Triazole-conjugated spiropyran: synthesis, selectivity toward Cu(II), and binding study. Issue 44 (28th October 2015)

• Record Type: Journal Article
• Authors: Kim, Inwon; Jeong, Dong-Cheol; Lee, Minhe; Khaleel, Zinah Hilal; Satheeshkumar, Chinnadurai; Song, Changsik
• Is Part Of: Tetrahedron letters. Volume 56:Issue 44(2015)
• Page Start: 6080
• Page End: 6084
• Publication Date: 2015-10-28
• Subjects: Spiropyran -- Merocyanine -- 1, 2, 3-Triazole -- Sensor -- Copper selectivity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.055
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Easy experimental procedures. Cheap chemicals were used to obtain the selective Cu(II) sensor. Naked eye detection. Without external stimuli Cu(II) selectively sensed through spiropyran to merocyanine open form. Abstract: Triazole-conjugated spiropyran was synthesized by Cu(I)-catalyzed azide–alkyne cycloaddition and its metal sensing properties were investigated. Color changes were observed upon the formation of metal complex between the spiropyran and Cu 2+, which was found to be selective for Cu 2+ ions among Co 2+, Hg 2+, Li +, Mg 2+, Ni 2+, Zn 2+, Cd 2+, and Cu 2+ ions. Moreover, because of the color change, the complex could be detected by the naked eye. An interesting two-stage metal binding mechanism was observed for the sensing process. First, a metal cation brought the two 1, 2, 3-triazoles together. Second, the Cu 2+ ion was selectively sensed by the conversion of the spiropyran to the merocyanine form.