A novel indolium salt as a highly sensitive and selective fluorescent sensor for cyanide detection in water

Promchat, Apiwat; Rashatasakhon, Paitoon; Sukwattanasinitt, Mongkol

doi:10.1016/j.jhazmat.2017.01.024

Cited by 55 publications

(19 citation statements)

References 47 publications

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“…For each product, one proton signal was observed around δ =1.8 ppm for the two homotopic methyl groups on C3 of the indolinium ring, and this resonance confirmed formation of the open merocyanine form. In contrast, closed spiropyrans are characterized by two groups of proton signals observed for the two diastereotopic methyl groups, a feature that was not observed as long as no base was added to the solution.…”

Section: Resultsmentioning

confidence: 95%

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Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four‐State Molecular Switch

Colaço¹,

Carletta

Gysel

et al. 2018

ChemistryOpen

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Direct access to the protonated merocyanine forms of two substituted spiropyrans by mechanosynthesis or sonochemistry was explored. The compounds were formed by the condensation reaction of the methyleneindolium iodide salt with salicylaldehyde derivatives. X‐ray crystallography, 1H NMR spectroscopy, ab initio geometry optimization, and absorption spectroscopy were combined to provide a better understanding of the four‐state molecular switch system in which the newly synthesized protonated merocyanines were found to play a central role. The results of this study suggest that the stability of the protonated merocyanines requires acidic conditions, as treatment with base led to the corresponding unprotonated merocyanines, which in turn spontaneously converted into photochromic closed spiropyrans.

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Section: Resultsmentioning

confidence: 95%

“…Recently, protonated merocyanines were directly synthesized by Knoevenagel condensation between substituted benzaldehydes and 1,2,3,3‐tetramethyl‐3 H ‐indolium iodide in ethanol . This procedure required long reaction times (typically 15–20 h) and was performed at a high temperature (reflux) to reach yields in the 60–85 % range.…”

Section: Resultsmentioning

confidence: 99%

Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four‐State Molecular Switch

Colaço¹,

Carletta

Gysel

et al. 2018

ChemistryOpen

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“…Therefore, these adaptive systems have the potential to revolutionize technologies such as sensors and actuators, as well as numerous biomedical applications. [38][39][40][41][42][43][44][45][46][47][48][49][50][51] For example, Kartha and co-workers found that a fluorescent organogelator could exhibit capability for trinitrotoluene (TNT) in the gel form when compared to that in the solution state. [45] They demonstrated that in n-hexane solution, the oligo (p-phenylenevinylene) perfluoroarene (OPVPF)-based gelator exhibits a green fluorescence which upon gelation turns to yellow, as shown in Figure 1B.…”

Section: Controllable Nanoassembly Of π-Conjugated Systemsmentioning

confidence: 99%

“…More interestingly, such materials can reversibly translate between liquid and solid under different stimuli conditions, which could not only be facilely utilized to detect external chemical and physical stimulations but also possess the self‐healing ability to mechanical work. Therefore, these adaptive systems have the potential to revolutionize technologies such as sensors and actuators, as well as numerous biomedical applications . For example, Kartha and co‐workers found that a fluorescent organogelator could exhibit capability for trinitrotoluene (TNT) in the gel form when compared to that in the solution state .…”

Section: Controllable Nanoassembly Of π‐Conjugated Systemsmentioning

confidence: 99%

Assembly of π‐Conjugated Nanosystems for Electronic Sensing Devices

Zhang

Wang

Cheng

et al. 2017

Adv Elect Materials

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Sensors have attracted particular attention as analytical devices because of their importance in health and security. The ability to obtain unique functions using molecular design have rapidly advanced the use of organic optoelectronic materials of π‐conjugated compounds in electronic sensing devices. A brief introduction to sensors, focusing on organic micro‐ or nanoassemblies created using state‐of‐the‐art protocols for assembly and their recent development for high‐performance electronic sensing devices, is presented.

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“…[1][2][3][4] Therefore, the developments of highly sensitive, selective, and effective sensor materials for the detection of CN − have drawn extensive attention of our eco-environments. So far, various fluorescence sensors for CN − recognition based on nucleophilic addition reaction into indolium moieties with poor aqueous solubilities [5][6][7][8][9][10] and AIE properties 11,12 have been presented. Besides, some water-soluble sensor polymers were also designed and reported to detect CN − in aqueous media.…”

Section: Introductionmentioning

confidence: 99%

Multi-Stimuli Responsive FRET Processes of Bifluorophoric AIEgens in an Amphiphilic Copolymer and Its Application to Cyanide Detection in Aqueous Media

Nhien

Chou

Cuc

et al. 2020

ACS Appl. Mater. Interfaces

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A novel amphiphilic aggregation-induced emission (AIE) copolymer, that is, poly(NIPAM-co-TPE-SP), consisting of N-isopropylacrylamide (NIPAM) as a hydrophilic unit and a tetraphenylethylene-spiropyran monomer (TPE-SP) as a bifluorophoric unit is reported. Upon UV exposure, the close form of non-emissive spiropyran (SP) in poly(NIPAM-co-TPE-SP) can be photo-switched to the open form of emissive merocyanine (MC) in poly(NIPAM-co-TPE-MC) in an aqueous solution, leading to ratiometric fluorescence of AIEgens between green TPE and red MC emissions at 517 and 627 nm, respectively, via Förster resonance energy transfer (FRET). Distinct FRET processes of poly(NIPAM-co-TPE-MC) can be observed under various UV and visible light irradiations, acid-base conditions, thermal treatments, and cyanide ion interactions, which are also confirmed by theoretical studies. The subtle perturbations of environmental factors, such as UV exposure, pH value, temperature, and cyanide ion, can be detected in aqueous media by distinct ratiometric fluorescence changes of the FRET behavior in the amphiphilic poly(NIPAM-co-TPE-MC). Moreover, the first FRET sensor polymer poly(NIPAM-co-TPE-MC) based on dual AIEgens of TPE and MC units is developed to show a very high selectivity and sensitivity with a low detection limit (LOD = 0.26 μM) toward the cyanide ion in water, which only contain an approximately 1% molar ratio of the bifluorophoric content and can be utilized in cellular bioimaging applications for cyanide detections.

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A novel indolium salt as a highly sensitive and selective fluorescent sensor for cyanide detection in water

Cited by 55 publications

References 47 publications

Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four‐State Molecular Switch

Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four‐State Molecular Switch

Assembly of π‐Conjugated Nanosystems for Electronic Sensing Devices

Multi-Stimuli Responsive FRET Processes of Bifluorophoric AIEgens in an Amphiphilic Copolymer and Its Application to Cyanide Detection in Aqueous Media

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