Colorimetric anion sensing and color imaging based on catalyzed deprotection in a new azonaphthol chromophore.
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.
Choi
Moon Soo
MS
Textile Engineering Department, Organic and Optoelectronic Materials Laboratory, Chungnam National University, Daejeon 305764, Korea.
Cho
Il Hoon
IH
Lyoo
Won Seok
WS
Lee
Taek Seung
TS
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
D000838:Anions; D004952:Esters; D006835:Hydrazones; D007202:Indicators and Reagents; D009284:Naphthols; D002244:Carbon