Pyrrolidylsubstituted azadipyrromethene with fully chelated boron atom

Synthetic Communications

Volumn 40, Issue 7, 2010, Pages 944-950

  Yakubovskyi, Viktor P ^a   Shandura, Mykola P ^a   Kovtun, Yuriy P ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

BODIPY; Boradiaza s indacene; Long wavelength dye

Indexed keywords

AMMONIUM ACETATE; BORON; BORON TRIFLUORIDE; DIFLUOROSUBSTITUTED AZA BORON DIPYRROMETHENE DERIVATIVE; FLUORINE; KETONE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHELATION; FLUORESCENCE SPECTROSCOPY; LIGHT ABSORPTION; QUANTUM YIELD; SYNTHESIS;

EID: 77749248973     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903219542     Document Type: Article

References (24)

1. For recent reviews, see: (a) Loudet, A; Burgess, K. BODIPY dyes and their derivatives: Syntheses and spectroscopic properties. Chem. Rev. 2007, 107, 4891-4932;
2. (b) Ulrich, G; Ziessel, R; Harriman, A. The chemistry of fluorescent BODIPY dyes: Versatility unsurpassed. Angew. Chem. Int. Ed. 2008, 47, 1184-1201;.
3. (c) Wood, T. E; Thompson, A. Advances in the chemistry of dipyrrins and their complexes. Chem. Rev. 2007, 107, 1831-1861;.
4. (d) Haugland, R. P. The Handbook: A Guide to Fluorescence Probes and Labeling Technologies, 10th ed; Invitrogen Corp.: Eugene, OR, 2005.
5. (a) Rurack, K; Kollmannsberger, M; Daub, J. A highly efficient sensor molecule emitting in the near infrared (NIR): 3,5-Distyryl-8-(p- dimethylaminophenyl)-difluoroboradiaza-s-indacene. New J. Chem. 2001, 25, 289-292;.
6. (b) Coskun, A; Akkaya, E. U. Difluoro-bora-s-diazaindacene dyes as highly selective dosimetric reagents for fluoride anions. Tetrahedron Lett. 2004, 45, 4947-4949;.
7. (c) Rohald, T; Qin, W; Boens, N; Dehaen, W. Palladium-catalyzed coupling reactions for the functionalization of BODIPY dyes with fluorescence spanning the visible spectrum. Eur. J. Org. Chem. 2006, 4658-4663;.
8. (d) Rurack, K; Kollmannsberger, M; Daub, J. Molecular switching in the near infrared (NIR) with a functionalized boron-dipyrromethene dye. Angew. Chem. Int. Ed. 2001, 40, 385-387;. (Pubitemid 32117657)
9. (e) Yu, Y.-H; Descalzo, A. B; Shen, Z; Rohr, H; Li, Q; Wang, Y.-W; Spieles, M; Li, Y.-Z; Rurack, K; You, X.-Z. Mono-and di(dimethylamino)styryl- substituted borondipyrromethene and borondiindomethene dyes with intense near-infrared fluorescence. Chem.-Asian J. 2006, 1-2, 176-187;.
10. (f) Saki, N; Dinc, T; Akkaya, E. U. Excimer emission and energy transfer in cofacial boradiazaindacene (BODIPY) dimers built on a xanthene scaffold. Tetrahedron 2006, 62, 2721-2725;.
11. 2\+ in living cells. J. Am. Chem. Soc. 2007, 129, 1500-1501
12. (a) For reviews, see Matsuoka, M. Infrared Absorbing Dyes; Plenum: New York, 1990;.
13. (b) Fabian, J; Nakazumi, H; Matsuoka, M. Near-infrared absorbing dyes. Chem. Rev. 1992, 92, 1197-1226;
14. (c) Dahne, S; Resch-Genger, U; Wolfbeis, O. S. (Eds.). Near-Infrared Dyes for High Technology Application; Kluwer Academic: Dordrecht 1998.
15. 2 chelates of tetraarylazadipyrromethenes and evidence for their photodynamic therapeutic behaviour. Chem. Commun. 2002, 1862-1863;.
16. (b) Hall, M. J; McDonnel, S. O; Killoran, J; O'Shea, D. F. A modular synthesis of unsymmetrical tetraarylazadipyrro-methenes. J. Org. Chem. 2005, 70, 5571.
17. 2-azadipyrromethenes. Org. Lett. 2006, 8, 3493-3496.
18. Kim, H; Burghart, A; Welch, M. B; Reibenspies, J; Burgess, K. Synthesis and spectro-scopic properties of a new 4-bora-3a,4a-diaza-s-indacene (BODIPY) dye. Chem. Commun. 1999, 1889-1890.
19. Yakubovskyi, V. P; Shandura, M. P; Kovtun Yu, P. Azadipyrromethene dye with a fully chelated boron anom. Chem. Het. Comp. 2008, 44, 1298.
20. Loudet, A; Bandichhor, R; Burgess, K; Palma, A; McDonnell, S. O; Hall, M. J; O'Shea, D. F. B,O-Chelated azadipyrromethenes as near-IR probes. Org. Lett. 2008, 10, 4771-4774.
21. Gorman, A; Killoran, J; O'Shea, C; Kenna, T; Gallagher, W. M; O'Shea, D. F. In vitro demonstration of the heavy-atom effect for photodynamic therapy. J. Am. Chem. Soc. 2004, 126, 10619-10631.
22. Poronik, E. M; Shandura, M. P; Kovtun, Y. P. Method for preparative synthesis of 4-dialkylamino-2-hydroxyacetophenone. Chem. Het. Comp. 2005, 41, 546-547.
23. Spitzer, W. A; Frantz, V; Don Pollock, G; Hayes, J. S. Imidazo[1,2-a]pyrimidines and imidazo[1,2-a]pyrazines: The role of nitrogen position in inotropic activity. J. Med. Chem. 1988, 31, 1590-1595.
24. Gerasov, A; Shandura, M; Kovtun, Y. Series of polymethine dyes derived from 2,2-difluoro-1,3,2-(2H)-dioxaborine of 3-acetyl-7-diethylamino-4- hydroxycoumarin. Dyes Pigm. 2008, 77, 598-607