Synthesis of thiophene-substituted aza-BODIPYs and their optical and electrochemical properties

Tetrahedron

Volumn 67, Issue 37, 2011, Pages 7148-7155

  Gresser, Roland ^a   Hartmann, Horst ^a   Wrackmeyer, Marion ^a   Leo, Karl ^a   Riede, Moritz ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Aza BODIPY; Cyclic voltammetry; DFT calculations; NIR absorption; Stille coupling

Indexed keywords

2 TRIBUTYLSTANNYL THIOPHENE; 4 NITRO 1,3 DI(HET)ARYLBUTANONE DERIVATIVE; ALKANONE; AMMONIUM ACETATE; AZA BORON DIFLUORIDE DIPYRROMETHENE DERIVATIVE; BORON DERIVATIVE; FLUORESCENT DYE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; BROMINATION; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; SPECTROSCOPY; STILLE REACTION; SUBSTITUTION REACTION;

EID: 80051687795     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.06.100     Document Type: Article

References (59)

1. R. Ziessel, G. Ullrich, and A. Harriman New J. Chem. 31 2007 496 501
2. A. Loudet, and K. Burgess Chem. Rev. 107 2007 4891 4932
3. T.E. Wood, and A. Thompson Chem. Rev. 107 2007 1831 1861
4. Y. Urano, D. Asanuma, Y. Hama, Y. Koyama, T. Barrett, M. Kamiya, T. Nagano, T. Watanabe, A. Hasegawa, P.L. Choyke, and H. Kobayashi Nat. Med. 15 2009 104 109
5. J.-S. Lee, N.-Y. Kang, Y.K. Kim, A. Samanta, S. Feng, H.K. Kim, M. Vendrell, J.H. Park, and Y.-T. Chang J. Am. Chem. Soc. 131 2009 10077 10082
6. A. Hepp, G. Ulrich, R. Schmechel, H. von Seggern, and R. Ziessel Synth. Met. 146 2004 11 15
7. T. Rousseau, A. Cravino, T. Bura, G. Ulrich, R. Ziessel, and J. Roncali Chem. Commun. 2009 1673 1675
8. T. Rousseau, A. Cravino, T. Bura, G. Ullrich, R. Ziessel, and J. Roncali J. Mater. Chem. 19 2009 2298 2300
9. M.A.T. Rogers J. Chem. Soc. 1943 590 596
10. W.H. Davies, and M.A.T. Rogers J. Chem. Soc. 1944 126 131
11. E.B. Knott J. Chem. Soc. 1947 1196 1201
12. M.J. Hall, S.O. McDonnell, J. Killoran, and D.F. O'Shea J. Org. Chem. 70 2005 5571 5578
13. J. Killoran, L. Allen, J. Gallagher, W.M. Gallagher, and D.F. O'Shea Chem. Commun. 2002 1862 1863
14. S.O. McDonnell, M.J. Hall, L.T. Allen, A. Byrne, W.M. Gallaher, and D.F. O'Shea J. Am. Chem. Soc. 127 2005 16360 16361
15. A.D. Quartarolo, N. Russo, and E. Sicilia Chem. - Eur. J. 12 2006 6797 6803
16. N. Adarsh, R.R. Avirah, and D. Ramaiah Org. Lett. 12 2010 5720 5723
17. W. Zhao, and E.M. Carriera Angew. Chem., Int. Ed. 44 2005 1677 1678
18. A. Loudet, R. Bandichhor, L. Wu, and K. Burgess Tetrahedron 64 2008 3642 3654
19. A. Loudet, R. Bandichhor, K. Burgess, A. Palma, S.O. McDonnell, M.J. Hall, and D.F. O'Shea Org. Lett. 10 2008 4771 4774
20. Y. Li, D. Dolphin, and B.O. Patrick Tetrahedron Lett. 51 2010 811 814
21. A. Coskun, D. Yilmaz, and E.U. Akkaya Org. Lett. 9 2007 607 609
22. A. Palma, M. Tasor, D.O. Frimannsson, T.T. Vu, R. Méallet-Renault, and D.F. O'Shea Org. Lett. 11 2009 3638 3641
23. R. Yoshii, A. Nagai, and Y. Chujo J. Polym. Sci., Part A: Polym. Chem. 48 2010 5348 5356
24. E.Y. Schmidt, B.A. Trovimov, A.I. Mikhaleva, N.V. Zorina, N.I. Protzuk, K.B. Petrushenko, I.A. Ushakov, M.Y. Dvorko, R. Méallet-Renault, G. Clavier, T.T. Vu, H.T.T. Tran, and R.B. Pans Chem. - Eur. J. 15 2009 5823 5830
25. S. Zrig, P. Rémy, B. Andrioletti, E. Rose, I. Asselberghs, and K. Clays J. Org. Chem. 73 2008 1563 1566
26. D. Collado, J. Casado, S. Rodríguez González, J.T. López Navarrete, R. Suau, E. Perez-Inestrosa, T.M. Pappenfus, and M.M.M. Raposo Chem. - Eur. J. 17 2011 498 507
27. S. Rihn, P. Retailleau, N. Bugsaliewicz, A. DeNicola, and R. Ziessel Tetrahedron Lett. 50 2009 7008 7013
28. R. Gresser, M. Hummert, H. Hartmann, K. Leo, and M. Riede Chem. - Eur. J. 17 2011 2939 2947
29. G. Ulrich, S. Goeb, A. De Nicola, P. Retailleau, and R. Ziessel Synlett 2007 1517 1520
30. A.C. Benniston, G. Copley, A. Harriman, D.B. Rewinska, R.W. Harrington, and W. Clegg J. Am. Chem. Soc. 130 2008 7174 7175
31. S. Goeb, and R. Ziessel Tetrahedron Lett. 49 2008 2569 2574
32. J.C. Forgie, P.J. Skabara, I. Stibor, F. Vilela, and Z. Vobecka Chem. Mater. 21 2009 1784 1786
33. S.H. Choi, K. Pang, K. Kim, and D.G. Churchill Inorg. Chem. 46 2007 10564 10577
34. S.H. Choi, K. Kim, J. Jeo, B. Meka, D. Bucella, K. Pang, S. Khatu, J. Lee, and D.G. Churchill Inorg. Chem. 47 2008 11071 11083
35. K. Kim, C. Jo, S. Easwaramoorti, J. Sung, D.H. Kim, and D.G. Churchill Inorg. Chem. 49 2010 4881 4894
36. S. Goeb, and R. Ziessel Org. Lett. 9 2007 737 740
37. K. Schwetlick Organikum 23 ed. 2009 Wiley-VCH Weinheim
38. A. Gorman, J. Killoran, C. O'Shea, T. Kenna, W.M. Gallagher, and D.F. O'Shea J. Am. Chem. Soc. 126 2004 10619 10631
39. A. Treibs, and F.H. Kreuzer Liebigs Ann. Chem. 718 1968 208 223
40. M. Klessinger, and J. Michl Excited States and Photochemistry of Organic Molecules 1995 J. Wiley New York, NY
41. J. Heinze Angew. Chem. 96 1984 823 840
42. J. Roncali Chem. Rev. 92 1992 711 738
43. RED
44. A detailed comparison of 1d, 2 and 8, including the absorption spectra and the cyclic voltammograms is shown in the Supplementary data.
45. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven Jr., 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, V. Bakken, 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, and J.A. Pople Gaussian 03, Revision E.01 2004 Gaussian, Wallingford CT
46. J. Fabian, and H. Hartmann Light Absorption of Organic Colorants 1980 Springer Berlin, Heidelberg
47. W. Zhao, and E.M. Carreira Chem. - Eur. J. 12 2006 7254 7263
48. See the Supporting Data for cartesian coordinates of the optimized molecular geometries of the aza-BODIPYs 1a-d.
49. A. Szabo, and N.S. Ostlund Modern Quantum Chemistry 1996 Doverl Mineola, New York, NY
50. C.J. Cramer Essentials of Computational Chemistry: Theories and Models 2nd ed. 2004 Wiley-VCH Weinheim
51. The TD-DFT approach has proven to be superior compared to semi-empirical methods; see J. Fabian Dyes Pigm. 84 2010 36 53
52. A.T.R. Williams, S.A. Winfield, and J.N. Miller Analyst 108 1983 1067 1071
53. T. Karstens, and K. Kobs J. Phys. Chem. 84 1980 1871 1872
54. K. Rurack, and M. Spieles Anal. Chem. 83 2001 1232 1242
55. J.R. Lakowicz Principles of Fluorescence Spectroscopy 2nd ed. 1999 Kluwer Academic/Plenum New York, NY, London, Moscow, Dordrecht
56. H.-H. Koa, L.-T. Tsaob, K.-L. Yuc, C.-T. Liuc, J.-P. Wangb, and C.-N. Lin Bioorg. Med. Chem. 11 2003 105 111
57. B. Ramesh, and B. Someswara Rao E-J. Chem. 7 2010 433 436
58. G. Dannhardta, W. Kiefera, G. Krämera, S. Maehrleina, U. Nowea, and B. Fiebich Eur. J. Med. Chem. 35 2000 499 510
59. K. Peseke, L. Götze, H. Reinke, Q.A. Cedeño, J. Quincoces Suarez, M. Gomez Andreu, and H. Vélez Castro J. Prakt. Chem. 339 1997 656 659