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Novel multi-responsive fluorescence switch for Hg2+ and UV/vis lights based on diarylethene-rhodamine derivative

Wang, Shuai, Ding, Haichang, Wang, Yuesong, Fan, Congbin, Liu, Gang, Pu, Shouzhi
Tetrahedron 2019 v.75 no.11 pp. 1517-1524
absorbance, chemical structure, color, fluorescence, hydrazides, hydrolysis, mercury, piperazine, rhodamines
A new multi-responsive fluorescent switch DTE-Pip-Rho 1O has been designed and synthesized in this study. For this molecule, the reactive site of spirolactam ring is far away from the diarylethene unit through the intramolecular piperazine. It exhibited high selectivity and sensitivity to Hg2+ in addition to obvious color change (colorless-pink) and fluorescence “off-on” (dark-orange) during this process. It is believed that the color change is due to Hg2+-assisted hydrolysis of rhodamine hydrazide. Therefore, the new molecule can be used as colorimentric and fluorescent chemosensor for Hg2+ with high selectivity. The detection limits of absorbance and fluorescence for Hg2+ were calculated to be 1.15 μM and 1.16 μM, respectively. The resulting DTE-Pip-Rho 1O-Hg2+ could also function as a reversible fluorescence photo-switch in response to UV/vis light owing to FRET mechanism. Moreover, it has been demonstrated that the photo-switchable system displayed excellent fatigue resistance and remarkable anti-photobleaching capability.