Amino-Terephthalonitrile Based Single Benzene Fluorophores Bearing Amino Esters and Lipids for Selective Biothiol Sensing and Bioimaging

Abstract

We report here the preparation of eight new AmTN SBFs which feature amino esters with an N-terminal fluorophore and also lipophilic dyes, consisting of a push-pull AmTN moiety. Spectrofluorimetric and NMR titration investigations reveal the preference of the terephthalonitirle ring in mono AmTNs towards rapid sensing of N-acetyl cysteine, as opposed to the dipeptide carnosine. This has significance in the field of bioanalysis whereby the AmTNs could show their potential as thiol sensing platforms. Also, one of the lipophilic green emissive AmTNs featuring two cyclohexyl units proved its worth in fluorescence imaging using C2 C12 cells, where it localized electively inside the cell cytoplasm at concentration of 1 μM. © 2025 Wiley-VCH GmbH.