Supporting Information for "Tetrazole-functionalized Organoboranes Exhibiting Dynamic Intramolecular N→B-Coordination and Cyanide-selective Anion Bin"

Abstract: Starting from two different cyano-functionalized organoboranes, we demonstrate that 1,3-dipolar [3+2] azide-nitrile cy-cloaddition can serve to generate libraries of alkyl-tetrazole-functionalized compounds capable of intramolecular NB-Lewis adduct formation. Due to the lower basicity of tetrazoles, structures can be generated that exhibit weak and labile NB-coordination. The reaction furnishes 1- and 2-alkylated regio-isomers that exhibit different effective Lewis-acidities at the boron centers, and vary in their optical absorption and fluorescence properties. Indeed, we identified derivatives capable of selectively binding cyanide over fluoride, as confirmed by 11B NMR. This finding demonstrates the potentialities of this synthetic strategy to systematically finetune the properties of lead structures that are of interest as chemical sensors.

Content:

• Output files from Computational Studies
• Raw data and Analysis from Fluorescence Titrations
• Crystal data
• ESI file in .pdf format containing experimental procedures and analytical data.