Chemoselective Detection of 2,4,6-trinitrophenol by Ground State Adduct Formation via Protonation of Quinoline Moiety of Non-heme Ligands with Structural Evidence

摘要

abstract_textpFour quinoline based non-heme tetradendate ligandsviz. N,N '-di(quinolin-8-yl)ethane-1,2-diamine (BQENH(2))1,N,N '-di(quinolin-8-yl)propane-1,3-diamine2(BQPNH(2)),N,N '-di(quinolin-8-yl)butane-1,4-diamine (BQEBNH(2))3andN,N '-di(quinolin-8-yl)hexane-1,6-diamine (BQEHNH(2))4are structurally characterized and used in selective detection of 2,4,6-trinitrophenol (TNP) with high quenching constants. The plausible reaction mechanism involves ground state protonation of quinoline nitrogen atoms in compounds1-4by TNP with formation of picrate adducts (1 a-4 a). The protonation of1-4is confirmed by infrared,H-1-NMR spectroscopies, powder XRD and the single crystal structure analysis of1 aand4 a. Crystal structures further infer that after protonation,1 aand4 aare stabilized by intramolecular hydrogen bonding./p/abstract_text