title: Colorimetric anion sensing and color imaging based on catalyzed deprotection in a new azonaphthol chromophore.
abstract: We synthesized an ortho-phenylazonaphthol compound of which hydroxyl group was protected by a thermo-labile tert-butoxycarbonyl (t-Boc) group, in which hydroxyazo- and hydrazone-tautomerism could be blocked. The chromophore obtained by protection with t-Boc group was exclusively present as a hydroxyazo tautomer and exhibited blue-shifted absorption spectrum compared to their parent azohydrazone tautomerizing chromophore. With this compound, we performed colorimetric anion sensing based on the deprotection-induced possible azohydrazone formation in dye chromophore subsequently resulting in naked-eye color change. Besides, the t-Boc protected chromophore could be used as a color imaging material via thermolysis of thermo-labile t-Boc groups resulting in formation of azohydrazone form with red shifted absorption.
authors.affiliation: Textile Engineering Department, Organic and Optoelectronic Materials Laboratory, Chungnam National University, Daejeon 305764, Korea.
authors.forename: Moon Soo
authors.initials: MS
authors.lastname: Choi
authors.forename: Il Hoon
authors.initials: IH
authors.lastname: Cho
authors.forename: Won Seok
authors.initials: WS
authors.lastname: Lyoo
authors.forename: Taek Seung
authors.initials: TS
authors.lastname: Lee
mesh_terms: D000042:Absorption; D000838:Anions; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003116:Color; D003124:Colorimetry / Q000379:methods*; D004952:Esters / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry; D007202:Indicators and Reagents; D008027:Light; D008956:Models, Chemical; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D013053:Spectrophotometry; D013696:Temperature; D014466:Ultraviolet Rays
chemical_list: D000838:Anions; D004952:Esters; D006835:Hydrazones; D007202:Indicators and Reagents; D009284:Naphthols; D002244:Carbon