Double-Furylogous Methylene Activation for the Production of Bio-Based Dyes
Mark Mascal1, Haoqian Miao1,2, Eva Harsevoort1
1Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, CA, 95616, USA.
Abstract:
Furylogous active methylene compounds retain the ability to undergo Knoevenagel condensations with aromatic aldehydes, leading to highly conjugated molecules with strong chromophores. In this work, a doubly furylogous malonate diester derived from the renewable platform molecule 5-(chloromethyl)furfural is prepared and evaluated for carbon acidity by H-D exchange and computational modeling. Its Knoevenagel adducts with biomass-derived carbonyl compounds (furfurals, phenolic aldehydes) are delocalized, push-pull systems of 3-5 rings that have intense, bright colors from the yellow-to-red region of the spectrum. The dyeing performance and wash fastness of these novel bio-based colorants are found to be excellent.
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