Synthesis of an efficient Pyrene based AIE active functional material for selective sensing of 2,4,6-trinitrophenol

Shyamal, Milan; Maity, Samir; Mazumdar, Prativa; Sahoo, Gobinda Prasad; Maity, Rakesh; Misra, Ajay

doi:10.1016/j.jphotochem.2017.03.030

Cited by 66 publications

(20 citation statements)

References 54 publications

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“…The nitroaromatics (NACs) being the main constituents in explosives, crackers, and rocket fuels, detection of NACs is one of the persuasive challenges in the arena of global security . Above all, the widespread use of explosive formulations poses a serious threat to the human condition, including skin irritation, anemia, and carcinogenicity, among several others . Therefore, the analysis of explosives has been of importance and several attempts have been committed to designing new materials for detecting nitroaromatics (NACs) .…”

Section: Resultsmentioning

confidence: 99%

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

et al. 2020

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Two structurally unique aggregation induced emission (AIE)‐active luminogens have been designed and synthesized based on the furocarbazole skeleton. Such small molecule AIEgens were designed based on forbidden planarity and engineering a twist into the scaffold to realize induction of emission in the aggregated states. The structures were fully characterized and their thermal stabilities, electronic properties, photophysical and electrochemical properties were systematically investigated. The unique twist in the molecules as evident from their X‐ray crystal structure along with the short intermolecular interactions enhances the structural rigidification and restricts detrimental π–π stacking interactions, restricting the internal rotations (RIR) accompanied by a curb of the ICT process, resulting in enhanced emission in the aggregated state. This intriguing luminescent property enabled one of the luminogens to selectively detect trinitrophenol (TNP) over other nitroaromatics in both aqueous and organic media at nanomolar concentrations. Moreover, the good photostabilities and biocompatibilities empowered both luminogens to function as fluorescent bioprobes for cancer cell imaging.

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Section: Resultsmentioning

confidence: 99%

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

et al. 2020

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“…The blocking of single bond rotation and the improved planarity in aggregated states of the molecule (Scheme ) lead to highly emissive with a blue shift in agreement with the AIEE behaviour of the probe (H 2 L). The previous reports showed that the blue shift and the red shift of the spectra of the probe are respectively responsible for H‐type and J‐type aggregation in support of AIEE nature . So considering the observed hypsochromic shift in UV‐Vis spectra of H 2 L, it may be suggested that this AIEE behaviour of the probe is due to the H‐type aggregation.…”

Section: Resultsmentioning

confidence: 99%

Aggregation Induced Emission Enhancement (AIEE) of Naphthalene‐ Appended Organic Moiety: An Al³⁺ Ion Selective Turn‐On Fluorescent Probe

et al. 2020

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An example of an aggregation‐induced emission enhancement (AIEE)‐active new naphthalene appended Schiff base (H2L) as an Al3+ ion selective fluorescent sensor has been successfully designed and synthesized. H2L showed turn‐on fluorescence at high concentration in DMF only, and at low concentration in DMF‐H2O mixtures having high water content (more than 20%). But at very low concentration of H2L and in DMF/H2O solutions with low water fraction (fw ≤ 20%), the fluorescence was turned ON in presence of Al3+ ions, which helps to detect Al3+ ions as low as 4.9×10−7 M with high selectivity in an DMF solution without any interference of other competitive metal ions. The fluorescence of H2L in different conditions and in solid state due to AIE effect has been established with the help of detailed spectroscopic studies, dynamic light scattering (DLS), scanning electron microscope (SEM), life time using time‐resolved photoluminescence and optical fluorescence microscope. The experimentally observed H‐type aggregation nature of the probe H2L has also been supported by the theoretical (DFT studies and TDDFT) studies. This probe (H2L) has also been employed for on‐site Al3+ ions detection in solid state.

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“…When water fraction reaches 90%, a bright yellow emission was observed at 340 nm due to aggregation. AIE might be related to the restriction of intramolecular rotation, the formation of specific aggregates and effects of intramolecular planarization …”

Section: Resultsmentioning

confidence: 99%

Ferrocene‐appended donor–π–acceptor Schiff base: Structural, nonlinear optical, aggregation‐induced emission and density functional theory studies

David

Thirumoorthy

Palanisami

2018

Applied Organom Chemis

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New ferrocenyl Schiff bases [Fc─C(H)═N─C 6 H 3 (OH)(R)] (R = H (1), NO 2 (2)) have been synthesized and characterized using various techniques. Compound 2 was further confirmed using single-crystal X-ray diffraction analysis.Solvatochromism studies of 2 showed redshift from nonpolar to polar solvents. In addition, results of fluorescence studies indicated excellent aggregationinduced emission properties. The quasi-reversible redox wave in electrochemical studies of the Schiff bases evidenced the electron transfer ability of ferrocene to the Schiff base (─C═N─) conjugation group. The second-order nonlinear optical (NLO) properties of 1 and 2 were investigated using the Kurtz-Perry powder technique and 2 showed an effect 1.46 times greater than that of urea reference. Although 2 crystallized in the P2 1 /c centrosymmetric space group, NLO property was observed, due to non-covalent interactions (C─H⋅⋅⋅π). The band gaps were calculated using the diffuse reflectance spectroscopic method and 2 exhibited a low band gap of 2.9 eV which is due to the more electronwithdrawing nature of the nitro group. Quantum chemical calculations were performed on the synthesized compounds using the density functional theory (DFT) and time-dependent DFT approach. The theoretical studies showed that the band gap for the Schiff bases was 3.8 eV (1) and 3.2 eV (2) and they can be considered as candidates for use in optical applications. KEYWORDS aggregation-induced emission (AIE), DFT/TD-DFT, electrochemical studies, ferrocenyl Schiff bases, nonlinear optics | INTRODUCTIONResearch on ferrocene-containing compounds has drawn immense attention due to their wide-ranging applications in the fields of catalysis, [1] sensors, [2] luminescent systems, [3] nonlinear optics [4a] and molecular electronic devices [5] due to their well-established redox switching abilities. [6] Since ferrocene displays a good electrochemical response because of its strong π-donating ability and good reversibility in one-electron oxidation at a desirable

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Synthesis of an efficient Pyrene based AIE active functional material for selective sensing of 2,4,6-trinitrophenol

Cited by 66 publications

References 54 publications

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

Aggregation Induced Emission Enhancement (AIEE) of Naphthalene‐ Appended Organic Moiety: An Al³⁺ Ion Selective Turn‐On Fluorescent Probe

Ferrocene‐appended donor–π–acceptor Schiff base: Structural, nonlinear optical, aggregation‐induced emission and density functional theory studies

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Synthesis of an efficient Pyrene based AIE active functional material for selective sensing of 2,4,6-trinitrophenol

Cited by 66 publications

References 54 publications

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging

Aggregation Induced Emission Enhancement (AIEE) of Naphthalene‐ Appended Organic Moiety: An Al3+ Ion Selective Turn‐On Fluorescent Probe

Ferrocene‐appended donor–π–acceptor Schiff base: Structural, nonlinear optical, aggregation‐induced emission and density functional theory studies

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Aggregation Induced Emission Enhancement (AIEE) of Naphthalene‐ Appended Organic Moiety: An Al³⁺ Ion Selective Turn‐On Fluorescent Probe