Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies

Kowser, Zannatul; Jin, Cheng-Cheng; Jiang, Xuekai; Rahman, Shofiur; Georghiou, Paris E.; Ni, Xin-Long; Zeng, Xi; Redshaw, Carl; Yamato, Takehiko

Abstract

A new fluorescent chemosensor L1, pyrene containing long chain Schiff base derivative in 1-position has been synthesized. Similarly, the receptors L2 and L3 are also designed in order to compare the binding ability for detection of Cu2+. The receptors exhibit very weak fluorescence (Φ = 0.01) due to the photoinduced electron transfer (PET). Upon addition of 10 equiv. of Cu2+, the emission intensity of ligands L1 and L2 are increased 65-fold (Φ = 0.31) and 25-fold (Φ = 0.08) in CH3CN/CH2Cl2 solvents system respectively. NMR titration experiments, spectroscopic and DFT computational studies confirmed the binding phenomena and sensitivity of Cu2+.

Citation

Kowser, Z., Jin, C.-C., Jiang, X., Rahman, S., Georghiou, P. E., Ni, X.-L., Zeng, X., Redshaw, C., & Yamato, T. (2016). Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies. Tetrahedron, 72(30), 4575-4581. https://doi.org/10.1016/j.tet.2016.06.017

• Journal Article Type: Article
• Acceptance Date: Jun 6, 2016
• Online Publication Date: Jun 7, 2016
• Publication Date: Jul 28, 2016
• Deposit Date: Dec 19, 2016
• Publicly Available Date: Dec 19, 2016
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 72
• Issue: 30
• Pages: 4575-4581
• DOI: https://doi.org/10.1016/j.tet.2016.06.017
• Keywords: Pyrene-based Schiff base derivatives; Fluorescent turn-on sensor; High selectivity and sensitivity; DFT computational studies
• Public URL: https://hull-repository.worktribe.com/output/446192
• Publisher URL: http://www.sciencedirect.com/science/article/pii/S0040402016305300
• Additional Information: This article is maintained by: Elsevier; Article Title: Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies; Journal Title: Tetrahedron; CrossRef DOI link to publisher maintained version: http://dx.doi.org/10.1016/j.tet.2016.06.017; Content Type: article; Copyright: © 2016 Elsevier Ltd. All rights reserved.
• Contract Date: Dec 19, 2016