title: Synthesis, spectral, electrochemical, and anion binding properties of 3,5-bis(dipyrromethanyl) boron-dipyrromethenes.
abstract: Four new boron-dipyrromethenes (BODIPYs) containing dipyrromethanyl substituents at 3,5-positions, bis(3,5-dipyrromethanyl) BODIPYs 5-8, were synthesized by treating their corresponding 3,5-diformyl BODIPYs 1-4 with excess pyrrole under mild acid catalyzed reaction conditions. The compounds 5-8 are stable and freely soluble in common organic solvents. One-dimensional, two-dimensional NMR, high resolution mass spectrometry (HRMS), absorption, fluorescence, and electrochemical techniques were used to characterize the compounds. The spectral and electrochemical studies indicated that dipyrromethanyl groups at 3,5-positions of BODIPY are less electron deficient compared to formyl groups at the same positions. The anion binding studies indicated that bis(3,5-dipyrromethanyl) BODIPY compounds containing four pyrrole NH groups showed preferential binding with F(-) ion over other anions, as confirmed by using NMR, fluorescence, and electrochemical studies.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
authors.forename: Sheri
authors.initials: S
authors.lastname: Madhu
authors.forename: Mangalampalli
authors.initials: M
authors.lastname: Ravikanth
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D055664:Electrochemical Techniques; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D005459:Fluorides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D011758:Pyrroles; D005459:Fluorides