Macrocyclic geminal diols: synthesis, structures, stability and photophysical properties.

ABSTRACT: Geminal diols are generally unstable and prone to dehydration, yielding carbonyl compounds and making their isolation as discrete species highly challenging. Herein, we report the synthesis, structural characterization, and stability of a series of crystalline, stable, and rigid macrocyclic gem-diols obtained via acid hydrolysis of macrocyclic ketal precursors at -25 °C. Single-crystal X-ray diffraction analysis of these compounds reveals O-C-O bond angles of approximately 111°, along with extensive hydrogen-bonding networks that contribute to stabilizing the gem-diols. Thermogravimetric and hydrolytic analyses reveal a pronounced size-dependent stability trend. Theoretical calculations indicate that the enhanced stability of smaller gem-diol macrocycles stems f

SUBMITTER: Zou B 

PROVIDER: S-EPMC12628340 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature