Synthesis and fluorescence properties of 5,7-diphenylquinoline and 2,5,7-triphenylquinoline derived from m-terphenylamine

Molecules

Volumn 12, Issue 5, 2007, Pages 988-996

  Qi, Shujian ^a   Shi, Kehui ^a   Gao, Hongyin ^a   Liu, Qiancai ^a   Wang, Hong ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

2,5,7 triphenylquinoline; 5,7 diphenylquinoline; m terphenylamine; Skraup reaction; Synthesis

Indexed keywords

ANILINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; FLUORESCENCE; METHODOLOGY; SPECTROSCOPY; SYNTHESIS;

ANILINE COMPOUNDS; FLUORESCENCE; QUINOLINES; SPECTRUM ANALYSIS;

EID: 34249892223     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12050988     Document Type: Article

References (38)

1. Tang, C.W.; van Slyke, S.A. Organic electroluminescent diodes. Appl. Phys. Lett. 1987, 51, 913-915.
2. Burroughes, J.H.; Bradeley, D.C.; Brown, A.R.; Marks, R.N. Light-emitting diodes based on conjugated polymers. Nature 1990, 347, 539-541.
3. rd Edition; Addison Wesley Longman: Essex, U.K., 1997;
4. nd Edition; John Wiley & Sons, Inc.: Chichester, U.K., 2003.
5. Kushto, G.P.; Iizumi, Y.; Kido, J.; Kafafi, Z.H. A Matrix-Isolation Spectroscopic and Theoretical Investigation of Tris(8-hydroxyquinolinato) aluminum(III) and Tris(4-methyl-8-hydroxyquinolinato) aluminum(III). J. Phys. Chem. A. 2000, 104, 3670-3680.
6. Wu, X.-M.; Hua, Y.-L.; Wang, Z.-Q.; Zheng, J.-J.; Feng, X.-L.; Sun, Y.-Y. White organic light-emitting devices based on 2-(2-hydroxyphenyl)benzothiazole and its chelate metal complex. Chin. Phys. Lett. 2005, 22, 1797-1799.
7. (a) Morimoto, Y.; Matsuda, F.; Shirahama, H. Total synthesis of (±)-virantmycin and determination of its stereochemistry. Synlett. 1991, 3, 201-203;
8. (b) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. Methodologies for synthesis of heterocyclic compounds. J. Heterocycl. Chem. 1992, 29, 619-625;
9. (c) Michael, J.P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 1997, 14, 605-608.
10. (a) Markees, D.G.; Dewey, V.C.; Kidder, G.W. Antiprotozoal 4-aryloxy-2-aminoquinolines and related compounds. J. Med. Chem. 1970, 13, 324-326;
11. (b) Alhaider, A.A.; Abdelkader, M.A.; Lien, E.J. Design, synthesis and pharmacological activities of 2-substituted 4-phenylquinolines as potential antidepressant drugs. J. Med. Chem. 1985, 28, 1394-1398;
12. (c) Campbell, S.F.; Hardstone, J.D.; Palmer, M.J. 2,4-Diamino-6,7- dimethoxyquinoline derivatives as α 1-adrenoceptor antagonists and antihypertensive agents. J. Med. Chem. 1988, 31, 1031-1305.
13. Abegg, R. Amidochrysene. Ber. 1890, 23, 792-793.
14. Bamberger, E.; Burgdorf, C. Chrysene. Ber. 1890, 23, 2433-2446.
15. (a) Castro, A.; Martinez, A. Peripheral and binding site acetylcholinesterase inhibitors: implications in treatment of Alzheimer's disease. Mini-Rev. Med. Chem. 2001, 1, 267-272;
16. (b) Silman, I.; Sussman, J.L. Acetylcholinesterase: "classical" and "non-classical" functions and pharmacology. Curr. Opin. Pharmacol. 2005, 5, 293-302;
17. (c) Munoz-Torrero, D.; Camps, P. Dimeric and hybrid anti-Alzheimer drug candidates. Curr. Med. Chem. 2006, 13, 399-422.
18. (a) Denmark, S.E.; Venkatraman, S. On the Mechanism of the Skraup-Doebner-Von Miller Quinoline Synthesis. J. Org. Chem. 2006, 71, 1668-1676;
19. (b) Kamiguchi, S.; Takahashi, I.; Kurokawa, H.; Miura, H.; Chihara, T. Vapor-phase synthesis of 1,2-dihydro-2,2,4-trimethylquinolines from anilines and acetone over group 5-7 metal halide clusters as catalysts. Appl. Catal., A. 2006, 309, 70-75;
20. (c) Wu, Y.-C.; Liu, L.; Li, H.-J.; Wang, D.; Chen, Y.-J. Skraup-Doebner-Von Miller Quinoline Synthesis Revisited: Reversal of the Regio-chemistry for γ-Aryl-β,γ-unsaturated α-Ketoesters. J. Org. Chem. 2006, 71, 6592-6595;
21. (d) Ku, Y.Y.; Grieme, T.; Raje, P.; Sharma, P.; Morton, H.E.; Rozema, M.; King, S.A. A practical and scaleable synthesis of A-224817.0, a novel nonsteroidal ligand for the glucocorticoid receptor. J. Org. Chem. 2003, 68, 3238-3240.
22. (a) Ihara, E.; Koyama, K.; Yasuda, H.; Kanehisa, N.; Kai. Y. Catalytic activity of allyl-, azaallyl-and diaza-pentadienyllanthanide complexes for polymerization of methyl methacrylate. J. Organomet. Chem. 1999, 574, 40-49;
23. 2 symmetry. J. Org. Chem. 1989, 54, 980-983;
24. (c) Phillips, J.P.; Elbinger, R.L.; Merrit, L.L. Preparation of some substituted 8-hydroxy-and 8-methoxyquinolines. J. Am. Chem. Soc. 1949, 71, 3986-3988;
25. (d) Volz, H.; Hassler, M. meso-Substituted porphyrins. 5. Basket porphyrins. Z. Naturforsch. 1988, 43b, 1043-1052.
26. Delapierre, G.; Brunel, J.M.; Constantieux, T.; Buono, G. Design of a new class of chiral quinoline-phosphine ligands. Synthesis and application in asymmetric catalysis. Tetrahedron: Asymm. 2001, 12, 1345-1352.
27. (a) Padmavathi, V.; Reddy, B.J.M.; Sarma, M.R.; Padmaja, A.; Reddy, D.B. Cyclohexanone derivatives: synthons for substituted quinolines. Heterocycl. Commun. 2001, 7, 467-472;
28. (b) Padmavathi, V.; Reddy, B.J.M.; Balaiah, A.; Reddy, K.V.; Reddy, D.B. Synthesis of some fused pyrazoles and isoxazoles. Molecules 2000, 5, 1281-1286.
29. Do, C.T.; Kossoff, E.H.; Jacquignon, P.; Dufour, M. Carcinogenic nitrogen compounds. LXXXV. Heterocyclic molecules derived from 3-aminobiphenyl. Coll. Czech. Chem. Commun. 1976, 41, 1212-1218.
30. Gao, X.C.; Cao, H.; Zhang, L.Q.; Zhang, B.W.; Cao Y.; Huang. C.H. Properties of a new pyrazoline derivative and its application in electroluminescence. J. Mater. Chem. 1999, 9, 1077-1080.
31. Sunshine, N.B.; Woods, G.F. Preparation of linear m-polyphenols from mono- and dichalcones. J. Org. Chem. 1963, 28, 2517-2522.
32. Zimmerman, H.E.; Hackett, P.; Juers, D.F.; McCall, J.M.; Schroeder, B. Competitive photochemical pathways in the di-π-methane rearrangement. Exploratory and mechanistic organic photochemistry. LXIII. J. Am. Chem. Soc. 1971, 93, 3653-3662.
33. (a) Clarke, H.T.; Davis, A.W. Quinoline. Org. Synth. 1922, 2, 79-83;
34. (b) Cohn, B. E.; Gustavson, R. G. Modification of the Skraup synthesis of quinoline. J. Am. Chem. Soc. 1928, 50, 2709-2711.
35. Matsugi, M.; Tabusa, F.; Minamikawa, J.-I. Doebner-Miller synthesis in a two-phase system: practical preparation of quinolines. Tetrahedron Lett. 2000, 41, 8523-8525.
36. (a) Bose, D. S.; Kumar, R. K. High-yielding microwave assisted synthesis of quinoline and dihydroquinoline derivatives under solvent-free conditions. Heterocycles 2006, 68, 549-559;
37. (b) Zhang, J.-m., Yang, W.; Song, L.-p.; Cai, X. and Zhu, S.-z. Microwave promoted solvent-free one-pot three-component reaction to 2- pentafluorophenylquinoline derivatives. Tetrahedron Lett. 2004, 45, 5771-5773.
38. Mosettig, E.; Kruger, J.W. Studies in the phenanthrene series. XIX. Naphthoquinolines synthesized from aminophenanthrenes. J. Org. Chem. 1938, 3, 317-339.