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

Zhao, Jiang-Lin; Tomiyasu, Hirotsugu; Wu, Chong; Cong, Hang; Zeng, Xi; Rahman, Shofiur; Georghiou, Paris E.; Hughes, David L.; Redshaw, Carl; Yamato, Takehiko

Abstract

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.

Citation

Zhao, J.-L., Tomiyasu, H., Wu, C., Cong, H., Zeng, X., Rahman, S., Georghiou, P. E., Hughes, D. L., Redshaw, C., & Yamato, T. (2015). Synthesis, crystal structure and complexation behaviour study of an efficient Cu2+ ratiometric fluorescent chemosensor based on thiacalix[4]arene. Tetrahedron, 71(45), 8521-8527. https://doi.org/10.1016/j.tet.2015.09.038

• Journal Article Type: Article
• Acceptance Date: Sep 16, 2015
• Online Publication Date: Sep 16, 2015
• Publication Date: Oct 11, 2015
• Deposit Date: Jan 19, 2016
• Publicly Available Date: Nov 23, 2017
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 71
• Issue: 45
• Pages: 8521-8527
• DOI: https://doi.org/10.1016/j.tet.2015.09.038
• Keywords: Organic Chemistry; Biochemistry; Drug Discovery
• Public URL: https://hull-repository.worktribe.com/output/384231
• Publisher URL: http://www.sciencedirect.com/science/article/pii/S0040402015300661
• Additional Information: Authors' accepted manuscript of an article published in Tetrahedron, 2015, v.71 issue 45.
• Contract Date: Nov 23, 2017