Fluorescent aromatic symmetrical azines: Synthesis and appraisal of their photophysical and electrochemical properties

Poojary, Sachin; Sunil, Dhanya; Kekuda, Dhananjaya; Sreenivasa, S.

doi:10.1016/j.optmat.2018.08.020

Cited by 20 publications

(6 citation statements)

References 30 publications

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“…The idea of using molecular systems exhibiting ESIPT characteristics to solar concentrators is relatively new [10,11] and is based on an increased flexibility through tailoring intermolecular interactions. However, tuning molecular aggregation in solid state by using hybrid sol-gel generated film-forming materials can be an effective way to achieve the tunable emission of such materials, and SAA can serve as a molecular model in this sense [12]. Nevertheless, among other types of fluorophore dyes, SAA display aggregation-induced emission enhancement (AIEE), which can be seen when the SAA content was increased.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Silica Hybrid Film-Forming Materials Based on Salicylaldazine

Rădiţoiu

Raduly

et al. 2020

Coatings

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Fluorescent film-forming materials were obtained by embedding salicylaldazine (SAA) in silica hybrids generated by sol–gel processes from different silane precursors in acid catalysis. Tuned local environments for the fluorophore were generated in the hosting network by modifying silica sols with organic groups through the co-condensation of tetraethylortosilicate (TEOS) and different alkoxysilanes hydrolysis products. The photophysical properties of the luminescent hybrid films were studied in direct relationship with structural, textural, and surface properties and based on interactions between SAA species and the silica hosting network. Film-forming materials were studied in order to determine differences in absorption and fluorescence emission due to the environments around the fluorophore. The variations recorded in the fluorescence emission spectra of the hybrid films were related to interactions established between the fluorophore species and their sterically hindered surroundings of the host hybrid silica, where free molecular motions are restricted. The influence of the type and amount of network modifier and of the fluorophore loading on the transparency of the films and fluorescence intensity was also investigated. The study carried out led to the elucidation of the necessary conditions for obtaining luminescent film-forming materials with high luminescence intensity and transparency useful for the design of new light concentrators.

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Section: Introductionmentioning

confidence: 99%

Fluorescent Silica Hybrid Film-Forming Materials Based on Salicylaldazine

Rădiţoiu

Raduly

et al. 2020

Coatings

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“…A good number of symmetrical and unsymmetrical azines have largely contributed to the development of coordination chemistry acting as chelating agents having the design of new molecular materials with interesting physical properties [7][8][9][10]. They are known to find applications as nonlinear optical materials (NLO) [11][12]. Among the types of Schiff bases, polyazines are significantly used as nonlinear optical materials (NLO) because of their optical transparency [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Yahyaoui

Bouchama²,

Anak³

et al. 2019

Journal of Molecular Structure

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In this paper, we report the synthesis of new unsymmetrical azines Schiff bases. These compounds were prepared by condensation of hydrazine with different aldehydes and ketones to give (E) -2-hydroxynaphthalene-1-carbaldehyde [(1E) -2-thienylmethylene] hydrazone compound (I) and (Z) -2 -[(E) -1-(2-hydroxyphenyl) ethylidenehydrazin-1-ylidene] -1,2diphenylethanone compound (II). The method adopted consists in reacting the two different carbonyl compounds simultaneously in one step in a stepwise manner reported which is practical and cost-effective. The reaction with a minor modification in operating conditions proceeded efficiently and with excellent performance. The structure of each of the two compounds (I) and (II) was determined by the X-ray diffraction technique performed on single crystals. The asymmetric unity of the two molecules consists of one asymmetry-independent molecule. In addition, hydrogen bonds C-H ... π are observed in the compound (II). We then present a detailed DFT study based on B3LYP / 6-31G (d, p) geometric structures of compounds (I); (II) and another compound (III) also another asymmetric azine (Z) -2 -[(E) -2-benzylidenehydrazine-1-ylidene] -1,2diphenylethanone whose crystal structure is reported. The fundamental vibration wave numbers are calculated and a good agreement between the observed and calculated wave numbers is obtained. The study was extended to the HOMO-LUMO analysis to calculate the energy gap. The calculated HOMO and LUMO energy reveals that the charge is transferred into the molecule.

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“…FTIR spectra are recorded for the pristine 1 and after adding the three trivalent metal ions individually. In the IR spectra, it is noted that the band for the −CN group (azine functional group present in the spacer L) of the pristine MOF 1 at 1627 cm –1 was weakened to a certain extent and also slightly shifted to a lower frequency region when 1 was immersed in an aqueous solution of M 3+ ions (M = Cr 3+ /Al 3+ /Fe 3+ ) and this could be attributed to the interaction between analyte metal ions and the uncoordinated N atom of the azine functionality in the spacer L (Figure S17 in the SI). , Thus, these azine moieties decorating the pores of the framework could be considered as binding sites for specifically interacting with the targeted metal ions (Cr 3+ , Al 3+ , Fe 3+ ) through Lewis acid–base type interactions. Next, the UV–visible absorption spectra of 1 in DMF were measured after adding different metal ions.…”

Section: Resultsmentioning

confidence: 99%

A Highly Selective MOF-Based Probe for Turn-On Luminescent Detection of Al³⁺, Cr³⁺, and Fe³⁺ in Solution and Test Paper Strips through Absorbance Caused Enhancement Mechanism

Mukherjee

Pal

et al. 2022

Inorg. Chem.

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Trivalent metal ions (Cr 3+ , Al 3+ , and Fe 3+ ) constitute a major section of the environmental pollutants, and their excess accumulation has a detrimental effect on health, so their detection in trace quantity has been a hot topic of research. A highly scalable 3D porous Zn-based luminescent metal− organic framework (MOF) has been synthesized by exploiting the mixed ligand synthesis concept. The strategic selection of an aromatic π-conjugated organic linker and N-rich spacer containing the azine functionality as metal ion binding sites immobilized across the pore spaces, have made this MOF an ideal turn-on sensor for Al 3+ , Cr 3+ , and Fe 3+ ions with very high sensitivity, selectivity, and recyclability. An in-depth study revealed absorbance caused enhancement mechanism (ACE) responsible for such turn-on phenomena. In order to make the detection process straightforward, convenient, portable, and economically viable, we have fabricated MOF test paper strips (the MOF could be simply immobilized onto the paper strips) for naked eye visual detection under UV light, which, thus, manifests its potential as a real-time smart sensor for these trivalent ions.

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Fluorescent aromatic symmetrical azines: Synthesis and appraisal of their photophysical and electrochemical properties

Cited by 20 publications

References 30 publications

Fluorescent Silica Hybrid Film-Forming Materials Based on Salicylaldazine

Fluorescent Silica Hybrid Film-Forming Materials Based on Salicylaldazine

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

A Highly Selective MOF-Based Probe for Turn-On Luminescent Detection of Al³⁺, Cr³⁺, and Fe³⁺ in Solution and Test Paper Strips through Absorbance Caused Enhancement Mechanism

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Fluorescent aromatic symmetrical azines: Synthesis and appraisal of their photophysical and electrochemical properties

Cited by 20 publications

References 30 publications

Fluorescent Silica Hybrid Film-Forming Materials Based on Salicylaldazine

Fluorescent Silica Hybrid Film-Forming Materials Based on Salicylaldazine

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

A Highly Selective MOF-Based Probe for Turn-On Luminescent Detection of Al3+, Cr3+, and Fe3+ in Solution and Test Paper Strips through Absorbance Caused Enhancement Mechanism

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A Highly Selective MOF-Based Probe for Turn-On Luminescent Detection of Al³⁺, Cr³⁺, and Fe³⁺ in Solution and Test Paper Strips through Absorbance Caused Enhancement Mechanism