Near-infrared BODIPY dyes modulated with spirofluorene moieties

Tetrahedron

Volumn 67, Issue 17, 2011, Pages 3105-3110

  Kowada, Toshiyuki ^a   Yamaguchi, Shuhei ^a   Fujinaga, Hiroki ^a   Ohe, Kouichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

BODIPY dye; C H arylation; Charge transfer; Fluorescence; Near infrared

Indexed keywords

BENZENE; CARBON; CYCLOHEXANE; DYE; FLUORENE DERIVATIVE; HYDROGEN; PALLADIUM; PYRROLE; TRIFLUOROACETIC ACID;

ADDITION REACTION; ADSORPTION; ARTICLE; ARYLATION; CATALYSIS; ELECTRON TRANSPORT; FLUORESCENCE; NEAR INFRARED REFLECTANCE SPECTROSCOPY; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 79953710528     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.02.073     Document Type: Article

References (48)

1. A. Loudet, and K. Burgess Chem. Rev. 107 2007 4891 4932
2. G. Ulrich, R. Ziessel, and A. Harriman Angew. Chem., Int. Ed. 47 2008 1184 1201
3. L.D. Lavis, and R.T. Raines ACS Chem. Biol. 3 2008 142 155
4. A. Wakamiya, N. Sugita, and S. Yamaguchi Chem. Lett. 37 2008 1094 1095
5. T. Rohand, W. Qin, N. Boens, and W. Dehaen Eur. J. Org. Chem. 2006 4658 4663
6. W. Qin, T. Rohand, W. Dehaen, J.N. Clifford, K. Driesen, D. Beljonne, B. Van Averbeke, M. Van der Auweraer, and N. Boens J. Phys. Chem. A 111 2007 8588 8597
7. Z. Dost, S. Atilgan, and E.U. Akkaya Tetrahedron 62 2006 8484 8488
8. J. Chen, A. Burghart, A. Derecskei-Kovacs, and K. Burgess J. Org. Chem. 65 2000 2900 2906
9. K. Umezawa, Y. Nakamura, H. Makino, D. Citterio, and K. Suzuki J. Am. Chem. Soc. 130 2008 1550 1551
10. L. Wu, and K. Burgess Chem. Commun. 2008 4933 4935
11. Y. Mei, P.A. Bentley, and W. Wang Tetrahedron Lett. 47 2006 2447 2449
12. For aza-BODIPY derivatives, see: W. Zhao, and E.M. Carreira Angew. Chem., Int. Ed. 44 2005 1677 1679
13. W. Zhao, and E.M. Carreira Chem. - Eur. J. 12 2006 7254 7263
14. 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
15. A. Burghart, H. Kim, M. Weich, L.H. Thoresen, J. Reibenspies, K. Burgess, F. Bergström, and L.B.-. Johansson J. Org. Chem. 64 1999 7813 7819
16. J.-Y. Liu, H.-S. Yeung, W. Xu, X. Li, and D.K.P. Ng Org. Lett. 10 2008 5421 5424
17. R. Ziessel, G. Ulrich, A. Harriman, M.A.H. Alamiry, B. Stewart, and P. Retailleau Chem. - Eur. J. 15 2009 1359 1369
18. K. Yamada, T. Toyota, K. Takakura, M. Ishimaru, and T. Sugawara New J. Chem. 25 2001 667 669
19. O. Buyukcakir, O.A. Bozdemir, S. Kolemen, S. Erbas, and E.U. Akkaya Org. Lett. 11 2009 4644 4647
20. K. Rurack, M. Kollmannsberger, and J. Daub Angew. Chem., Int. Ed. 40 2001 385 387
21. A. Coskun, E. Denis, and E.U. Akkaya Org. Lett. 7 2005 5187 5189
22. L. Bonardi, G. Ulrich, and R. Ziessel Org. Lett. 10 2008 2183 2186
23. E. Deniz, G.C. Isbasar, ÖA. Bozdemir, L.T. Yildirim, A. Siemiarczuk, and E.U. Akkaya Org. Lett. 10 2008 3401 3403
24. M. Baruah, W. Qin, C. Flors, J. Hofkens, R.A.L. Vallée, D. Beljonne, M. Van der Auweraer, W.M. De Borggraeve, and N. Boens J. Phys. Chem. A 110 2006 5998 6009
25. N. Saki, T. Dinc, and E.U. Akkaya Tetrahedron 62 2006 2721 2725
26. Y.-H. Yu, A.B. Descalzo, Z. Shen, H. Röhr, Q. Liu, Y.-W. Wang, M. Spieles, Y.-Z. Li, K. Rurack, and X.-Z. You Chem. - Asian J. 1-2 2006 176 187
27. X. Peng, J. Du, J. Fan, J. Wang, Y. Wu, J. Zhao, S. Sun, and T. Xu J. Am. Chem. Soc. 129 2007 1500 1501
28. S. Atilgan, T. Ozdemir, and E.U. Akkaya Org. Lett. 10 2008 4065 4067
29. M. Yuan, Y. Li, J. Li, C. Li, X. Liu, J. Lv, J. Xu, H. Liu, S. Wang, and D. Zhu Org. Lett. 9 2007 2313 2316
30. M. Baruah, W. Qin, R.A.L. Vallée, D. Beljonne, T. Rohand, W. Dehaen, and N. Boens Org. Lett. 5 2005 4377 4380
31. W. Qin, M. Baruah, M. Sliwa, M. Van der Auweraer, W.M. De Borggraeve, D. Beljonne, B. Van Averbeke, and N. Boens J. Phys. Chem. A 112 2008 6104 6114
32. A. Coskun, and E.U. Akkaya J. Am. Chem. Soc. 127 2005 10464 10465
33. R. Guliyev, A. Coskun, and E.U. Akkaya J. Am. Chem. Soc. 131 2009 9007 9013
34. A. Coskun, and E.U. Akkaya J. Am. Chem. Soc. 128 2006 14474 14475
35. X. Qi, S.K. Kim, S.J. Han, L. Xu, A.Y. Jee, H.N. Kim, C. Lee, Y. Kim, M. Lee, S.-J. Kim, and J. Yoon Tetrahedron Lett. 49 2008 261 264
36. X. Qi, E.J. Jun, L. Xu, S.-J. Kim, J.S.J. Hong, Y.J. Yoon, and J. Yoon J. Org. Chem. 71 2006 2881 2884
37. T. Kowada, S. Yamaguchi, and K. Ohe Org. Lett. 12 2010 296 299
38. H. Sunahara, Y. Urano, H. Kojima, and T. Nagano J. Am. Chem. Soc. 129 2007 5597 5604
39. Y. Gabe, Y. Urano, K. Kikuchi, H. Kojima, and T. Nagano J. Am. Chem. Soc. 126 2004 3357 3367
40. D.P. Kennedy, C.M. Kormos, and S.C. Burdette J. Am. Chem. Soc. 131 2009 8578 8586
41. M. Baruah, W. Qin, N. Basarić, W.M. De Borggraeve, and N. Boens J. Org. Chem. 70 2005 4152 4157
42. For recent reviews, see: (a) D. Alberico, M.K. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
43. (b) T. Satoh, and M. Miura Chem. Lett. 36 2007 200 205
44. (c) L.-C. Campeau, D.R. Stuart, and K. Fagnou Aldrichimica Acta 40 2007 35 41
45. In our previous paper (Ref. 10), we used sodium hydroxide for a detosylation of sp-FIP precursor and obtained sp-FIP in 99% yield. However, in the case of 4a and 4b, the reaction systems were so complicated that the yields were 40% and 0%, respectively.
46. B. Valeur Molecular Fluorescence 2002 Wiley-VCH Weinheim, Germany
47. M. Sugiura, and K. Hirano Biochem. Med. 17 1977 222 228
48. T. Jensen, H. Pedersen, B. Bang-Andersen, R. Madsen, and M. Jørgensen Angew. Chem., Int. Ed. 47 2008 888 890