Synthesis of the Core Compound of the BODIPY Dye Class: 4,4′-Difluoro-4-bora-(3a,4a)-diaza-s-indacene

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.

[1]  R. Haugland The Handbook: A Guide to Fluorescent Probes and Labeling Technologies , 2005 .

[2]  J. Lakowicz Principles of fluorescence spectroscopy , 1983 .

[3]  Kevin Burgess,et al.  BODIPY dyes and their derivatives: syntheses and spectroscopic properties. , 2007, Chemical reviews.

[4]  R. Rigler,et al.  Fluorescence correlation spectroscopy of triplet states in solution: a theoretical and experimental study , 1995 .

[5]  K. Burgess,et al.  Energy transfer cassettes based on BODIPY® dyes , 2000 .

[6]  J. Lugtenburg,et al.  Pyrromethene-BF2 complexes (4,4′-difluoro-4-bora-3a,4a-diaza-s-indacenes). Synthesis and luminescence properties , 1977 .

[7]  S. J. Strickler,et al.  Relationship between Absorption Intensity and Fluorescence Lifetime of Molecules , 1962 .

[8]  K. Burgess,et al.  3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes: Synthesis, Spectroscopic, Electrochemical, and Structural Properties , 1999 .

[9]  J. H. Boyer,et al.  Pyrromethene-BF2 Complexes and Laser Dyes: 2 , 1990 .

[10]  G. Jung,et al.  Comparative photostability studies of BODIPY and fluorescein dyes by using fluorescence correlation spectroscopy. , 2008, Chemphyschem : a European journal of chemical physics and physical chemistry.

[11]  A. Coskun,et al.  Effective PET and ICT switching of boradiazaindacene emission: a unimolecular, emission-mode, molecular half-subtractor with reconfigurable logic gates. , 2005, Organic letters.

[12]  T. Pavlopoulos,et al.  Pyrromethene–BF2 complexes as laser dyes: 2 , 1993 .

[13]  Digby F. Williams,et al.  Isotope Rule for Radiationless Transitions with an Application to Triplet Decay in Aromatic Hydrocarbons , 1967 .

[14]  G. Ulrich,et al.  Convenient and efficient synthesis of functionalized oligopyridine ligands bearing accessory pyrromethene-BF2 fluorophores. , 2004, The Journal of organic chemistry.

[15]  D. Sibley,et al.  Characterization of Novel Fluorescent Ligands with High Affinity for D1 and D2 Dopaminergic Receptors , 1989, Journal of neurochemistry.

[16]  H. Lehner,et al.  Beiträge zur Chemie der Pyrrolpigmente, 1. Mitt.: Der induzierte Circulardichroismus einiger Pyrromethenderivate in cholesterischer Mesophase , 1974 .

[17]  S. Hoff,et al.  Preparation, metallation and alkylation of allenyl ethers , 2010 .

[18]  K. Rurack,et al.  A Selective and Sensitive Fluoroionophore for HgII, AgI, and CuII with Virtually Decoupled Fluorophore and Receptor Units , 2000 .

[19]  Y. Urano,et al.  Highly efficient and photostable photosensitizer based on BODIPY chromophore. , 2005, Journal of the American Chemical Society.

[20]  R. Fokkens,et al.  A novel water-soluble fluorescent probe: Synthesis, luminescence and biological properties of the sodium salt of the 4-sulfonato-3,3′,5,5′-tetramethyl-2,2′-pyrromethen-1,1′-BF2 complex† , 1985 .

[21]  Anthony Harriman,et al.  The chemistry of fluorescent bodipy dyes: versatility unsurpassed. , 2008, Angewandte Chemie.

[22]  F. Kreuzer,et al.  Difluorboryl‐Komplexe von Di‐ und Tripyrrylmethenen , 1968 .