A highly selective fluorescent chemosensor for Ag+ based on calix[4]arene with lower-rim proximal triazolylpyrenes

Wang, Nae Jen; Sun, Chung‐Ming; Chung, Wen‐Sheng

doi:10.1016/j.snb.2012.06.014

Cited by 47 publications

(20 citation statements)

References 36 publications

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“…It is known that these compounds show anti-inflammatory, antiviral, antimicrobial and antidepressant activities [1]. In addition, 1,2,4-triazole derivatives are potential chemosensors for the determination of many metal cations [2][3][4][5][6][7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Çoruh

Ustabaş

Akçay

et al. 2016

Maced. J. Chem. Chem. Eng.

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In this study, 4-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile was synthesized and its molecular structure was characterized by means of FT-IR and X-ray diffraction methods. The crystal is monoclinic and belongs to the P21/n space group. There are three weak intermolecular C-H…N type hydrogen bonds in the molecular structure. The geometrical parameters, vibration frequencies, HOMO-LUMO energies, and molecular electrostatic potential (MEP) map of the compound (3) in ground state were calculated by using density functional theory (DFT/B3LYP) with the 6-311G(d) basis set. Calculated geometrical parameters were compared with X-ray diffraction geometric parameters. On the other hand, theoretical and experimental FT-IR results were also compared.Keywords: crystal structure; 1,2,4-triazole; DFT calculations; molecular electrostatic potential; frontier orbitals ЕКСПЕРИМЕНТАЛНИ И ТЕОРЕТСКИ ИСПИТУВАЊА НА 4-[(4-МЕТИЛ-5-ФЕНИЛ-4H1,2,4-ТРИАЗОЛ-3-ИЛ)СУЛФАНИЛ]БЕНЗЕН-1,2-ДИКАРБОНИТРИЛВо ова истражување беше синтетизиран 4-[(4-метил-5-фенил-4Н1,2,4-триазол-3-ил)сул-фанил]бензен-1,2-дикарбонитрил, а неговата структура беше карактеризирана со помош на FT-IR и рендгенска дифракција. Кристалот е моноклиничен и припаѓа на просторната група P21/n. Во молекулската структура постојат три слаби интермолекулски водородни врски од типот на C-H…N. Геометриските параметри, вибрациските фреквенции, енергиите на HOMO-LUMO и мапата на молекулскиот електростатички потенцијал (MEP) на соединението (3) во основна состојба беа пресметани со теоријата на функционалот на густината (DFT/B3LYP) и основен сет 6-311G(d). Пресметаните геометриски параметри беа споредени со геометриските параметри добиени со рендгенската дифракција. Исто така беа споредени и теоретските и експерименталните резултати добиени со FT-IR.Клучни зборови: кристална структура; 1,2,4-триазол; DFT пресметки; молекулски електростатички потенцијал; гранични орбитали U. Çoruh, R. Ustabaş, H. T. Akçay, E. Menteşe, E. M. V. Lopez Maced.

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Section: Introductionmentioning

confidence: 99%

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Çoruh

Ustabaş

Akçay

et al. 2016

Maced. J. Chem. Chem. Eng.

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“…As one of highly toxic heavy metal ions, the excess silver ions causes bioaccumulation and toxicity, 1 inactivation of sulfhydryl enzymes, 2 and irreversible darkening of the skin. [4][5][6] Few literatures have reported fluorescent sensors based on conjugate polymers for silver-ion detection. 3 In the presence of moisture, oxidation of Ag-NPs results in the release of Ag + ions.…”

Section: Introductionmentioning

confidence: 99%

“…30 Although the polymers showed excellent sensitivities when used as fluorescent chemosensor for metal ions, no selectivity was observed: the polymers showed similar quenching efficiencies for Ni 2+ , Cu 2+ , Pb 2+ , Zn 2+ , Hg 2+ , and Ag + . 6,7 The design and synthesis of highly sensitive and selective system for the determination of trace amount of silver ions remains a challenge. 6,7 The design and synthesis of highly sensitive and selective system for the determination of trace amount of silver ions remains a challenge.…”

Section: Introductionmentioning

confidence: 99%

Polytriazole bridged with 2,5-diphenyl-1,3,4-oxadiazole moieties: a highly sensitive and selective fluorescence chemosensor for Ag⁺

Cao

Pei

et al. 2015

RSC Adv.

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ARTICLEThis journal is Fluorescent conjugated polytriazoles (FCP 1 -4) containing both 2,5-diphenyl-1,3,5oxadiazole (OXD) and 1,2,3-triazole moieties in the main chain were synthesized from aromatic diazide (1) and dialkynes (2 -5) via click polymerization, respectively. In the polymers, OXDs (fluorophores) and triazole rings (generated via CuAAC acting as metal ion ligands) comprise a fluorescent system. The polytriazoles displayed relatively strong emission with quantum yield in a range of 0.20 -0.28 at room temperature in DMF. The study on their ion-responsive properties showed that, although all four FCPs have good selectivity for Ag + , the intergation of bulky alkoxy side groups (methoxy for FCP 2, hexyloxy for FCP 3 and 2ethylhexyloxy for FCP 4) to the main chain of the polytriazoles decreased their sensitivity for Ag + via alteration of polymer aggregation status and electron density of the main chain. Thus FCP 1 is highly sensitive for Ag + , where its K sv is as high as 1.44 × 10 5 M -1 and its lowest detection limit is in the ppb range (4.22 × 10 -7 M). This study provides an efficient click approach to the synthesis of a novel fluorescence sensor for Ag + detection, which could expand the application of click polymerization in designing fluorescence sensor based on triazole unit. at λex = 323 nm in DMF at room temperature in the presence of metal ions (10 equiv. each, except Ag + , which was 1.0 equiv.).

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“…However, the most important clue is the great sensitivity of fluorophore to microenvironment changes, providing detailed information about the properties of the investigated system (like micropolarity, microviscosity). By tailoring the fluorophore structure (derivatization, attaching a lateral chain, immobilizing on a polymer chain) one obtains suitable chemosensors for biological, environmental or other purposes [6][7][8][9][10][11]. Depending on application, the fluorophore can be probe or label.…”

Section: Introductionmentioning

confidence: 99%

Comparing the spectral properties of pyrene as free molecule, label and derivative in some colloidal systems

Băran¹,

Stîngă²,

Anghel³

et al. 2014

Sensors and Actuators B: Chemical

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A highly selective fluorescent chemosensor for Ag+ based on calix[4]arene with lower-rim proximal triazolylpyrenes

Cited by 47 publications

References 36 publications

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Polytriazole bridged with 2,5-diphenyl-1,3,4-oxadiazole moieties: a highly sensitive and selective fluorescence chemosensor for Ag⁺

Comparing the spectral properties of pyrene as free molecule, label and derivative in some colloidal systems

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A highly selective fluorescent chemosensor for Ag+ based on calix[4]arene with lower-rim proximal triazolylpyrenes

Cited by 47 publications

References 36 publications

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Polytriazole bridged with 2,5-diphenyl-1,3,4-oxadiazole moieties: a highly sensitive and selective fluorescence chemosensor for Ag+

Comparing the spectral properties of pyrene as free molecule, label and derivative in some colloidal systems

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Polytriazole bridged with 2,5-diphenyl-1,3,4-oxadiazole moieties: a highly sensitive and selective fluorescence chemosensor for Ag⁺