Tetraphenylethylene-based color-tunable AIE-ESIPT chromophores

Hu, Zhen; Zhang, Haoke; Chen, Yan; Wang, Qingsong; Elsegood, Mark R. J.; Teat, Simon J.; Feng, Xing; Islam, Md. Monarul; Wu, Fugen; Tang, Ben Zhong

doi:10.1016/j.dyepig.2019.108175

Cited by 31 publications

(18 citation statements)

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“…As the 2,6-dihydroxynaphthalene-1,5-dialdehyde reacts with aniline to form the -CH=N bond, this functional group bridges the naphthalene and benzene ring leading to the probes conjugated structure. When probe molecules are excited by light, an electron flow from the naphthalene ring to the imine group can easily occur; on the other hand, in the THF/H 2 O solution, there exist a fast structure convert from enol form to keto form in the molecule [ 32 ], the intramolecular hydrogen bonds limit the nonradiative transition; thus, the probe L in the dissolved state emits orange light [ 33 , 34 , 35 ]. According to the 1 H-NMR spectroscopic titration experiments, the probe coordinates with Cu 2+ via the N atom of imine and the O atom of -OH to form a stable complex.…”

Section: Resultsmentioning

confidence: 99%

A Simple Turn-off Schiff Base Fluorescent Sensor for Copper (II) Ion and Its Application in Water Analysis

et al. 2021

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An aniline-functionalized naphthalene dialdehyde Schiff base fluorescent probe L with aggregation-induced enhanced emission (AIEE) characteristics was synthesized via a simple one-step condensation reaction and exhibited excellent sensitivity and selectivity towards copper(II) ions in aqueous media with a fluorescence “ turn-off ” phenomenon. The detection limit of the probe is 1.64 × 10−8 mol·L−1. Furthermore, according to the results of the UV-vis/fluorescence titrations, Job’s plot method and 1H-NMR titrations, a 1:2 stoichiometry was identified. The binding constant between L and Cu2+ was calculated to be Ka = 1.222 × 103. In addition, the AIEE fluorescent probe L could be applied to detection in real water samples with satisfactory recoveries in the range 99.10–102.90% in lake water and 98.49–102.37% in tap water.

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Section: Resultsmentioning

confidence: 99%

A Simple Turn-off Schiff Base Fluorescent Sensor for Copper (II) Ion and Its Application in Water Analysis

et al. 2021

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“…The design and development of organic nanoprobes without any synthetic complications for various bio- and environmental-related applications are still regarded as tough tasks. − In regard to the π–π stacking and self-assembly, many organic nanoprobes were reported for the sensory and AIEE studies with exceptional biological applications. − However, a limited number of those nanoprobes possessed the p- or n-type semiconducting property so that it can be adapted in the organic thin-film transistor (OTFT)-based sensory interrogations. , Moreover, on the one hand, the synthesis of such nanoprobes involved multiple synthetic steps and required a careful optimization. − On the other hand, Schiff base derivatives synthesized by a one-pot reaction with great yield were reported for sensory studies in both solution and OTFT studies. − For the OTFT-based detection of analytes in aqueous media, the fabricated materials and devices must possess the following characteristics: (i) the probes cannot be soluble in water; (ii) the probes must have either p- or n-type semiconducting properties; (iii) the probes must display a certain selectivity to specific analytes; and (iv) the resulting OTFT devices must be stable in an aqua environment . A probe with the AIEE property is considered as a suitable one because of its water stability and insolubility.…”

Section: Introductionmentioning

confidence: 99%

Pyrene-Based AIEE Active Nanoprobe for Zn²⁺ and Tyrosine Detection Demonstrated by DFT, Bioimaging, and Organic Thin-Film Transistor

Shellaiah

Chen

Thirumalaivasan

et al. 2021

ACS Appl. Mater. Interfaces

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The development of aggregation-induced emission enhancement (AIEE) active nanoprobes without any synthetic complication for solution-state and organic thin-film transistor (OTFT)-based sensory applications is still a challenging task. In this study, the novel pyrene-incorporated Schiff base (5-phenyl-4-((pyren-1-ylmethylene)amino)-4H-1,2,4-triazole-3-thiol; PT2) with an AIEE property was synthesized via a one-pot reaction and was reported for detecting Zn 2+ and tyrosine in the solution state and OTFT. In the AIEE studies of PT2 (in CH 3 CN) at various water fractions (f w : 0− 97.5%), the existence of J-aggregation, crystalline changes, and nanofibers formation was confirmed by ultraviolet absorption/photoluminescence (UV/PL) spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM), and dynamiclight scattering (DLS) techniques. Similarly, PT2-based Zn 2+ detection and sensory reversibility with tyrosine were demonstrated by UV/PL studies with evidence related to crystalline/nanolevel changes in PXRD, SEM, TEM, AFM, and DLS data. Distinct decay profiles associated with the AIEE and sensory responses of PT2 were observed in time-resolved photoluminescence spectra. From the standard deviation and linear fittings of PL titrations, detection limits (LODs) of the Zn 2+ with PT2 and the tyrosine with PT2-Zn 2+ were estimated as 0.79 and 45 nM, respectively. High-resolution mass and 1 H NMR results confirmed 2:1 and 1:1 stoichiometry and binding sites of PT2-Zn 2+ -PT2* and tyrosine-Zn 2+ complexes. Moreover, the values of association constants determined by linear fittings were 4.205 × 10 −7 and 1.73 × 10 −8 M −2 , correspondingly. Optimization via the density functional theory disclosed the binding sites and suppression of twisted intramolecular charge transfer/photoinduced electron transfer (TICT/ PET) as well as the involvement of restricted intramolecular rotation in the AIEE and PET "ON-OFF-ON" mechanisms in the Zn 2+ and tyrosine sensors. Results from the B16−F10 cellular and zebrafish imaging of AIEE, Zn 2+ , and tyrosine sensors further attested the applicability of PT2 in biological samples. Finally, the PT2 and pentacene-incorporated OTFT devices were fabricated. The devices displayed more than 90% change in drain-source current when reacted with Zn 2+ with an LOD of 5.46 μM but showed no response to tyrosine, thereby confirming the reversibility. Moreover, the OTFT devices also demonstrated Zn 2+ ion detection in tap water and lake water samples.

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“…However, some new luminescent materials have an opposite effect, demonstrating bright-light emission upon aggregation in the film state. Typically, tetraphenylethylene (TPE) derivatives have a propeller-shaped structure that is a representative chemical structure exhibiting AIE characteristics [21][22][23][24][25][26][27]. Therefore, in the present study, we focus on new additives for perovskite-based lightemitting material components by using TPE and Br-substituted TPE derivatives to improve the PL light-emitting performance of film-state perovskites.…”

Section: Introductionmentioning

confidence: 99%

Three-Color White Photoluminescence Emission Using Perovskite Nanoplatelets and Organic Emitter

et al. 2022

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Three organic blue-light-emitting tetraphenylethylene (TPE) derivatives that exhibit aggregation-induced emission (AIE) were used as additives in the preparation of inorganic perovskite-structured green-light-emitting materials for three-color white-light emission. For these organic–inorganic light-emitting materials, two-color (blue and green) light-emitting films based on the CsPbBr3 perovskite-structured green-light-emitting inorganic material were prepared. The three TPE derivatives were prepared by varying the number of bromide groups, and a distinct AIE effect was confirmed when the derivatives were dissolved in a water–tetrahydrofuran mixed solvent containing 90 vol% water. When 0.2 molar ratio of the 1,1,2,2-tetrakis(4-bromophenyl)ethylene (TeBrTPE) additive was mixed with nanocrystal-pinning toluene solvent, the green-light-emission photoluminescence quantum efficiency (PLQY) value at 535 nm was 47 times greater than that of the pure bulk CsPbBr3 without additives and a blue emission at 475 nm was observed from the TeBrTPE itself. When a CBP:Ir(piq)3 film was prepared on top of this layer, three PL peaks with maximum wavelength values of 470, 535, and 613 nm were confirmed. The film exhibited white-light emission with CIE color coordinates of (0.25, 0.36).

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Tetraphenylethylene-based color-tunable AIE-ESIPT chromophores

Cited by 31 publications

References 50 publications

A Simple Turn-off Schiff Base Fluorescent Sensor for Copper (II) Ion and Its Application in Water Analysis

A Simple Turn-off Schiff Base Fluorescent Sensor for Copper (II) Ion and Its Application in Water Analysis

Pyrene-Based AIEE Active Nanoprobe for Zn²⁺ and Tyrosine Detection Demonstrated by DFT, Bioimaging, and Organic Thin-Film Transistor

Three-Color White Photoluminescence Emission Using Perovskite Nanoplatelets and Organic Emitter

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Tetraphenylethylene-based color-tunable AIE-ESIPT chromophores

Cited by 31 publications

References 50 publications

A Simple Turn-off Schiff Base Fluorescent Sensor for Copper (II) Ion and Its Application in Water Analysis

A Simple Turn-off Schiff Base Fluorescent Sensor for Copper (II) Ion and Its Application in Water Analysis

Pyrene-Based AIEE Active Nanoprobe for Zn2+ and Tyrosine Detection Demonstrated by DFT, Bioimaging, and Organic Thin-Film Transistor

Three-Color White Photoluminescence Emission Using Perovskite Nanoplatelets and Organic Emitter

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Pyrene-Based AIEE Active Nanoprobe for Zn²⁺ and Tyrosine Detection Demonstrated by DFT, Bioimaging, and Organic Thin-Film Transistor