A novel and synthetically facile coumarin-thiophene-derived Schiff base for selective fluorescent detection of cyanide anions in aqueous solution: Synthesis, anion interactions, theoretical study and DNA-binding properties

Chemchem, Meryem; Yahaya, Issah; Aydıner, Burcu; Seferoğlu, Nurgül; Doluca, Osman; Merabet, Naima; Seferoğlu, Zeynel

doi:10.1016/j.tet.2018.10.008

Cited by 48 publications

(13 citation statements)

References 80 publications

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“…Furthermore, the limits of detection (LOD) and quantification (LOQ) were determined for dyes 8 – 12 . The LOD and the LOQ were respectively found to be as follow: 73.1 μM and 244 μM for 8 , 47.2 μM and 157 μM for 9 , 47.3 μM and 158. μM for 10 , 50.9 μM and 170 μM for 11 , 33.1 μM, and 110 μM for 12 (Figures S87–S91, Supporting Information File 1 ) [ 25 ].…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, Schiff bases bearing a salicylidene moiety are also used as chemosensors for sensing of specific ions. In addition, some derivatives also show NLO activity [25,[34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, pH-sensitive dyes play a critical role in various sensor applications for easy determination of such ions. These dyes show different spectral properties upon protonation/deprotonation processes [ 23 – 25 ]. Fluorescent dyes as chemosensors offer unique merits such as low energy consumption, ease of handling, high selectivity, and notable sensitivity [ 26 – 27 ].…”

Section: Introductionmentioning

confidence: 99%

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Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Putra¹,

Çakmaz²,

Seferoğlu³

et al. 2020

Beilstein J. Org. Chem.

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Herein we report the synthesis and characterization of a new series of styryl-based push-pull dyes containing a free amino group and their Schiff base derivatives. The dyes include the dicyanomethylene group as an acceptor and different para-substituted alkylamines as donors. Morever as a proton-sensitive group a pyridin-2-yl substituent was attached to the para-position of the phenyl moiety in both series of compounds. The photophysical properties of the dyes were examined in various solvents with different polarities and showed absorption in the visible region and green-red emission with low quantum yields. The absorption and the emission maxima were shifted bathocromically by increasing the solvent’s polarity. However, there was no correlation with the polarity parameters of the solvents. The pH-sensitive properties of all prepared Schiff bases were examined against TBAOH in DMSO, via deprotonation of the OH group in the salicylidene moiety and their reverse protonation was also investigated using TFA. The Schiff bases exhibited a bathochromic shift upon the addition of TBAOH to their solutions in DMSO. Therefore, they showed potential to be utilized as colorimetric and luminescence pH sensors. The second-order nonlinear optical (NLO) responses of the dyes were measured by the electric field-induced second harmonic (EFISH) generation method. The highest μβ values were obtained for the dyes bearing the julolidine donor as 1430 × 10−48 esu (for free amino derivative) and 1950 × 10−48 esu (for Schiff base derivative), respectively. The structural and electronic properties of the dyes as well as their NLO properties were further studied using DFT calculations. The thermal stabilities of all dyes were evaluated by thermogravimetric analysis (TGA). The TGA data showed that all dyes were thermally stable up to 250 °C.

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Section: Resultsmentioning

confidence: 99%

“…Moreover, Schiff bases bearing a salicylidene moiety are also used as chemosensors for sensing of specific ions. In addition, some derivatives also show NLO activity [25,[34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Putra¹,

Çakmaz²,

Seferoğlu³

et al. 2020

Beilstein J. Org. Chem.

Self Cite

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“…Additionally, they proposed the mechanism in this study as an ICT involving di-deprotonation of the acidic OH protons in chemosensor. They also revealed in their study that the chemosensor can intercalate into dublex DNA and it can be evaluated using a DNA detection agent [20]. The chemosensors with a chromophoric group act as a powerful tool for detecting cyanide and fluoride ions in aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach

Khan

Agrawal

Ubaidullah

et al. 2019

Heliyon

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An ecofriendly itinerary for the synthesis of newly substituted chromene-3-carboxamide derivatives was undertaken to avoid impurities, usage of toxic solvents, toxic catalyst, and having improved quantitative yields. The green synthesis involves the condensation of substituted salicylaldehyde with N-(substituted)phenyl malonic acid in the presence of a base catalyst, piperidine. All reported compounds were assessed for their antimicrobial activities which clearly suggested their therapeutic implications to address antimicrobial pathogenesis. The synthesized coumarin compounds were examined for their antimicrobial activity against 7 fungal strains and 2 bacterial strains at concentration 125–1000 μg/mL. In particular, the compounds 4 and 5 showed lower minimum inhibitory concentration value (125 μg/mL) against maximum microbial strains. Further, docking of all the synthesized compounds was performed with the enzymes lanosterol 14α-demethylase and glucosamine-6-phosphate synthase and a significant binding affinity was observed which supports in vivo antimicrobial study. In addition, the thermal analysis revealed good thermal stability of compounds up to 250 °C. The compounds showed abroad absorption spectrum between 280-550 nm establishing them to be good UV absorbers.

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“…Heterocyclic compounds bearing coumarin moiety are among the well-known chromophore groups for important chromogenic/fluorogenic sensors [12]. Coumarins that are substituted at the 7-position with a diethylamino group are especially well known for their applications in chemosensor chemistry, laser dyes, fluorescent markers for amino acids, anions/cations, organic light-emitting diodes, and sensitizers in DSSCs as chromogenic and fluorochromogenic chromophores [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Coumarin-based benzilmonohydrazone as a new proton-sensitive fluorescencedye: synthesis and investigation of photophysical and acidochromic properties

Aydıner¹

2019

Turk J Chem

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Coumarin-based chromogenic and fluorogenic dye 4 was designed and synthesized. The photophysical properties of 4 were determined in solvents with different polarities. Protonation affinity was determined by adding trifluoroacetic acid (TFA) to a dichloromethane solution of dye 4 utilizing the UV-Vis and fluorescence titration methods. The protonation region was investigated by using the 1 H NMR method. Additionally, DFT and TDDFT studies were performed to support the structural and absorption spectral properties of 4.

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A novel and synthetically facile coumarin-thiophene-derived Schiff base for selective fluorescent detection of cyanide anions in aqueous solution: Synthesis, anion interactions, theoretical study and DNA-binding properties

Cited by 48 publications

References 80 publications

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach

Coumarin-based benzilmonohydrazone as a new proton-sensitive fluorescencedye: synthesis and investigation of photophysical and acidochromic properties

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