Positive allosteric binding behavior of pyrene-appended triazole-modified thiacalix[4]arene-based fluorescent receptors

Tomiyasu, Hirotsugu; Shigyo, Naoki; Ni, Xin-Long; Zeng, Xi; Redshaw, Carl; Yamato, Takehiko

Abstract

The novel heteroditopic receptors 5a∼c have been synthesized, which bear a thiacalix[4]arene in the 1,3-alternate conformation. Two urea moieties possessing various aryl groups with either electron-donating or -withdrawing groups at their p-positions function as anion-binding sites. At the opposite side of the cavity are two pyrene-appended triazole rings, which act as cation-binding sites. The binding property of receptor 5c was investigated by means of 1H NMR and UV–vis spectroscopy and by fluorescence titration experiments in the presence of various transition metal cations and anions in CH2Cl2–DMSO (10:1, v/v) solution. Interestingly, it was found that receptor 5c possessing two p-nitrophenyl ureido moieties, most efficiently complexes in the urea cavity or bistriazoles; the plausible allosteric effect of receptor 5c was also investigated.

Citation

Tomiyasu, H., Shigyo, N., Ni, X.-L., Zeng, X., Redshaw, C., & Yamato, T. (2014). Positive allosteric binding behavior of pyrene-appended triazole-modified thiacalix[4]arene-based fluorescent receptors. Tetrahedron, 70(43), 7893-7899. https://doi.org/10.1016/j.tet.2014.08.068

• Journal Article Type: Article
• Acceptance Date: Aug 28, 2014
• Online Publication Date: Sep 6, 2014
• Publication Date: Oct 28, 2014
• Deposit Date: Mar 14, 2016
• Publicly Available Date: Mar 14, 2016
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 70
• Issue: 43
• Pages: 7893-7899
• DOI: https://doi.org/10.1016/j.tet.2014.08.068
• Keywords: Thiacalix[4]arene, 1,3-alternate conformation, Pyrenyl-appended triazole, Urea, Allosteric effect
• Public URL: https://hull-repository.worktribe.com/output/412946
• Publisher URL: http://www.sciencedirect.com/science/article/pii/S0040402014012745
• Additional Information: This is a description of an article which has been published in: Tetrahedron, 2014, v.70, issue 43
• Contract Date: Mar 14, 2016