title: Hydrogen-bond rigidified BODIPY dyes.
abstract: Boron difluoride adducts of diamidodipyrromethenes have been synthesized and characterized. The compounds represent a new group of the BODIPY family of fluorescent dyes. X-ray crystallography and solution (19)F NMR experiments show that a persistent hydrogen bond is formed between the boron-bound fluoride groups and the peripheral amide substituents. The modular synthesis of these compounds and their robust photophysical properties suggest that they may be useful compounds for materials and biological photochemical applications.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0358, USA.
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Jacobsen
authors.forename: Jay R
authors.initials: JR
authors.lastname: Stork
authors.forename: Douglas
authors.initials: D
authors.lastname: Magde
authors.forename: Seth M
authors.initials: SM
authors.lastname: Cohen
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000737:chemistry*; D006860:Hydrogen Bonding; D012995:Solubility; D013057:Spectrum Analysis
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes