Imidazoanthraquinone Derivatives for the Chromofluorogenic Sensing of Basic Anions and Trivalent Metal Cations

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• 作者：Cristina Mar铆n-Hern谩ndez ; Luis E. Santos-Figueroa ; Mar铆a E. Moragues ; M. Manuela M. Raposo ; Rosa M. F. Batista ; Susana P. G. Costa ; Teresa Pardo ; Ram贸n Mart铆nez-M谩帽ez ; F茅lix Sancen贸n
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：November 21, 2014
• 年：2014
• 卷：79
• 期：22
• 页码：10752-10761
• 全文大小：576K
• ISSN：1520-6904

文摘

Four imidazoanthraquinone derivatives (2a鈥?b>d) were synthesized and characterized and their coordination behavior against selected anions and cations tested. Acetonitrile solutions of probes showed charge-transfer absorptions in the 407鈥?65 nm range. The four probes emitted in the 533鈥?71 nm interval. The recognition ability of 2a鈥?b>d was evaluated in the presence of F^{鈥?/sup>, Cl鈥?/sup>, Br鈥?/sup>, I鈥?/sup>, OCN鈥?/sup>, BzO鈥?/sup>, ClO₄鈥?/sup>, AcO鈥?/sup>, HSO₄鈥?/sup>, H₂PO₄鈥?/sup>, and CN鈥?/sup>. Only F鈥?/sup>, AcO鈥?/sup>, and H₂PO₄鈥?/sup> induced a new red-shifted absorption band that was attributed to a deprotonation process involving the amine moiety of the imidazole ring. Moreover, upon increasing quantities of F鈥?/sup>, AcO鈥?/sup>, and H₂PO₄鈥?/sup>, moderate quenching was induced in the emission of 2a鈥?b>d together with the appearance of a new red-shifted band. The UV鈥搗isible and emission behavior of the four probes in the presence of Cu2+, Co2+, Mg2+, Fe3+, Ba2+, Fe2+, Ni2+, Ca2+, Zn2+, Pb2+, Cd2+, Cr3+, Al3+, K+, and Li+ was also assessed. Only addition of Fe3+, Cr3+, and Al3+ caused a new blue-shifted band in 2a鈥?b>d that was ascribed to a preferential coordination with the acceptor part of the probes. Moreover, an important quenching of the emission was observed which was ascribed to the interaction between these trivalent cations and 2a鈥?b>d.}