Imidazole-coumarin containing D – A type fluorescent probe: Synthesis photophysical properties and sensing behavior for F− and CN− anion

Ali, Rashid; Dwivedi, Sushil K.; Mishra, Hirdyesh; Misra, Arvind

doi:10.1016/j.dyepig.2019.108163

Cited by 41 publications

(10 citation statements)

References 45 publications

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“…After isolation of the crude products 3 a-c, the imidazole groups were methylated using NaH and CH 3 I to yield the final products. This methylation is necessary as the presence of the acidic imidazole hydrogen atom can lead to both irreversible electrochemistry [39] and complicated emission behavior due to intra/intermolecular charge transfer. [21,22,40] The identity and purity of all final compounds were verified with 1 H and 13 C{ 1 H} NMR, as well as high resolution mass spectrometry (HRMS).…”

Section: Resultsmentioning

confidence: 99%

Thermally Activated Delayed Fluorescence and Room‐Temperature Phosphorescence in Materials with Imidazo‐pyrazine‐5,6‐dicarbonitrile Acceptors

Hojo

Hudson

2023

Chemistry A European J

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Three donor-acceptor compounds based on the imidazo-pyrazine-5,6-dicarbonitrile (IPDC) acceptor were synthesized. The IPDC emitters exhibit blue to near-infrared (NIR) emission with up to 54 % photoluminescent quantum yield. 9,9-Dimethyl-9,10-dihydroacridine (ACR), phenoxazine (POX), and phenothiazine (PTZ) served as electron donors. IPDC-POX displayed NIR emission in toluene solution, while showing room-temperature phosphorescence in the solid state. IPDC-ACR exhibited yellow thermally activated delayed fluorescence. Interestingly, dual-emissive behavior as well as excitation-dependent thermally activated delayed fluorescence (TADF) was found for IPDC-PTZ, arising from the two conformers of phenothiazine derivatives. Overall, this work describes a novel strong electron acceptor from the fusion of imidazole, pyrazine, and nitrile functional groups into one conjugated heterocycle for materials exhibiting NIR emission, TADF, and/or room-temperature phosphorescence (RTP).

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Section: Resultsmentioning

confidence: 99%

Thermally Activated Delayed Fluorescence and Room‐Temperature Phosphorescence in Materials with Imidazo‐pyrazine‐5,6‐dicarbonitrile Acceptors

Hojo

Hudson

2023

Chemistry A European J

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“…4,[9][10][11][12] However, the stability of conventional organic small molecule uorescent probes for cyanide detection, along with the utilization of toxic volatile organic solvents, imposes constraints on their wider application as practical sensors for cyanide. 13,14 Consequently, the pursuit of stable sensors based on organic and inorganic hybrid materials for the selective detection of CN − ions in aqueous environments remains a challenging and crucial research area.…”

Section: Introductionmentioning

confidence: 99%

Efficient fluorescence-enhanced probe for cyanide ions based on a tetraphenylethene pyridine coordinated copper-iodide complex

Luo¹,

Guo²,

Zheng

et al. 2023

RSC Adv.

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“…To overcome this problem, considerable research efforts have been made to design new receptors that could discriminate both F – and CN – . ,− Aldridge and co-workers utilized a mixture of redox active dyes and metallocene-based organoboranes for the colorimetric discrimination of CN – /F – . In spite of these efforts, a single molecular multifunctional sensor, discriminating F – and CN – , has not been explored much. − Therefore, it is in this context that the authors started thinking that if multiple receptors, varying in their affinities toward F – and CN – , are added in a single molecular entity, these two anions may preferentially bind to the receptor center owing to their difference in polarizabilities.…”

Section: Introductionmentioning

confidence: 99%

Development of a Multifunctional Aggregation-Induced Emission-Active White Light-Emissive Organic Sensor: A Combined Theoretical and Experimental Approach

Chaudhary

Dineshkumar

Roy

2022

ACS Appl. Electron. Mater.

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A far-red to near-infrared (NIR) “aggregation-enhanced emission” (AEE)-active donor–acceptor (D–A)-type probe (denoted as IMZ-CN) is designed and synthesized. The probe IMZ-CN is designed rationally using the quantum mechanical gap tuning (highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energy gap, i.e., ΔE g) approach. The probe is tethered with two different functionalities, i.e., dicyanovinyl (DCV) and benzimidazole (IMZ), which effectively lower the value of ΔE g and cause emission in the far-red to near-infrared region. Furthermore, it selectively detects cyanide (CN–) and fluoride (F–) ions by turn-on emission in pure water without interference between each other. Apart from CN–/F– sensing, the probe (IMZ-CN) is also sensitive toward the acidic environment due to the presence of potential basic nitrogen on the benzimidazole unit. The binding of CN–/F– induces a blue shift in the electronic spectra of IMZ-CN, whereas an acidic environment (e.g., the change in pH from 7 to 2.3) causes red-shifted emission (∼60 nm). Interestingly, IMZ-CN displays a nearly pure white emission during the course of the aggregation-enhanced emission (AEE) mechanism study in the PEG–water binary mixture (99%) with CIE coordinates (0.30, 0.33). The mechanisms behind the emission of white light and the anion-binding/sensing applications (photophysical properties of the probe) are supported by quantum mechanical calculations [using “frontier molecular orbitals” (FMO), “time-dependent density functional theory” (TD-DFT), and “natural transition orbital” (NTO) calculations]. As this multifunctional probe IMZ-CN interacts with CN–, F–, H+, etc., the reactivity parameters [e.g., global chemical hardness (η), global electrophilicity (ω), etc.] were calculated by applying the concept of “density functional reactivity theory” (DFRT) to validate its reactivity.

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Imidazole-coumarin containing D – A type fluorescent probe: Synthesis photophysical properties and sensing behavior for F− and CN− anion

Cited by 41 publications

References 45 publications

Thermally Activated Delayed Fluorescence and Room‐Temperature Phosphorescence in Materials with Imidazo‐pyrazine‐5,6‐dicarbonitrile Acceptors

Thermally Activated Delayed Fluorescence and Room‐Temperature Phosphorescence in Materials with Imidazo‐pyrazine‐5,6‐dicarbonitrile Acceptors

Efficient fluorescence-enhanced probe for cyanide ions based on a tetraphenylethene pyridine coordinated copper-iodide complex

Development of a Multifunctional Aggregation-Induced Emission-Active White Light-Emissive Organic Sensor: A Combined Theoretical and Experimental Approach

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