Boron asymmetry in a BODIPY derivative.
A boradiazaindacene (BODIPY) fluorophore with a chirality held on the central boron has been synthesized and the racemate resolved. Dissymetrization of the BODIPY core was obtained by oxidation of the 3-methyl group to the corresponding carboxaldehyde. A hydrogen bond between the aldehyde proton and the fluorine on the boron atom was evidenced by both (1)H NMR and X-ray diffraction. Chiral high-performance liquid chromatography as well as circular dichroism confirm the persistence of both enantiomers.
Haefele
Alexandre
A
LCOSA, ECPM, UMR 7515, CNRS-UdS, 25 rue Becquerel, 67087 Strasbourg Cedex 02, France.
Zedde
Chantal
C
Retailleau
Pascal
P
Ulrich
Gilles
G
Ziessel
Raymond
R
D000042:Absorption; D001895:Boron / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D001895:Boron