Some observations relating to the stability of the BODIPY fluorophore under acidic and basic conditions

Dyes and Pigments

Volumn 91, Issue 2, 2011, Pages 264-267

  Yang, Lijing ^a   Simionescu, Razvan ^a   Lough, Alan ^b   Yan, Hongbin ^a  

^a BROCK UNIVERSITY   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

11B NMR; Acids and bases; BODIPY; Crystal structure; Fluorophore; Stability

Indexed keywords

11B NMR; AQUEOUS AMMONIUM; BASIC CONDITIONS; BODIPY; TRICHLOROACETIC ACID;

AMMONIUM COMPOUNDS; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

FLUOROPHORES;

EID: 79958780730     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.03.027     Document Type: Article

References (17)

1. A. Treibs, and F.H. Kreuzer Di- and tri-pyrrylmethene complexes with di-fluoro boron Justus Liebigs Ann Chem 718 1968 208 223
2. G. Ulrich, R. Ziessel, and A. Harriman The chemistry of fluorescent bodipy dyes: versatility unsurpassed Angew Chem Int Ed Engl 47 2008 1184 1201
3. A. Loudet, and K. Burgess BODIPY dyes and their derivatives: syntheses and spectroscopic properties Chem Rev 107 2007 4891 4932 (Pubitemid 350225866)
4. R. Ziessel, G. Ulrich, and A. Harriman The chemistry of Bodipy: a new El Dorado for fluorescence tools New J Chem 31 2007 496 501 (Pubitemid 46558017)
5. P. Wang, and R.W. Giese Phosphate-specific fluorescence labeling with BO-IMI: reaction details J Chromatogr A 809 1998 211 218 (Pubitemid 28288269)
6. C. Tahtaoui, C. Thomas, F. Rohmer, P. Klotz, G. Duportail, and Y. Mely Convenient method to access new 4,4-dialkoxy- and 4,4-diaryloxy-diaza-s-indacene dyes: synthesis and spectroscopic evaluation J Org Chem 72 2007 269 272 (Pubitemid 46068228)
7. S.M. Crawford, and A. Thompson Conversion of 4,4-difluoro-4-bora-3a,4a- diaza-s-indacenes (F-BODIPYs) to dipyrrins with a microwave-promoted deprotection strategy Org Lett 12 2010 1424 1427
8. K. Tram, D. Twohig, and H. Yan Oligonucleotide labeling using BODIPY phosphoramidite Nucleos Nucleot Nucleic Acids 30 2011 1 11
9. Z. Otwinowski, and W. Minor Processing of x-ray diffraction data collected in oscillation mode C.W. Carter, R.M. Sweet, Methods in enzymology, macromolecular crystallography, part A vol. 276 1997 Academic press London 307 326 (Pubitemid 27085611)
10. R.H. Blessing An empirical correction for absorption anisotropy Acta Crystallogr A 51 1995 33 38
11. G.M. Sheldrick A short history of SHELX Acta Crystallogr A 64 2008 112 122
12. S. Goeb, and R. Ziessel Synthesis of novel tetrachromophoric cascade-type Bodipy dyes Tetrahedron Lett 49 2008 2569 2574
13. L. Li, B. Nguyen, and K. Burgess Functionalization of the 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) core Bioorg Med Chem Lett 18 2008 3112 3116 (Pubitemid 351680378)
14. Y. Gabe, T. Ueno, Y. Urano, H. Kojima, and T. Nagano Tunable design strategy for fluorescence probes based on 4-substituted BODIPY chromophore: improvement of highly sensitive fluorescence probe for nitric oxide Anal Bioanal Chem 386 2006 621 626 (Pubitemid 44450942)
15. C. Goze, G. Ulrich, L.J. Mallon, B.D. Allen, A. Harriman, and R. Ziessel Synthesis and photophysical properties of borondipyrromethene dyes bearing aryl substituents at the boron center J Am Chem Soc 128 2006 10231 10239 (Pubitemid 44201101)
16. J.J. Led, and H. Gesmar Application of the linear prediction method to NMR-spectroscopy Chem Rev 91 1991 1413 1426
17. A.L. Spek Structure validation in chemical crystallography Acta Crystallogr D Biol Crystallogr 65 2009 148 155