Enhanced Solubility and Deprotection of Pyrene-4,5,9,10-tetraones through Propylene Glycol and Propanediol Protection.

ABSTRACT: Pyrene-4,5,9,10-tetraone (PTO) is a building block of significant interest for functional organic materials. Due to the sensitivity of the vicinal diones toward bases and metal-ion chelation, and low solubility, PTO is typically protected as a ketal with ethylene glycol (EtG). Herein, we report the use of propylene glycol (PrG), propane-1,3-diol (PD) or 2,2-dimethylpropane-1,3-diol (DMPD) for its protection. The PrG-protected PTO has a 44-fold increased solubility relative to EtG-protected PTO due the introduced regio- and stereoisomerism. Protection with PD and DMPD surprisingly produced "half" protected PTOs, with maintained protective capabilities, and milder deprotection conditions for PD. All protected PTOs underwent successful functionalizati

SUBMITTER: Wessling R 

PROVIDER: S-EPMC12584142 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature