Abstract
We report the synthesis and characterization of the missing reference core compound 4,4-Difluoro-4-bora-(3a,4a)-diaza-s-indacene 1 of the BODIPY fluorescent dye class. The compound exhibits a fluorescence lifetime of 7.2 ns and has a high photostability.
References
Treibs A, Kreuzer F-H (1968) Justus Liebigs Ann Chem 718:208–223
Falk H, Hofer O, Lehner H (1974) Monatsh Chem 105:169–178
VosdeWael E, Pardoen JA, Vankoeveringe JA, Lugtenburg J (1977) Recl Trav Chim Pays-Bas 96:306–309
Wories HJ, Koek JH, Lodder G, Lugtenburg J, Fokkens R, Driessen O, Mohn GR (1985) Recl Trav Chim Pays-Bas 104:288–291
Haughland RP, Kang HC (1988) US Patent US4774339
Monsma FJ, Barton AC, Kang HC, Brassard DL, Haughland RP, Sibley DR (1989) J Neurochem 52:1641–1644
Haughland RP (2005) The Handbook, A Guide to Fluorescent Probes and Labeling Technologies, 10th edn, Invitrogen Corp, Eugene. http://probes.invitrogen.com
Boyer JH, Haag AM, Sathyamoorthi G, Soong M-L, Thangaraj K, Pavlopoulos TG (1993) Heteroat Chem 4:39–49
Coskun A, Deniz E, Akkaya EU (2005) Org Lett 7(23):5187–5189
Burghart A, Thoresen LH, Chen J, Burgess K, Bergstrom F, Johansson LBA (2000) Chem Comm 2203–2204
Yogo T, Urano Y, Ishitsuka Y, Maniwa F, Nagano T (2005) J Am Chem Soc 127:12162–12163
Kollmannsberger M, Resch-Genger U, Daub J (2000) J Am Chem Soc 122:968–969
Ulrich G, Ziessel R, Harriman A (2008) Angew Chem Int Ed 47:1184–1201
Loudet A, Burgess K (2007) Chem Rev 107:4891–4932
Burghart A, Kim H, Welch MB, Thorensen LH, Reibenspies J, Burgess K (1999) J Org Chem 64:7813–7819
Kang HC, Haughland RP (1993) US Patent 5187288
Ulrich G, Ziessel R (2004) J Org Chem 69:2070–2083
Morgan LR, Boyer JH (1993) US Patent 5446157
Lakowicz JR (1999) Principles of Fluorescence Spectroscopy, 2nd edn. Kluwer Academic/Plenum Publishers, New York
Horiba Jobin Yvon, A Guide to Recording Fluorescence Quantum Yields, http://www.jobinyvon.com/SiteResources/Data/MediaArchive/files/Fluorescence/applications/quantumyieldstrad.pdf
Lambda Physik, Lambdachrome Laser dyes, http://bcp.phys.strath.ac.uk/ultrafast/Blue_book/Lamdachrome-laser-dyes.pdf
Shah M, Thangaraj K, Soong M-L, Wolford LT, Boyer JH (1990) Heteroatom Chem 1(5):389
Strickler SJ, Berg RA (1962) J Chem Phys 37:814–822
Siebrand W, Williams DF (1967) J Chem Phys 49:403–404
Widengren J, Mets Ü, Rigler R (1995) J Phys Chem 99:13368–13379
Hinkeldey B, Schmitt A, Jung G (2008) ChemPhysChem 9:2019–2027
Acknowledgement
We thank the German Science Foundation (DFG) for financial support (JU650-1) and Benjamin Hötzer for recording fluorescence lifetimes and Volker Huch for performing x-ray crystallography.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Schmitt, A., Hinkeldey, B., Wild, M. et al. Synthesis of the Core Compound of the BODIPY Dye Class: 4,4′-Difluoro-4-bora-(3a,4a)-diaza-s-indacene. J Fluoresc 19, 755–758 (2009). https://doi.org/10.1007/s10895-008-0446-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-008-0446-7