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，证明1,3-偶极[3+2]叠氮-腈环加成反应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（alkyl-tetrazole-functionalized compounds）库。由于四唑的碱性较弱，可得到具有弱且易解离的N→B配位作用的目标结构。该反应可得到1-烷基化和2-烷基化区域异构体，二者在硼中心处展现出不同的有效路易斯酸性，且其光吸收与荧光特性存在差异。实验通过11B核磁共振（11B NMR）证实，我们筛选得到了可选择性结合氰根而非氟离子的衍生物。该研究表明，此合成策略可系统微调作为化学传感器的先导结构的相关性能，具备良好应用潜力。 内容： 计算研究输出文件 荧光滴定实验原始数据及分析结果 晶体数据 包含实验步骤与分析数据的PDF格式电子补充信息（ESI，Electronic Supplementary Information）文件