Simple and cost-efficient chlorination of electron deficient aromatics to provide templates for organogelation and fluoride sensing

Abstract

This present work describes the synthesis of extremely electron-deficient novel nitroaromatic compounds from trinitrophenols using new synthetic methods and applying them to derive soft materials. Multi chlorination has been achieved at a single shot using phosphorus oxychloride in both cases. We have explored the mechanism of this new type of transformation using the DFT study. Compounds 2a-b have been successfully utilized to provide a template for organogelation using a non-gelator methyl ester of phenylalanine. Interaction leading towards the gel has also been investigated using the DFT study. Various aspects of this two-component gelation and fluoride mediated gel to sol transformation have been investigated. The fluoride sensing property of compound 2a has also been explored in the THF-water mixture. The yellow solution of compound 2a becomes reddish-brown in presence of fluoride ion. Using compound 2a aqueous fluoride can be detected down to 12.2 ppb level.