Switching the Recognition Preference of Rhodamine B Spirolactam by Replacing One Atom:  Design of Rhodamine B Thiohydrazide for Recognition of Hg(II) in Aqueous Solution

Zheng, Hong; Qian, Zhen-Hua; Xu, Lei; Yuan, Fangfang; Lan, Li-Dan; Xu, Juntian

doi:10.1021/ol0529086

Cited by 360 publications

(129 citation statements)

References 8 publications

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“…2). 12 Because of the spirolactam ring, sensor 1 displayed no absorption in the visible region and gave none fluorescence. Upon addition of Hg 2+ , colorless free 1 showed a new absorption with a maximum wavelength at 561 nm (ε = 125000 M -1 cm -1 ) and took on a strong pink color which can be seen by unaided human vision.…”

Section: +mentioning

confidence: 99%

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Small-molecule Fluorescent Chemosensors for Hg2+  Ion

Zhang

Kim

2009

ANAL. SCI.

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1271 introductionMercury pollution is a global problem. 1,2 Owning to the grisly immunotoxic, genotoxic, and neurotoxic effects, mercury is considered to be a highly dangerous element by the United States Environmental Protection Agency. 3,4 For the purposes of detection and quantitative determination of mercury ions, much effort has been devoted to the development of appropriate methods that are low-cost, rapid, deft and applicable to natural environmental and biological milieus. 5,6 In contrast with many of the traditional quantitative approaches to Hg 2+ analysis that require intricate, multistep sample preparation and/or sophisticated instrumentation, fluorometric detections following the changes in the emission of light are more convenient and suitable for monitoring Hg 2+ in either natural or biological environments. 6There are multiple advantages in using fluorescence: (i) its powerful visual effects; (ii) its greater sensitivity than that of absorption spectroscopy; (iii) its simple equipment, commonly available in many scientific laboratories. 7,8 As a consequence, for fluorometric determination of Hg 2+ , a large number of fluorescent sensors including two components, an ionophore (receptor) for selective binding of the substrate and a fluorophore (transducer) for providing the means of signaling this binding, have recently been designed and synthesized. 8 This review focuses mainly on the small-molecular fluorescent chemosensors for Hg 2+ ion in organic or aqueous solution that were developed by our research laboratories and other groups in recent years. Fluorescent chemosensors in this review are divided into two sections based on the bearing fluorophore. The first section focuses on the development of rhodamine-derived Hg 2+ ion sensors, while the other section gave a brief introduction about Hg 2+ ion sensors bearing other functional fluorophores. Mechanisms generally used in explaining the response of a fluorophore to Hg 2+ binding include photoinduced electron transfer (PET), fluorescence resonance energy transfer (FRET), internal charge transfer (ICT), photoinduced charge transfer (PCT) and excimer/exciplex formation or extinction. 8,92 Rhodamine-derived hg 2+ ion SensorsNoelting and Dziewonski first reported the preparation of the rhodamine in 1905. 10 However, it was only from the 21th century that the rhodamine-B derivatives and its ring-opening reaction received a great deal of attention and have been applied as fluorescent metal ion sensors in organic and biological researches. 11As schematically shown in Fig. 1

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confidence: 99%

“…These results were attributed to the coordination in 1-Hg of Hg 2+ center wrapped by two rhodamine 1 using N and S binding sites to open its spirolactam ring. 12 Another rhodamine-based off-on fluorescent chemosensor 2 with N-tripodal structure was synthesized and reported by our group in 2007. 13 Compound 2 ( Fig.…”

Section: +mentioning

confidence: 99%

Small-molecule Fluorescent Chemosensors for Hg2+  Ion

Zhang

Kim

2009

ANAL. SCI.

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“…[20][21][22][23] To date, many fluorescent sensors for Hg 2+ have been reported. [24][25][26][27][28][29][30][31][32] However, many of these sensors are small molecules, which can only work in organic or mixed solvents, may restrict their applications in the environmental or biorelated fields due to their low water solubility and high toxicity. 33,34 To overcome these limitations, polymeric micellesbased sensors have recently attracted considerable interest owing to their excellent properties, including improved water solubility and longer in vivo circulation times, effective distribution of fluorescent dyes, etc.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Water-soluble Fluorescent Polymeric Micelles for Selective Detection of Hg2+ in Blood Serum

et al. 2017

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In this study, amphiphilic diblock copolymers were designed and synthesized via the incorporation of reversible additionfragmentation chain transfer radical polymerization (RAFT) and a subsequent grafting technique. Subsequently, Hg 2+ -sensitive water-soluble fluorescent polymeric micelles (FNs) were prepared by a reprecipitation strategy. The spectroscopic characteristics demonstrate that the fluorescein isothiocyanate (FITC) was successfully linked into the polymer. Due to the promoted reaction of desulfurization cyclization by Hg 2+ , the fluorescence of fluorescein in FNs was obviously quenched. The as-prepared FNs showed admirable Hg 2+ -sensitivity (detection limit: 54 nM), excellent water-solubility and high selectivity. In addition, FNs were successfully used to determine Hg 2+ in blood serum. We expected that the as-prepared FNs could perform potential applications in imaging, sensing, and bioanalytic chemistry.

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“…41 Thus, it is accepted that the detection of Hg 2+ at ppb levels with high selectivity can be achieved by fluorescent probes based on irreversible fluorescence reactions rather than receptor-type probes. [41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57] For the design of the irreversible fluorescent probes for Hg 2+ detection, oxymercuration reaction has been recently explored. 56,57 The design principle is quite interesting, but the technique requires high temperatures or long reaction times, especially for detecting Hg 2+ at ppb levels.…”

Section: Introductionmentioning

confidence: 99%

Determination of Mercury(II) in Aquatic Plants Using Quinoline-Thiourea Conjugates as a Fluorescent Probe

et al. 2013

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In this study, a quinoline-thiourea conjugate (1-phenyl-3-(quinoline-8-yl) thiourea, PQT) was synthesized and used as a fluorescence sensor to detect mercury ion. The observation is coincident with the well-documented phenomenon that a thiocarbonyl-containing group on a fluorochrome quenches the fluorescence due to the heavy atom effect of the S atom. The large fluorescence enhancement of PQT in the buffered MeCN-water mixture (1/1 v/v; HEPES 100 mM; pH 8.0) was caused by the Hg 2+ induced transformation of the thiourea function into a urea group. As such, protic solvents can be ascribed to hydrogen bond formation on the carbonyl oxygen to reduce the internal conversion rate. The fluorescence intensity of PQT was enhanced quantitatively with an increase in the concentration of mercury ion. The limit of detection of Hg 2+ was 7.5 nM. The coexistence of other metal ions with mercury had no obvious influence on the detection of mercury. A quinolone-thiourea conjugate was used as a fluorescent probe to detect Hg 2+ in aquatic plants and the experimental results were satisfactory.

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Switching the Recognition Preference of Rhodamine B Spirolactam by Replacing One Atom: Design of Rhodamine B Thiohydrazide for Recognition of Hg(II) in Aqueous Solution

Cited by 360 publications

References 8 publications

Small-molecule Fluorescent Chemosensors for Hg2+  Ion

Small-molecule Fluorescent Chemosensors for Hg2+  Ion

Fabrication of Water-soluble Fluorescent Polymeric Micelles for Selective Detection of Hg2+ in Blood Serum

Determination of Mercury(II) in Aquatic Plants Using Quinoline-Thiourea Conjugates as a Fluorescent Probe

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Switching the Recognition Preference of Rhodamine B Spirolactam by Replacing One Atom: Design of Rhodamine B Thiohydrazide for Recognition of Hg(II) in Aqueous Solution

Cited by 360 publications

References 8 publications

Small-molecule Fluorescent Chemosensors for Hg2+ Ion

Small-molecule Fluorescent Chemosensors for Hg2+ Ion

Fabrication of Water-soluble Fluorescent Polymeric Micelles for Selective Detection of Hg2+ in Blood Serum

Determination of Mercury(II) in Aquatic Plants Using Quinoline-Thiourea Conjugates as a Fluorescent Probe

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Small-molecule Fluorescent Chemosensors for Hg2+  Ion

Small-molecule Fluorescent Chemosensors for Hg2+  Ion