title: Ring Opening Reactions through C-O Bond Cleavage Uniquely Adding Chemical Functionality to Boron Subphthalocyanine.
abstract: We are reporting the unexpected reaction between bromo-boron subphthalocyanine (Br-BsubPc) and THF, 1,4-dioxane or γ-butyrolactone that results in the ring opening of the solvent and its addition into the BsubPc moiety. Under heating, the endocyclic C-O bond of the solvent is cleaved and the corresponding bromoalkoxy-BsubPc derivative is obtained. These novel alkoxy-BsubPc derivatives have remaining alkyl-bromides suitable for further functionalization. The alkoxy-BsubPcs maintain the characteristic strongly absorption in visible spectrum and their fluorescence quantum yields.
authors.affiliation: Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto M5S 3E5, ON, Canada.
authors.forename: Catherine
authors.initials: C
authors.lastname: Bonnier
authors.affiliation: Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto M5S 3E5, ON, Canada. tim.bender@utoronto.ca.|Department of Materials Science and Engineering, University of Toronto, 184 College St., Toronto M5S 3E4, ON, Canada. tim.bender@utoronto.ca.|Department of Chemistry, University of Toronto, 80 St. George St., Toronto M5S 3H6, ON, Canada. tim.bender@utoronto.ca.
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Bender
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004146:Dioxanes / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D054833:Isoindoles; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D001896:Boron Compounds; D004146:Dioxanes; D007211:Indoles; D054833:Isoindoles; D007783:Lactones; C025223:1,4-dioxane; C013647:phthalocyanine
keywords: alkoxy; alkyl; bond; boron; bromide; carbon; endocyclic; oxygen; subphthalocyanine