A highly sensitive “ON–OFF–ON” dual optical sensor for the detection of Cu(<scp>ii</scp>) ion and triazole pesticides based on novel BODIPY-substituted cavitand
İpek Ömeroğlu, Süreyya Oğuz Tümay, Saad Makhseed, Ali Husain, Mahmut Durmuş
Abstract
The synthesis with full structural characterization including elemental analysis and 1H, 13C, 11B and 19F NMR, FT-IR and MALDI-TOF spectral data, along with the florescence sensing behavior of a new resorcin[4]arene cavitand 3 bearing multiple BODIPY sites achieved by the Cu-catalyzed azide-alkyne cycloaddition (CuAAC) is being reported. The spatial orientation of multiple BODIPY-1,2,3-triazole arms based on the macrocyclic rigid core is of great interest since the resulting structure has been utilized as a fluorescent chemosensor for numerous metal cations. In particular, a remarkable decrease in the fluorescence emission towards Cu(ii) ions, i.e., "turn-off" response, has been obtained giving rise to an optical sensor for the detection of triazole fungicides, namely tebuconazole, triadimenol, triadimefon, i.e. "turn-on" response. Such a molecular system, hence, can be feasibly applied as a dual optical sensor, i.e. "a turn-on-off-on" system, for dangerous contaminants such as heavy metals and pesticides.