Boronic acids have found widespread use in the field of biomaterials, primarily through their ability to bind with biologically relevant 1,2- and 1,3-diols, including saccharides and peptidoglycans, or with polyols to prepare hydrogels with dynamic covalent or responsive behavior. Despite a wide range of boronic acid architectures that have been previously considered, there is a need for greater understanding of the structure-reactivity relationships that govern binding affinity to diols. In this study, various boronic acids and other organoboron compounds were investigated to determine their pKa and their binding constants with the biologically relevant diols including sorbitol, fructose, and glucose. Boronic acid pKa values were determined through spectroscopic titration, whereas binding constants were determined by fluorescence spectroscopy during competitive binding studies. Key structure-reactivity relationships clearly indicated that both boronic acid structure and solution pH must be carefully considered. By considering a variety of boronic acids with systematically varied electronics and sterics, these results provide guidance during selection of organoboron compounds in sensing, delivery, and materials chemistry.

William L. A. Brooks

Christopher C. Deng

Brent S. Sumerlin

ACS Omega

ACS OMEGA 是一个开放获取的全球性科学文章出版物，描述了化学和科学接口领域的新发现，没有对直接影响进行任何感知评估。

ACS Omega is a global open-access scientific journal that focuses on new discoveries in the field of chemistry and its interfaces, without assessing the direct impact of the research.

ACS Omega 是一本开放获取的全球性科学期刊，专注于化学及其相关科学领域的新发现，且不对研究的直接影响进行评估。

Structure–Reactivity Relationships in Boronic Acid–Diol Complexation

Key structure–reactivity relationships clearly indicated that both boronic acid structure and solution pH must be carefully considered during selection of organoboron compounds in sensing, delivery, and materials chemistry.

Category	Quartile
化学	3
化学, 化学综合	3

Structure–Reactivity Relationships in Boronic Acid–Diol Complexation

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Journal Info

Category	Quartile
CHEMISTRY, MULTIDISCIPLINARY	2