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Synthesis and Recognition Properties of Rhodamin Derivative Based Metal Ion Probes

Author: LiFangFang
Tutor: TangLiJun
School:
Course: Organic Chemistry
Keywords: recognition chemosensors colorimetry fluorescence copper ion mercury ferricion
CLC: O621.3
Type: Master's thesis
Year: 2012
Downloads: 177
Quote: 0
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Abstract


Recently, the development of new artificial chemosensors for the recognition ofphysiologically and environmentally important analytes has attracted considerable attention.Among the various detection methods available, UV–vis and fluorescence spectroscopy stillremain the most frequently used modes due to their high sensitivity and easy operational use.Rhodamines are an important class of fluorogenic and chromogenic probes, which are the idealplatforms for development of chemosensors for specific heavy and transition metal ions. Theyhave excellent spectroscopic properties such as long-wavelength emission, high fluorescencequantum yield, and large molar extinction coefficient. The spirolactam form is basically colorless,while the metal induced ring-opened amide form gives rise to strong absorption within thevisible range, this feature provides a vital path way for colorimetric detection of metal ions. wedesigned and synthesized ssome new rhodamine B baed chemosensors, for colorimetric andfluorogenic recognition of Cu2+、Hg2+and Fe3+.The details are as follows:1. A new rhodamine-based sensor Rh1was designed and synthesized by incorporatingrhodamine B and benzimidazole moiety. Sensor Rh1exhibits high selectivity and sensitivity toCu2+in CH3CN-water solution （HEPES buffer, pH=7.0） with an obvious color change fromcolorless to pink. Other metal ions such as Hg2+, Ag+, Pb2+, Sr2+, Ba2+, Cd2+, Ni2+, Co2+, Fe2+,Mn2+, Zn2+, Ce3+, Mg2+, K+and Na+had no such color change and have no significant influenceon Cu2+recognition process. The interaction of Cu2+and sensor Rh1was proven to adopt a1:1binding stoichiometry and the recognition process is reversible.2. The first novel rhodamine B based sensor, rhodamine B hydrazide methyl5-formyl-1H-pyrrole-2-carboxylate Schiff base Rh2capable of detecting both Cu2+and Hg2+using two different detection modes has been designed and synthesized. The metal ion inducedoptical changes of Rh2were investigated in MeOH:H2O （3:1） HEPES buffered solution at pH7.4. Sensor2exhibits selective colorimetric recognition of Cu2+and fluorogenic recognition ofHg2+with UV–vis and fluorescence spectroscopy, respectively. Moreover, both of the Cu2+andHg2+recognition processes are proven to be hardly influenced by other coexisting metal ions.3. A new rhodamine B-coumarin conjugate Rh3capable of recognize both Cu2+and Fe3+using two different detection modes have been designed and synthesized. The metal ion inducedoptical changes of Rh3were investigated in CH3CN-H2O （1:1, v/v, HEPES50mM, pH=7.0）solution. Sensor Rh3exhibits selective colorimetric recognition of Cu2+and fluorescent recognition of Fe3+with UV-vis and fluorescence spectroscopy, respectively. Moreover, both ofthe Cu2+and Fe3+recognition processes are proven to be barely interfered by other coexistingmetal ions.

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