Tetraphenylethylene imidazolium macrocycle: synthesis and selective fluorescence turn-on sensing of pyrophosphate anions

Wang, Jinhua; Xiong, Jia-Bin; Zeng, Xing; Song, Song; Zhu, Zhi‐Biao; Zheng, Yan‐Song

doi:10.1039/c5ra09721e

Cited by 31 publications

(17 citation statements)

References 42 publications

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“…By itself, TPE-based imidazolium macrocycle 42 did not respond to any of the anions tested, including PPi, in a solution of 0.5% DMSO in water. However, the inclusion of one equivalent of Zn(OAc) 2 in the solution led to a large fluorescence enhancement at 472 nm in the presence of PPi [ 118 ]. Competition experiments with other anions revealed no significant changes to emission.…”

Section: Other Macrocyclic Sensorsmentioning

confidence: 99%

“… Combining Zn 2+ with either of the macrocycles 42 and 43 affords highly effective probes for pyrophosphate anion (PPi). A solution containing TPE/imidazolium macrocycle 42 and one equivalent of Zn(OAc) 2 reports PPi binding via an AIE mechanism, which gives rise to a significant fluorescence enhancement at 472 nm [ 118 ]. In a similar vein, the Zn 2+ complex of methylquinoline-substituted azamacrocycle 43 has shown exceptional selectivity and sensitivity for PPi over other phosphorous-based anions, returning a 21-fold fluorescence increase in the presence of PPi (1 equivalent) via an ICT mechanism [ 119 ].…”

Section: Figurementioning

confidence: 99%

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Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing

2017

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Small-molecule fluorescent probes play a myriad of important roles in chemical sensing. Many such systems incorporating a receptor component designed to recognise and bind a specific analyte, and a reporter or transducer component which signals the binding event with a change in fluorescence output have been developed. Fluorescent probes use a variety of mechanisms to transmit the binding event to the reporter unit, including photoinduced electron transfer (PET), charge transfer (CT), Förster resonance energy transfer (FRET), excimer formation, and aggregation induced emission (AIE) or aggregation caused quenching (ACQ). These systems respond to a wide array of potential analytes including protons, metal cations, anions, carbohydrates, and other biomolecules. This review surveys important new fluorescence-based probes for these and other analytes that have been reported over the past five years, focusing on the most widely exploited macrocyclic recognition components, those based on cyclam, calixarenes, cyclodextrins and crown ethers; other macrocyclic and non-macrocyclic receptors are also discussed.

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Section: Other Macrocyclic Sensorsmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing

2017

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“…Zheng et al synthesized imidazolium ‐ tetraphenylethylene (TPE) based macrocycle 128 showing poor emission in aqueous medium. The fluorescence emission was not induced by the addition of common inorganic anions to this solution, including pyrophosphate.…”

Section: Recognition Of Phosphates and Nucleotidesmentioning

confidence: 99%

Imidazolium Based Probes for Recognition of Biologically and Medically Relevant Anions

et al. 2016

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The imidazolium derivatives due to their positive charge possess one of the most polarized and positively charged proton at C2-H to form strong ionic hydrogen bond (also termed as double ionic hydrogen bond) with anions and also provide opportunities for anion - π interactions with electron-deficient imidazolium ring. In the present review article, imidazolium based molecular probes for their ability to recognize inorganic anions like halides, cyanide, perchlorate, carboxylic acids, phosphate, sulfate etc. and their derived molecules viz. nucleotides, DNA, RNA, surfactants, proteins, etc have been discussed. The review covers the literature published after year 2009 and has > 130 references. The previous literature has already been discussed by Yoon et al. in two review articles published in Chem. Soc. Rev. 2006 and 2010.

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“…8 Although several chemosensors have been reported for phosphate-anion sensing. 9–12 However, great difficulties remains to develop highly selective and sensitive fluorescence sensors for phosphate anions especially in aqueous environment because of disrupting of binding of solvents and competitions from other similar anions. An effective strategy to overcome those challenges is to develop chemical sensors that have multiple binding units preorganized for specific targets of interest.…”

Section: Introductionmentioning

confidence: 99%