Coumarin–Spiropyran Dyad with a Hydrogenated Pyran Moiety for Rapid, Selective, and Sensitive Fluorometric Detection of Cyanide Anion

Shiraishi, Yasuhiro; Nakamura, Masaya; Hayashi, Naoto; Hirai, Takayuki

doi:10.1021/acs.analchem.6b01279

Cited by 75 publications

(35 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Another significant anion to detect is the cyanide anion, which is toxic towards humans and the environment [ 16 ]. In this sense, extensive methods and probes have been developed for the qualitative and quantitative detection of these anions [ 14 , 17 , 18 , 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorescent “Turn-Off” Detection of Fluoride and Cyanide Ions Using Zwitterionic Spirocyclic Meisenheimer Compounds

et al. 2017

View full text Add to dashboard Cite

Stable zwitterionic spirocyclic Meisenheimer compounds were synthesized using a one-step reaction between picric acid and diisopropyl (ZW1) or dicyclohexyl (ZW3) carbodiimide. A solution of these compounds displays intense orange fluorescence upon UV or visible light excitation, which can be quenched or “turned-off” by adding a mole equivalent amount of F− or CN− ions in acetonitrile. Fluorescence is not quenched in the presence of other ions such as Cl−, Br−, I−, NO2−, NO3−, or H2PO4−. These compounds can therefore be utilized as practical colorimetric and fluorescent probes for monitoring the presence of F− or CN− anions.

show abstract

Section: Introductionmentioning

confidence: 99%

Fluorescent “Turn-Off” Detection of Fluoride and Cyanide Ions Using Zwitterionic Spirocyclic Meisenheimer Compounds

et al. 2017

View full text Add to dashboard Cite

show abstract

“…15,16 Among the various sensors, uorescent chemosensors present numerous advantages, including high sensitivity, low cost, and easy operation. [17][18][19] Several uorescent chemosensor systems for CN À detection reported to date are based on the mechanism of coordination, [20][21][22][23][24] hydrogen-bonding interactions, [25][26][27] nucleophilic addition reactions, [28][29][30][31][32][33][34][35][36] sonogashira cross-coupling reaction [37][38][39] and so on. However, most of the CN À sensors oen employ sophisticated structures and require complicated synthetic steps and high temperature or a long reaction time for detection of CN À .…”

Section: Introductionmentioning

confidence: 99%

A benzimidazole functionalized NDI derivative for recyclable fluorescent detection of cyanide in water

Lin

Zheng

et al. 2017

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…These include colorimetric, fluorimetric, chromatographic, and electrochemical analyses . Among those methods for cyanide detection, optical methods based on absorption and fluorescence spectroscopy are relatively simple, inexpensive, and sensitive . A number of organic sensors for cyanide anion have been designed and synthesized.…”

mentioning

confidence: 99%

Detection of Cyanide Anion by Zinc Porphyrin–Spiropyran Dyad

Kho

Hur

Shin

2016

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

Cyanide is extremely toxic to living organisms including humans. Cyanide prevents oxygen uptake by binding to hemoglobin, myoglobin, and cytochromes. 1,2 It strongly binds to the iron constituent of cytochrome c, prevents transport of electrons from cytochrome c to oxygen, and inhibits mitochondrial energy production.The uses of cyanide are widespread in the chemical industry, gold mining, electroplating, case hardening of iron and steel, photographic applications, and organic chemicals and plastics manufacturing. 3 Moreover, cyanide is found throughout nature in more than 2000 plants and in substantial amounts in certain fruit seeds. 4 In plants, cyanides act as a natural self-defense mechanism against animal predation. Long-term consumption of cyanide-containing foods, such as cassava root or apricot seeds, may lead to cyanide poisoning. The maximum permissive level of cyanide in drinking water was reported at 1.9 μM by the World Health Organization (WHO). 5 Versatile methods of the sensitive and selective detection for cyanide anion to monitor toxic cyanide have been developed. These include colorimetric, fluorimetric, chromatographic, and electrochemical analyses. 6,7 Among those methods for cyanide detection, optical methods based on absorption and fluorescence spectroscopy are relatively simple, inexpensive, and sensitive. 8,9 A number of organic sensors for cyanide anion have been designed and synthesized. Absorption and/or fluorescence spectra of these sensors are changed by forming coordination complex or bonding covalently with cyanide. Compared with other anions, cyanide anion has some characteristic properties, such as its strong nucleophilicity and high binding affinity toward metal ions, and is superior and useful for the development of the sensors. Both covalent bond-based sensors and coordination complex-based sensors have been developed for cyanide detection. 6 Spiropyran derivatives have been extensively studied as typical photochromic molecules. 10,11 The colorless nonfluorescent spiropyran form is converted into colored fluorescent merocyanine form upon ultraviolet (UV) irradiation. The merocyanine form reverts into the spiropyran form upon exposure to visible light or thermal energy. Spiropyran has been reported as a selective, sensitive, and reproducible cyanide anion receptor, based on the covalent bond formation between spiropyran and nucleophilic cyanide anion. 9,12 UV irradiation of colorless spiropyran with cyanide anion results in the formation of yellow-colored merocyanine-cyanide adduct (absorbed at around 420 nm) by nucleophilic addition of cyanide anion to merocyanine (absorbed at around 520 nm) formed by photochemical ring-opening of spiropyran. Colorless spiropyran is reproduced from merocyanine-cyanide adduct by irradiation with visible light.Metalloporphyrins are intense-colored molecules that display a wavelength shift of Soret absorption band with different ligands. 13,14 Many metalloporphyrins are useful cyanide sensors because cyanide has high affinity for many metals in m...

show abstract

Coumarin–Spiropyran Dyad with a Hydrogenated Pyran Moiety for Rapid, Selective, and Sensitive Fluorometric Detection of Cyanide Anion

Cited by 75 publications

References 51 publications

Fluorescent “Turn-Off” Detection of Fluoride and Cyanide Ions Using Zwitterionic Spirocyclic Meisenheimer Compounds

Fluorescent “Turn-Off” Detection of Fluoride and Cyanide Ions Using Zwitterionic Spirocyclic Meisenheimer Compounds

A benzimidazole functionalized NDI derivative for recyclable fluorescent detection of cyanide in water

Detection of Cyanide Anion by Zinc Porphyrin–Spiropyran Dyad

Contact Info

Product

Resources

About