A novel colorimetric and fluorescent sensor for cyanide anions detection based on triphenylamine and benzothiadiazole

Zhang, Qisong; Zhang, Jian; Zuo, Hujin; Wang, Chengyun; Shen, Yongjia

doi:10.1016/j.tet.2016.01.019

Cited by 67 publications

(17 citation statements)

References 25 publications

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“…Usually, receptors for anions are charged systems capable of electrostatic interaction with anions [ 1 , 44 – 45 ] or neutral systems using other types of interactions, such as donor–acceptor interactions, hydrogen bonds, hydrophobic effects, etc. [ 46 – 57 ]. Modified macrocycles with the amide fragments at the lower rim can form complexes with the anions by hydrogen bonds of the amide group with the guest.…”

Section: Resultsmentioning

confidence: 99%

p-tert-Butylthiacalix[4]arenes functionalized by N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide fragments: synthesis and binding of anionic guests

Vavilova

Stoikov

2017

Beilstein J. Org. Chem.

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New p-tert-butylthiacalix[4]arenes, which are mono-, 1,2-di- and tetrasubstituted at the lower rim containing N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide groups in cone and partial cone conformations have been synthesized. Their complexation ability towards a number of tetrabutylammonium salts n-Bu4NX (X = F−, Cl−, Br−, I−, CH3CO2 −, H2PO4 −, NO3 −) was studied by UV spectroscopy. The effective receptor for the anions studied as well as selective receptors for F−, CH3CO2 − and H2PO4 − ions, which based on the synthesized thiacalix[4]arenes, have been obtained. It was shown that p-tert-butylthiacalix[4]arene tetrasubstituted at the lower rim by N-(4’-nitrophenyl)acetamide moieties bonded to the anions studied with association constants within the range of 3.55 × 103–7.94 × 105 M−1. Besides, the binding selectivity for F−, Cl−, CH3CO2 −, and H2PO4 − anions against other anions was in the range of 4.1–223.9. Substituting one or two fragments in the macrocycle with N,N-diethylacetamide groups significantly reduces the complexation ability of the receptor. In contrast to the 1,3-disubstituted macrocycle containing two N-(4’-nitrophenyl)acetamide moieties, the 1,2-disubstituted thiacalix[4]arene, which contains only one such fragment and a N,N-diethylacetamide moiety, selectively binds F− anions.

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Section: Resultsmentioning

confidence: 99%

p-tert-Butylthiacalix[4]arenes functionalized by N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide fragments: synthesis and binding of anionic guests

Vavilova

Stoikov

2017

Beilstein J. Org. Chem.

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“…4) based on triphenylamine and benzothiadiazole. 35 The sensing properties were studied in THF/H 2 O solution (99 : 1, v/v). With the gradual addition of CN − ions, the absorption band at 521 nm decreased and formation of a new band was found at 450 nm.…”

Section: Fluorescent Probes Based On a Triphenylamine Platform For An...mentioning

confidence: 99%

Triphenylamine-based small-molecule fluorescent probes

2022

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“…In recent years, some fluorescent probes with dicyanovinyl moieties for detecting cyanide anions have been reported [42,43,44,45,46,47]. Consequently, we hypothesized that triphenylamine-based thiophene dicyanovinyl compounds could be applied to selectively detect cyanide anion.…”

Section: Introductionmentioning

confidence: 99%

“…Triphenylamine-based thiophene dicyanovinyl compounds, which contain an electron-donating triphenylamine moiety and a strong electron-withdrawing dicyanovinyl group, were reported as red-emitting fluorophores with large Stokes shifts [ 41 ]. In recent years, some fluorescent probes with dicyanovinyl moieties for detecting cyanide anions have been reported [ 42 , 43 , 44 , 45 , 46 , 47 ]. Consequently, we hypothesized that triphenylamine-based thiophene dicyanovinyl compounds could be applied to selectively detect cyanide anion.…”

Section: Introductionmentioning

confidence: 99%

A Biocompatible Colorimetric Triphenylamine- Dicyanovinyl Conjugated Fluorescent Probe for Selective and Sensitive Detection of Cyanide Ion in Aqueous Media and Living Cells

Zheng

Song

et al. 2017

Sensors

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A colorimetric and turn-on fluorescent probe 1 bearing triphenylamine-thiophene and dicyanovinyl groups has been synthesized and used to detect cyanide anion via a nucleophilic addition reaction. Probe 1 exhibited prominent selectivity and sensitivity towards CN− in aqueous media, even in the presence of other anions such as S2−, HS−, SO32−, S2O32−, S2O82−, I−, Br−, Cl−, F−, NO2−, N3−, SO42−, SCN−, HCO3−, CO32− and AcO−. Moreover, a low detection limit (LOD, 51 nM) was observed. In addition, good cell membrane permeability and low cytotoxicity to HeLa cells were also observed, suggesting its promising potential in bio-imaging.

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A novel colorimetric and fluorescent sensor for cyanide anions detection based on triphenylamine and benzothiadiazole

Cited by 67 publications

References 25 publications

p-tert-Butylthiacalix[4]arenes functionalized by N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide fragments: synthesis and binding of anionic guests

p-tert-Butylthiacalix[4]arenes functionalized by N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide fragments: synthesis and binding of anionic guests

Triphenylamine-based small-molecule fluorescent probes

A Biocompatible Colorimetric Triphenylamine- Dicyanovinyl Conjugated Fluorescent Probe for Selective and Sensitive Detection of Cyanide Ion in Aqueous Media and Living Cells

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