Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene DyesBearing New Aryl Substituents at C3- and C5-Positions

  • Lee, Phil-Ho (Department of Chemistry and Institute for Basic Science, Kangwon National University)
  • Published : 2008.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Treibs, A.; Kreuzer, F.-H. Liebigs Ann. Chem. 1968, 718, 208 https://doi.org/10.1002/jlac.19687180119
  2. Johnson, I. D.; Kang, H.-C.; Haugland, R. P. Anal. Biochem. 1991, 198, 228 https://doi.org/10.1016/0003-2697(91)90418-S
  3. Karolin, J.; Johansson, L. B.-A.; Strandberg, L.; Ny, T. J. Am. Chem. Soc. 1994, 116, 7801 https://doi.org/10.1021/ja00096a042
  4. Kurata, S.; Kanagawa, T.; Yamada, K.; Torimura, M.; Yokomaku, T.; Kamagata, Y.; Kurane, R. Nucleic Acids Res. 2001, 29, e34 https://doi.org/10.1093/nar/29.6.e34
  5. Lu, Y.; Prestwich, G. D. Bioconj. Chem. 1999, 10, 755 https://doi.org/10.1021/bc9900338
  6. Li, Z.; Mintzer, E.; Bittman, R. J. Org. Chem. 2006, 71, 1718 https://doi.org/10.1021/jo052029x
  7. Golovkova, T. A.; Kozlov, D. V.; Neckers, D. C. J. Org. Chem. 2005, 70, 5545 https://doi.org/10.1021/jo050540k
  8. Trieflinger, C.; Rurack, K.; Daub, J. Angew. Chem. Int. Ed. 2005, 44, 2288 https://doi.org/10.1002/anie.200462377
  9. Baki, C. N.; Akkaya, E. U. J. Org. Chem. 2001, 66, 1512 https://doi.org/10.1021/jo005706q
  10. Baruah, M.; Qin, W.; Basariæ, N.; De Borggraeve, W. M.; Boens, N. J. Org. Chem. 2005, 70, 4152 https://doi.org/10.1021/jo0503714
  11. Moon, S. Y.; Cha, N. R.; Kim, Y. H.; Chang, S.-K. J. Org. Chem. 2004, 69, 181
  12. Qi, X.; Kim, S. K.; Jun, E. J.; Xu, L.; Kim, S.-J.; Yoon, J. Bull. Korean Chem. Soc. 2007, 28, 2231 https://doi.org/10.5012/bkcs.2007.28.12.2231
  13. Gabe, Y.; Urano, Y.; Kikuchi, K.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 3357 https://doi.org/10.1021/ja037944j
  14. Wagner, R. W.; Lindsey, J. S. Pure & Appl. Chem. 1996, 68, 1373 https://doi.org/10.1351/pac199668071373
  15. Thoresen, L. H.; Kim, H.; Welch, M. B.; Burghart, A.; Burgess, K. Synlett 1998, 1276
  16. Kim, H.; Burghart, A.; Welch, M. B.; Reibenspies, J.; Burgess, K. Chem. Commun. 1999, 1889
  17. Burghart, A.; Kim, H.; Welch, M. B.; Thoresen, L. H.; Reibenspies, J.; Burgess, K. J. Org. Chem. 1999, 64, 7813 https://doi.org/10.1021/jo990796o
  18. Chen, J.; Burghart, A.; Wan, C.-W.; Thai, L.; Ortiz, C.; Reibenspies, J.; Burgess, K. Tetrahedron Lett. 2000, 41, 2303 https://doi.org/10.1016/S0040-4039(00)00166-0
  19. Wan, C.-W.; Burghart, A.; Chen, J.; Bergström, F.; Johansson, L. B.-A.; Wolford, M. F.; Kim, T. G.; Toppe, M. R.; Hochstrasser, R. M.; Burgess, K. Chem. Eur. J. 2003, 9, 4430 https://doi.org/10.1002/chem.200304754
  20. Baruah, M.; Qin, W.; Basariæ, N.; Borggraeve, W. M. D.; Boens, N. J. Org. Chem. 2005, 70, 4125
  21. Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891 https://doi.org/10.1021/cr078381n
  22. Chen, W.; Cava, M. P. Tetrahedron Lett. 1987, 28, 6025 https://doi.org/10.1016/S0040-4039(00)96854-0
  23. Chen, W.; Stephenson, E. K.; Cava, M. P.; Jackson, Y. A. Org. Synth. 1991, 70, 151
  24. Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals, 6th ed.; Molecular Probes Inc.: Eugene, OR, USA, 1996
  25. Rettig, W. Angew. Chem. Int. Ed. 1986, 25, 971 https://doi.org/10.1002/anie.198609711

Cited by

  1. A new, long-wavelength borondipyrromethene sphingosine for studying sphingolipid dynamics in live cells vol.54, pp.1, 2012, https://doi.org/10.1194/jlr.D029207
  2. Blue-to-Orange Color-Tunable Laser Emission from Tailored Boron-Dipyrromethene Dyes vol.14, pp.18, 2013, https://doi.org/10.1002/cphc.201300818
  3. Substituents vol.2013, pp.19, 2013, https://doi.org/10.1002/ejoc.201300212
  4. Direct synthesis of aryl substituted pyrroles from calcium carbide: an underestimated chemical feedstock vol.17, pp.1, 2015, https://doi.org/10.1039/C4GC01615G
  5. ChemInform Abstract: Synthesis of 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene Dyes Bearing New Aryl Substituents at C3- and C5-Positions. vol.39, pp.23, 2008, https://doi.org/10.1002/chin.200823162
  6. Synthesis of BODIPY Chromophores Bearing Fused-Carbocycles vol.31, pp.2, 2010, https://doi.org/10.5012/bkcs.2010.31.02.507
  7. A General Synthetic Strategy for the Design of New BODIPY Fluorophores Based on Pyrroles with Polycondensed Aromatic and Metallocene Substituents vol.17, pp.11, 2008, https://doi.org/10.1002/chem.201003242
  8. Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy vol.2015, pp.30, 2015, https://doi.org/10.1002/ejoc.201500682