Boronate Esters for the Binding and Detection of Low Molecular Weight Volatile Amines

Author(s)

• Xiaoning Li
• James Boyt
• Steven Sloope
• Luke T. Lackovic
• Mark D. Smith
• James J. Lavingne, University of South CarolinaFollow

Document Type

Article

Abstract

Conjugated thiophene-based diboronate esters, 1–4, were synthesized to investigate how substituents on catechol alter the Lewis acidity and accessibility to boron, and influence binding interactions with low molecular weight Lewis basic amines. Crystallographic analysis indicated that both boron centres bind analyte and that Lewis base coordination induces deplanarization of the conjugated system. Spectroscopic studies demonstrate that amine binding disrupts conjugation, producing distinct and reproducible optical responses that depend on analyte basicity and structure, with association constants in organic solvent ranging from 10³ to 10⁶ M⁻¹. Quantitative binding analyses indicate strong negative cooperativity between the two boron sites. These results establish design principles for cross-reactive optical sensor arrays capable of differentiating volatile amines relevant to environmental monitoring, food quality assessment, and biomedical diagnostics.

Digital Object Identifier (DOI)

https://doi.org/10.1039/D5DT02760H

Publication Info

Published in Dalton Transactions, Volume 55, 2026, pages 3120-3126.

Rights

© The Royal Society of Chemistry 2026 This article is licensed under a >Creative Commons Attribution 3.0 Unported Licence.

APA Citation

Li, X., Boyt, J., Cai, M., Sloope, S., Lackovic, L. T., Smith, M. D., & Lavigne, J. J. (2026). Boronate esters for the binding and detection of low molecular weight volatile amines. Dalton Transactions, 55(7), 3120–3126.https://doi.org/10.1039/D5DT02760H