636
45. Angew. Chem., Int. Ed. 2011, 50, 10448-10452.
46. Mukherjee, A. K.; Margaretha, P.; Agosta, W. C. J. Org. Chem. 1996, 61, 3388-3391
47. François-Endelmond, C.; Carlin, T.; Thuery, P.; Loreau, O.; Taran, F. Org. Lett. 2010, 12, 40-42
48. Wu, Y.; Yao, W.; Pan, L.; Zhang, Y.; Ma, C. Org. Lett. 2010, 12, 640-643
49. Liu, Y.; Liu, M.; Guo, S.; Tu, H.; Zhou, Y.; Gao, H. Org. Lett. 2006, 8, 3445-3448
50. Bagley, M. C.; Dale, J. W.; Xiong, X.; Bower, J. Org. Lett. 2003, 5, 4421-4424
51. Ames, D. E.; Brohi, M. I. J. Chem. Soc., Perkin Trans. 1 1980, 1384-1389
52. Wang, W.; Shen, Y.; Meng, X.; Zhao, M.; Chen, Y.; Chen, B. Org. Lett. 2011, 4514-4517
53. Reichardt, C.; Welton, T. Solvents and Solvent Effects in Organic Chemistry, 4 th ed.; Wiley-VCH: Weinheim, 2011; pp 384-393.
54. Loving, G. S.; Sainlos, M.; Imperiali, B. Trends Biotechnol. 2010, 28, 73-83
55. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77
56. Boens, N.; Qin, W.; Basarić, N.; Hofkens, J.; Amelot, M.; Pouget, J.; Lefévre, J.-P.; Valeur, B.; Gratton, E.; vandeVen, M.; Silva, N. D., Jr.; Engelborghs, Y.; Willaert, K.; Sillen, A.; Rumbles, G.; Phillips, D.; Visser, A. J. W. G.; van Houk, A.; Lakowicz, J. R.; Malak, H.; Gryczynski, I.; Szabo, A. G.; Krajcarski, D. T.; Tamai, N.; Miura, A. Anal. Chem. 2007, 79, 2137-2149
57. Fery-Forgues, S.; Lavabre, D. J. Chem. Educ. 1999, 76, 1260-1264
58. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3 rd ed.; Springer: Berlin/Heidelberg, 2006; pp 213-216.
59. Lippert, E. Z. Elektrochem. 1957, 61, 962-975
60. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465-470
61. 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.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09 (Revision A.02), Gaussian, Inc., Wallingford, CT, 2009.
62. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
63. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
65. Kim, K.; Jordan, K. D. J. Phys. Chem. 1994, 98, 10089-10094
66. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
67. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654
68. Scalmani, G.; Frisch, M. J. J. Chem. Phys. 2010, 132, 114110
69. Yanai, T.; Tew, D.; Handy, N. Chem. Phys. Lett. 2004, 393, 51-57
70. Berezhkovski, A. M. Chem. Phys. 1992, 164, 331-339
71. Cammi, R.; Thomasi, J. Int. J. Quant. Chem.: Quant. Chem. Symp. 1995, 29, 465-474
72. Mennucci, B.; Cammi, R.; Tomasi, J. J. Chem. Phys. 1998, 109, 2798-2807
73. Li, X.-Y.; Fu, K.-X. J. Comput. Chem. 2004, 25, 500-509
74. Cammi, R.; Corni, S.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 2005, 122, 104513