Synthesis of a Phenazine‐Based 1, 2, 3‐Triazole from Naturally Occurring Naphthoquinone Designed as a Probe for Cd2+ Ions. Issue 4 (23rd December 2014)

• Record Type: Journal Article
• Authors: Jardim, Guilherme A. M.; Calado, Hállen D. R.; Cury, Luiz A.; da Silva Júnior, Eufrânio N.
• Is Part Of: European journal of organic chemistry. Issue 4(2015)
• Page Start: 703
• Page End: 709
• Publication Date: 2014-12-23
• Subjects: Sensors -- Cadmium -- Fluores­cent probes -- Click chemistry -- Quinones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403011
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The synthesis of a phenazine‐based 1, 2, 3‐triazole luminescent probe was successfully accomplished from the available natural product lapachol, which was easily extracted from the heartwood of Tabebuia sp. (Tecoma). Photophysics and fluorescence studies were conducted by using the probe in the presence of metal ions (Cd 2+, Ca 2+, Co 2+, Cu 2+, Fe 3+, Hg 2+, Mg 2+, Na +, Ni 2+, Ag +, Pb 2+, Zr 2+, and Zn 2+ as their chloride salts with the exceptions of silver and lead that were used as acetates). The probe was able to detect Cd 2+ ions in H2 O/CH3 CN (8.5:1.5 v / v ) medium. Studies performed with the sensor in a solution of cadmium chloride resulted in a green color after ultraviolet excitation, but for most metals blue color was observed, which could be detected by the naked eye. This is the first report of a lapachol, an accessible naphthoquinoidal compound, having been used to prepare a probe to detect the heavy metal cadmium. Abstract : In this study, the synthesis of a phenazine luminescent probe obtained from the natural product lapachol is described. The compound is modified through click chemistry to generate a binding site for Cd 2+ ions. Photophysics and fluorescence studies are conducted to prove the efficiency of this sensor.