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Molecules 2015, 20(10), 18237-18245; doi:10.3390/molecules201018237

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

1
Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto M5S 3E5, ON, Canada
2
Department of Materials Science and Engineering, University of Toronto, 184 College St., Toronto M5S 3E4, ON, Canada
3
Department of Chemistry, University of Toronto, 80 St. George St., Toronto M5S 3H6, ON, Canada
*
Author to whom correspondence should be addressed.
Academic Editor: Giuseppe Mele
Received: 30 July 2015 / Revised: 16 September 2015 / Accepted: 21 September 2015 / Published: 7 October 2015
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)
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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. View Full-Text
Keywords: boron; subphthalocyanine; alkoxy; alkyl; bromide; endocyclic; carbon; oxygen; bond boron; subphthalocyanine; alkoxy; alkyl; bromide; endocyclic; carbon; oxygen; bond
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Bonnier, C.; Bender, T.P. Ring Opening Reactions through C-O Bond Cleavage Uniquely Adding Chemical Functionality to Boron Subphthalocyanine. Molecules 2015, 20, 18237-18245.

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