Synthesis, crystal structure and complexation behaviour study of an efficient Cu2+ ratiometric fluorescent chemosensor based on thiacalix[4]arene

• DOI: 10.1016/j.tet.2015.09.038
• Publication Date: 2015-09-16T17:14:44Z
• Authors: Jiang-Lin Zhao; Hirotsugu Tomiyasu; Chong Wu; Hang Cong; Xi Zeng; Shofiur Rahman; Paris E. Georghiou; David L. Hughes; Carl Redshaw; Takehiko Yamato
• Keywords: Ethylene diamine

A new thiacalix[4]arene based fluorescent chemosensor L bearing two pyrenyl groups in a 1,3-alternate conformation has been synthesized, and its metal ion-binding and fluorescence-sensing properties were investigated in ethanol. The designed chemosensor L exhibited high selectivity toward Cu²⁺ ions versus the other tested metal ions with a detection limit of up to 1.44 × 10⁻⁷ M. The chemosensor L was capable of acting an efficient ratiometric fluorescent chemosensor at low ion concentration or as a fluorescence quenching type chemosensor due to the PET and heavy atom effects operating in high ionic strength solution. Further studies revealed that chemosensor L acted as a reversible sensor in the presence of Cu²⁺ and ethylenediamine.