Two novel AIEE-active imidazole/ α-cyanostilbene derivatives: photophysical properties, reversible fluorescence switching, and detection of explosives

Zhang, Yuyang; Huang, Jianyan; Kong, Lin; Tian, Yupeng; Yang, Jiaxiang

doi:10.1039/c7ce01842h

Cited by 35 publications

(15 citation statements)

References 65 publications

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“…Cyanostilbene (CS) type chromophores are promising candidates for the development of new organic functional materials because of their prominent optoelectronic properties. 14,15 Recently, these compounds have been employed to fabricate various fascinating CT supramolecular assemblies with tunable emission compared to the individual D/A compounds. 16−21 Due to the ease of functionalization of αcyanostilbene at the terminal position and the hydrogen bond interaction ability of cyano group, it offers a facile way to synthesize two component molecular aggregates.…”

Section: ■ Introductionmentioning

confidence: 99%

Investigation of Charge-Transfer Interaction in Mixed Stack Donor–Acceptor Cocrystals Toward Tunable Solid-State Emission Characteristics

Usman¹,

Khan

Wang³

et al. 2018

Crystal Growth & Design

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The formation of three mixed binary charge transfer (CT) cocrystals with tunable photoluminescence behavior featuring both CT interaction and directional hydrogen bonding is presented. Our strategy consists of the CT induced cocrystallization of three polycyclic (naphthalene, anthracene, and pyrene) carrying α-cyanostilbene (CS) derivatives, namely, 3-(naphthalene-2-yl)-2-(p-tolyl) acrylonitrile (NPA), 3-(anthracene-9-yl)-2-phenylacrylonitrile (APA), and 2-(4-methoxyphenyl)-3-(pyrene-1-yl) acrylonitrile (MPA) as donors (D) with 1,2,4,5-tetracyanobenzene (TCNB) as an acceptor (A). The as-prepared cocrystals were probed in detail by various analytical techniques, namely, X-ray diffraction data, vibrational spectroscopy, diffuse reflectance absorption spectroscopy, fluorescence properties, and fluorescence quantum yields and lifetimes, affirming the formation of CT complexes. Complex IA features a mixed stack arrangement (D–A–D–A–D), while IIA and IIIA revealed (DAD---DAD) stack arrangement. The CT products showed distinct tunable emission colors and photoluminescence characteristics, which is closely associated with the CT interactions between the donor and acceptor moiety, and ionization potential or the π-electron rich character of the polycyclic moiety of the donor molecule. This research demonstrates the development of new hybrid CT functional materials with enhanced optical properties such as absorption, fluorescence emissions, and lifetimes compared to the pristine donors, which is important for the exploration of new solid-state luminescent materials.

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Section: ■ Introductionmentioning

confidence: 99%

Investigation of Charge-Transfer Interaction in Mixed Stack Donor–Acceptor Cocrystals Toward Tunable Solid-State Emission Characteristics

Usman¹,

Khan

Wang³

et al. 2018

Crystal Growth & Design

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“…However, efforts are still underway to develop effective conjugated polymer based theranostic agents for controllable cancer detection and diagnosis. Applications of aggregationinduced emission (AIE) of luminogens such as cyanosubstituted diarylethene derivatives, 18,19 tetraphenylethene (TPE) derivatives, 20,21 distyrylanthracene derivatives, 22,23 a-cyanostilbene derivatives 24,25 in chemosensors and bio-imaging are well-documented. 26 Polymerization-induced self-assembly (PISA) has also been investigated to prepare positive contrast agents for magnetic resonance imaging (MRI).…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted facile synthesis of poly(luminol-co-phenylenediamine) copolymers and their potential application in biomedical imaging

et al. 2018

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“…Picric acid (PA) is a harmful pollutant for the environment and also toxic to human health. , Moreover, trace detection of PA is also very important in combating terrorism, maintaining national security, and environmental safety . TPA derivatives are the favorite choices to develop chemosensors for PA detection, which can offer more diffusion channels for the exciton to migrate. , Our preliminary experiments demonstrate that TPAs-3(NC–Ph–OH) is very effective for detecting PA in a contact mode. For instance, in a DMSO solution, the fluorescence titration for TPAs-3(NC–Ph–OH) with PA reveals that the emission intensity rapidly died upon the addition of increasing amounts of the PA solution, and the quenching efficiency is found to be 93% when PA is loaded as 52 μM.…”

Section: Resultsmentioning

confidence: 87%

Supramolecular Polymerizations via AIE-Active Monomers: Synthesis, Self-Assembly Mechanism Study, and Explosive Detection

Yin

Zhang

Yang

et al. 2020

Ind. Eng. Chem. Res.

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The small molecule-based supramolecular gels are a novel type of soft material and have attracted extensive research attention in the past decades, wherein the most challenging work is to look for a small molecule used as a monomer to construct uniform assemblies via multiple intermolecular interactions. Obviously, if the monomer is of a rigid or an aromatic framework and also has the ability to form supramolecular gels, the resulting polymers will have the potential to be used as optical materials, such as sensors. In this paper, TPAs-3(NC−Ph−OH) is synthesized, which is very seldomly seen being used as a monomer in supramolecular systems and is a Schiff base framework synthesized from o-hydroxybenzaldehyde and aromatic amines. Additionally, TPAs-3(NC−Ph−OH) is a typical aggregationinduced emission (AIE) luminogen (AIEgen). This property endows the corresponding supramolecular polymers with more interesting optical behaviors, such as different fluorescence performances in the different states (gel and sol) and under the external stimulus (with or without external pressures). Then, we postulate the TPAs-3(NC−Ph−OH) self-assembly mechanism from different points, including single-crystal diffraction analysis, matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry, infrared (IR) spectroscopy, UV spectrum, and scanning electron microscopy (SEM) analysis. Finally, TPAs-3(NC−Ph−OH) is employed as a fluorescence sensor for the detection of explosive compound picric acid (PA), which demonstrates excellent sensitivity and selectivity for PA analysis qualitatively and quantitatively. Especially, a new way of fingerprint analysis is accomplished by TPAs-3(NC−Ph−OH) and the PA system due to the perfect on−off sensing performance.

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Two novel AIEE-active imidazole/ α-cyanostilbene derivatives: photophysical properties, reversible fluorescence switching, and detection of explosives

Abstract: Novel imidazole derivatives containing the α-cyanostilbene unit can act as reversible acid/base stimulated fluorescence switches in the solid state, as chemosensors for explosives detection in aqueous systems, and as test strip detectors.

Cited by 35 publications

References 65 publications

Investigation of Charge-Transfer Interaction in Mixed Stack Donor–Acceptor Cocrystals Toward Tunable Solid-State Emission Characteristics

Investigation of Charge-Transfer Interaction in Mixed Stack Donor–Acceptor Cocrystals Toward Tunable Solid-State Emission Characteristics

Microwave-assisted facile synthesis of poly(luminol-co-phenylenediamine) copolymers and their potential application in biomedical imaging

Supramolecular Polymerizations via AIE-Active Monomers: Synthesis, Self-Assembly Mechanism Study, and Explosive Detection

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