Ring Opening Reactions through C-O Bond Cleavage Uniquely Adding Chemical Functionality to Boron Subphthalocyanine

Catherine Bonnier; Timothy P. Bender

doi:10.3390/molecules201018237

Molecules (Oct 2015)

Ring Opening Reactions through C-O Bond Cleavage Uniquely Adding Chemical Functionality to Boron Subphthalocyanine

Catherine Bonnier,
Timothy P. Bender

Affiliations

Catherine Bonnier: Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto M5S 3E5, ON, Canada
Timothy P. Bender: Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto M5S 3E5, ON, Canada

DOI: https://doi.org/10.3390/molecules201018237
Journal volume & issue: Vol. 20, no. 10
pp. 18237 – 18245

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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