Polyacetylenes as Colorimetric and Fluorescent Chemosensor for Anions

Sakai, Ryosuke; Satoh, Toshifumi; Kakuchi, Toyoji

doi:10.1080/15583724.2016.1144613

Cited by 32 publications

(21 citation statements)

References 87 publications

(90 reference statements)

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“…The novel compounds were characterized by FT-IR, 1 H NMR and 13 C NMR spectroscopy, all the characteristic absorption bands and signals were detected.…”

Section: Resultsmentioning

confidence: 99%

“…1 H, 13 C NMR spectra were recorded on a Bruker Avance III spectrometer at 400 MHz using DMSO-d 6 with TMS reference. FT-IR spectra were recorded on Tensor II, Bruker-Optics FT-IR spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

“…[1][2][3][4][5][6] The molecular sensing of anions is one of the most important topics in supramolecular chemistry [7][8][9][10] , the ability of the molecular sensor to form noncovalent interactions, particularly selective hydrogen bonding interactions with the analytes is fundamental and crucial point based on which molecular sensors are designed. Molecules that containing functional groups such as amide [11][12][13][14] , urea [15][16] and hydroxyl 17 have been openly used to sense anions by hydrogen bonding interactions for numerous important anionic analytes 18 , on other hand, Schiff bases have been utilized to develop chemosensors with selective sensitivity to anions, especially ones containing phenolic groups in their structures are used in one of strategies of designing sensor for anions due to the ability of the phenolic -OH group to interact with anions by hydrogen bonding. 19 Among the various anions, acetate has attracted researcher to develop molecular sensors to detect it selectively, acetate performs important roles in organic, environmental and biological processes such as biocatalysis, antibodies and other cellular processes.…”

Section: Introductionmentioning

confidence: 99%

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Selective Naked-Eye Detection of Acetate by New Azo-Isonicotinohydrazide Derivatives

Makki¹,

Balakit²

2017

Orient. J. Chem

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Three new hydrazone, based on azo-isonicotinohydrazide derivatives, have been designed, synthesized and characterized by FT-IR, 1 H NMR and 13 C NMR spectroscopy. The new compounds were designed to act as selective molecular sensors for naked-eye detection of acetate anion. To study the effect of the substituent at certain position in the main structure on the selectivity of the sensor, the compounds were designed to have −CH 3 , −H or −NO 2 at that position. Solutions of different anions (F − , H 2 PO 4 − , NO 2 − , NO 3 − , Cl − , HSO 4 − , ΗCO3 − ) and AcO − were used to test the selectivity. The results revealed that the compound with electron withdrawing group (NO 2 ) interacts selectively with acetate producing a significant feasible color change which makes it considered as selective molecular sensor for naked-eye detection of acetate. The dissociation constant for AcO − with the new sensor was also determined.

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“…The novel compounds were characterized by FT-IR, 1 H NMR and 13 C NMR spectroscopy, all the characteristic absorption bands and signals were detected.…”

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Selective Naked-Eye Detection of Acetate by New Azo-Isonicotinohydrazide Derivatives

Makki¹,

Balakit²

2017

Orient. J. Chem

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show abstract

“…Anions play an important role in biological systems, as these are the main components in maintaining the homeostasis of the body [1][2][3]. But their extensive use may cause serious health issues [4,5]. That's why, in recent years, their detection became a very important prospective for chemists and biologists and many techniques have been developed for this purpose [6,7].…”

Section: Introductionmentioning

confidence: 99%

Isatin-3-thiosemicarbazone as Chromogenic Sensor for the Selective Detection of Fluoride Anion

Rasheed

Ahmed

Faisal

et al. 2020

Heterocyclic Communications

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In this study, we describe the anion recognition ability of isatin-3-thiosemicarbazone 2, which contains two different anion recognition units i.e. isatin NH and the thiourea moiety. Both have the ability to act as proton donors. Most importantly, a significant colour change of 2 was observed (from light yellow to reddish orange) in organic medium only after the addition of the F– anion. No such colour change could be observed for any other anions including Cl–, Br–, I–, ${{\text{H}}_{2}}\text{P}{{\text{O}}_{4}}^{-},$$\text{N}{{\text{O}}_{\text{2}}}^{-},$$\text{P}{{\text{F}}_{4}}^{-}$etc. The UV-Vis spectroscopic studies also indicate the potential of this compound for selective detection of fluoride anions. 1H-NMR titrations clearly indicate the formation of the 2.F– anionic complex. The Density-functional theory (DFT) calculations are also performed to get further insights on the formation of 2.F– complex.

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“…Pendant functional groups of polyacetylenes may serve as a tool for introducing or tuning the properties of these polymers, e.g., the conductivity, photoconductivity, specific interaction with molecules or ions, luminescence, helical conformation, and side‐chain liquid crystalline character . Reactive pendant functional groups of polyacetylenes can be moreover chemically modified using various postpolymerization reactions under formation of linear or cross‐linked polymers of modified qualities.…”

Section: Introductionmentioning

confidence: 99%

Unexpectedly Facile Rh(I) Catalyzed Polymerization of Ethynylbenzaldehyde Type Monomers: Synthesis of Polyacetylenes Bearing Reactive and Easy Transformable Pendant Carbaldehyde Groups

Sedláček

Havelková

Zednı́k

et al. 2017

Macromol. Rapid Commun.

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The chain coordination polymerization of (ethynylarene)carbaldehydes with unprotected carbaldehyde groups, namely ethynylbenzaldehydes, 1-ethynylbenzene-3,5-dicarboxaldehyde, and 3-[(4-ethynylphenyl)ethynyl]benzaldehyde, is reported for the first time. Polymerization is catalyzed with various Rh(I) catalysts and yields poly(arylacetylene)s with one or two pendant carbaldehyde groups per monomeric unit. Surprisingly, the carbaldehyde groups of the monomers do not inhibit the polymerization unlike the carbaldehyde group of unsubstituted benzaldehyde that acts as a strong inhibitor of Rh(I) catalyzed polymerization of arylacetylenes. The inhibition ability of carbaldehyde groups in (ethynylarene)carbaldehydes seems to be eliminated owing to a simultaneous presence of unsaturated ethynyl groups in (ethynylarene)carbaldehydes. The reactive carbaldehyde groups make poly[(ethynylarene)carbaldehyde]s promising for functional appreciation via various postpolymerization modifications. The introduction of photoluminescence or chirality to poly(ethynylbenzaldehyde)s via quantitative modification of their carbaldehyde groups in reaction with either photoluminescent or chiral primary amines under formation of the polymers with Schiff-base-type pendant groups is given as an example.

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Polyacetylenes as Colorimetric and Fluorescent Chemosensor for Anions

Cited by 32 publications

References 87 publications

Selective Naked-Eye Detection of Acetate by New Azo-Isonicotinohydrazide Derivatives

Selective Naked-Eye Detection of Acetate by New Azo-Isonicotinohydrazide Derivatives

Isatin-3-thiosemicarbazone as Chromogenic Sensor for the Selective Detection of Fluoride Anion

Unexpectedly Facile Rh(I) Catalyzed Polymerization of Ethynylbenzaldehyde Type Monomers: Synthesis of Polyacetylenes Bearing Reactive and Easy Transformable Pendant Carbaldehyde Groups

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