Full Conjugation in a Polymer with Non-conjugated Piperazine-2,5-dione Units via Energy-minimized Lactam-to-Lactim Tautomerization Enables Water-gated Transistor Fluoride Sensors.

ABSTRACT: Piperazine-2,5-dione (glycine anhydride, GA) has recently emerged as a valuable precursor for high-performance π-conjugated polymer semiconductors in organic electronics. We utilized GA to design a novel bisindolin-dihydropiperazine (IDHP)-based conjugated polymer, PIDHPTT, for aqueous chemical sensing. In the isatin-flanked monomer, GA exists as a non-conjugated lactam (DHP-NH) but converts to a conjugated lactim (DHP-OH) form within the polymer. Density functional theory (DFT) calculations show that this conversion is driven by energy minimization via extended π-conjugation. Neighboring DHP units in the lactim form facilitate this process through π-bridges, demonstrating a vinylogous effect, which has previously only been observed in small molecules. This is the first study to report suc

SUBMITTER: Zhao N 

PROVIDER: S-EPMC11811691 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature