Fluorescent imidazole-based chemosensors for the reversible detection of cyanide and mercury ions

Emandi, Ganapathi; Flanagan, Keith J.

doi:10.1039/c8pp00226f

Cited by 37 publications

(15 citation statements)

References 74 publications

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“…Therefore, it is necessary to adopt a simple emitter architecture and an appropriate design of the EML layout, which involves the careful setting of the exciton formation position and ensuring the exciton confinement and considering the diffusion or migration of high-energy triplet excitons to adjacent layers. [9] Imidazole derivatives are proven to be promising materials with nonlinear optical, [10] fluorescent, [11] phosphorescent, [12] luminescent, and photochromic properties and are found to be suitable for the photonics, sensing, and optical switches, etc. [13] Our previous work proposed a series of imidazole-based host molecules, which confirmed an extremely balanced carrier mobility strategy to produce maximum brightness and external quantum efficiency (EQE max ) (2.80 × 10 5 cd m À 2 and 40.6 %) to achieve extraordinary tandem OLEDs.…”

Section: Introductionmentioning

confidence: 99%

Dicyano‐Imidazole: A Facile Generation of Pure Blue TADF Materials for OLEDs

Liu

Luo

et al. 2021

Chemistry A European J

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A series of dicyano-imidazole-based molecules with thermally activated delayed fluorescence (TADF) properties were synthesized to obtain pure blue-emitting organic lightemitting diodes (OLEDs). The targeted molecules used dicyano-imidazole with a short-conjugated system as the electron acceptor to strong intermolecular π-π interactions, and provide a relatively shallow energy level of the lowest unoccupied molecular orbital (LUMO). The cyano group was selected to improve imidazole as an electron acceptor due to its prominent electron-transporting characteristics. Four different electron donors, that is, 9,9-dimethyl-9,10-dihydroacridine (DMAC), 10H-spiro(acridine-9,9'-fluoren) (SPAC), and 9,9diphenyl-9,10-dihydroacridine (DPAC), were used to alternate the highest occupied molecular orbital (HOMO) energy level to tune the emission color further. The crowded molecular structure in space makes the electron donor and acceptor almost orthogonal, reducing the energy gap (ΔE ST ) between the first excited singlet (S 1 ) and the triplet (T 1 ) states and introducing significant TADF property. The efficiencies of the blue-emissive devices with imM-SPAC and imM-DMAC obtained in this work are the highest among the reported imidazole-based TADF-OLEDs, which are 13.8 % and 13.4 %, respectively. Both of Commission Internationale de l'Eclairage (CIE) coordinates are close to the saturated blue region at (0.17, 0.18) and (0.16, 0.19), respectively. Combining these tailor-made TADF compounds with specific device architectures, electroluminescent (EL) emission from sky-blue to deep-blue could be achieved, proving their great potential in EL applications.

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Section: Introductionmentioning

confidence: 99%

Dicyano‐Imidazole: A Facile Generation of Pure Blue TADF Materials for OLEDs

Liu

Luo

et al. 2021

Chemistry A European J

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“…Imidazole ring is an essential heterocyclic compound containing two nitrogens in its structure. In literature studies, it is seen that imidazole compounds are used in various fields such as biomimetic catalysts [1][2][3] , medical drugs 4 , artificial receptors 5 , agricultural chemicals 6 , sensors 7 , supramolecular ligands 8 , and batteries 9 . The imidazole ring contains an acidic proton as well as a nitrogen atom with a basic character.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of imidazo-1,4-oxazinone derivatives and investigation of reaction mechanism

Taşdemir

2021

Turk J Chem

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In this study, nine different C-2 aroyl imidazole derivatives were synthesized in a one pot reaction with two steps, and the reduction reactions of these derivatives with NaBH4 were carried out under mild conditions. Substitution reaction of obtained imidazo methanol derivatives with chloroacetylchloride reagent and ring reaction of substitution products were investigated. It was determined that 1,4-imidazoxazinone derivative was obtained as a result of the cyclization reaction. The intermediate products obtained during the cyclization reaction were isolated, and the path of the reaction under different conditions was discussed.

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“…Recently, imidazole compounds have attracted extensive attention due to their fascinating optical properties . The imidazole nucleus is a key building block that has been extensively used in anion sensors, ionic liquids, as well as electronic and optical materials . Triphenylimidazoles played an important role in the discovery of chemiluminescence, for this purpose tetraarylimidazoles have recently attracted significant interest .…”

Section: Introductionmentioning

confidence: 99%

“…[26][27][28][29][30][31][32] The imidazole nucleus is a key building block that has been extensively used in anion sensors, ionic liquids, as well as electronic and optical materials. [33][34][35][36][37] Triphenylimidazoles played an important role in the discovery of chemiluminescence, for this purpose tetraarylimidazoles have recently attracted significant interest. [38][39][40] Nevertheless, the effects of substituent groups on the imidazole ring on the photochromic properties are not clear.…”

Section: Introductionmentioning

confidence: 99%

Photochromic Properties of Novel One‐pot Multicomponent Synthesized Tetraarylimidazoles

et al. 2019

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Acetic acid mediated synthesis of novel tetraarylimidazoles derivatives has been reported via multicomponent reaction of benzil or phenanthrene‐9,10‐dione, NH4OAc, vanillin and aniline derivatives under microwave irradiation. Several novel tetraarylimidazole derivatives, phenanthroimidazole and bis‐tetraphenylimidazole bearing a 2‐methoxyphenol substituent at position 2 of imidazole ring were prepared. The advantages of this method are the one‐pot preparation of compounds, in short reaction times (4‐7 min) and good yields. All synthesized compounds with a 2‐methoxyphenol substituent at position 2 of imidazole ring exhibited good photochromic behavior. The photoisomerization can be performed from ground state to triplet excited state according to TD‐DFT calculation. The results showed that the presence of ortho‐methoxy substituent to hydroxyl substitution has the greatest effect on photochromic properties of target compounds. Furthermore, a pattern was successfully visualized upon UV light irradiation, which suggested that these compounds can be served as a security ink or an anti‐counterfeiting mark for photo printing.

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Fluorescent imidazole-based chemosensors for the reversible detection of cyanide and mercury ions

Abstract: Imidazole-based conjugate acts as a reversible sensor towards CN− and Hg2+ in CH3CN–H2O.

Cited by 37 publications

References 74 publications

Dicyano‐Imidazole: A Facile Generation of Pure Blue TADF Materials for OLEDs

Dicyano‐Imidazole: A Facile Generation of Pure Blue TADF Materials for OLEDs

Synthesis of imidazo-1,4-oxazinone derivatives and investigation of reaction mechanism

Photochromic Properties of Novel One‐pot Multicomponent Synthesized Tetraarylimidazoles

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