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 filed from Computational Studies Raw data and Analysis from Fluorescence Titrations Crystal data ESI file in .pdf format containing experimental procedures and analytical data.摘要：本研究以两种不同的氰基官能化有机硼烷（cyano-functionalized organoboranes）为起始原料，证实1,3-偶极[3+2]叠氮-腈环加成反应（1,3-dipolar [3+2] azide-nitrile cycloaddition）可用于构建可形成分子内N→B路易斯加合物的烷基四唑官能化化合物库。鉴于四唑的碱性较弱，可得到具有弱且不稳定N→B配位作用的分子结构。该反应可生成1-位与2-位烷基化的区域异构体（regio-isomers），二者在硼中心展现出不同的有效路易斯酸性，且光吸收与荧光特性存在差异。实验通过硼-11核磁共振波谱（11B NMR）证实，部分衍生物可选择性结合氰离子而非氟离子。该发现表明，此合成策略具备系统性微调作为化学传感器候选先导结构的性能的潜力。 内容： 计算研究输出文件 荧光滴定实验原始数据与分析结果 晶体学数据 包含实验步骤与分析数据的PDF格式电喷雾电离（Electrospray Ionization, ESI）文件