A new AIE and TICT-active tetraphenylethene-based thiazole compound: Synthesis, structure, photophysical properties and application for water detection in organic solvents

Sun, Hao; Tang, Xinxue; Miao, Bao-Xi; Yang, Yun; Ni, Zhong‐Hai

doi:10.1016/j.snb.2018.04.022

Cited by 95 publications

(27 citation statements)

References 55 publications

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“…Among numerous methods for the detection of water, fluorescence-based sensors show considerable attention due to their simplicity, high sensitivity, convenience, and low cost. To date, a number of fluorescence probes have been developed and applied for water detection such as fluorescent organic molecular probes, metal–organic framework, and Cu nanoclusters. − In recent years, there has been an extended effort in developing CDs as a fluorescent material for the quantitation of water in organic solvents. , Although the bright fluorescent CDs have been used for water detection in these pioneering works, the high sensitivity toward low fractions of water in organic solvents is a significant issue. Furthermore, emission colors of carbon dots noticeable by the naked eye for water detection in organic solvent enhance the advantages of carbon dots.…”

Section: Introductionmentioning

confidence: 99%

Effect of Solvent-Derived Highly Luminescent Multicolor Carbon Dots for White-Light-Emitting Diodes and Water Detection

Kumari

Sahu

2020

Langmuir

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Recently, the multicolor fluorescent carbon dots (CDs) have drawn much attention due to their various applications. Herein, we report multicolor emissive CDs by solvent-controlled and solvent-responded approaches. The blue to red color emissive CDs are obtained by the solvothermal method by varying the solvent during the reaction. The red color emissive CDs (R-CDs) with good quantum yield is obtained in a water medium. The detailed characterization revealed that the solvent controls the particle size, band gap, and nitrogen doping concentration. Specifically, in the protic solvent, the high N content and presence of imine nitrogen are the reason for red emission. However, in an aprotic solvent, the least N doping and a lack of C–O groups are responsible for a blueshift. Interestingly, it was observed that the R-CDs provide a full range of visible color by dispersing in different immiscible solvents. The fluorescence emission in immiscible solvents is redshifted by enhancing the polarity. Moreover, the developed CDs detected the low water concentrations (≤0.2%, v/v) visually and fluorometrically in various organic solvents. Simultaneously, we have employed synthesized CDs in white-light-emitting diodes and fluorescent ink.

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Section: Introductionmentioning

confidence: 99%

Effect of Solvent-Derived Highly Luminescent Multicolor Carbon Dots for White-Light-Emitting Diodes and Water Detection

Kumari

Sahu

2020

Langmuir

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“…In the water fraction range ( f w = 0–60 vol%), the PL intensity was still weak. However, when f w reached 80 vol%, the PL intensity was increased significantly, which was ascribed to the aggregation of the compound ( Figure 4D ) ( Liu et al, 2016 ; Sun et al, 2018 ; Gao et al, 2019 ). Moreover, MOX2 gave a low QY in pure DMSO (0.13%) but a high QY in pure water (2.62%) ( Table 1 ).…”

Section: Resultsmentioning

confidence: 99%

Precise Molecular Design of a Pair of New Regioisomerized Fluorophores With Opposite Fluorescent Properties

Wang

Chen

et al. 2022

Front. Chem.

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Aggregation-induced emission (AIE) has attracted much attention in the past 2 decades. To develop novel AIE-active materials, ACQ-to-AIE transformation via regioisomerization is one of the most straightforward method. However, most of the reported ACQ-to-AIE transformations are achieved by migrating bulky units. In this work, a facile conversion was realized by migrating a small pyrrolidinyl group from para- to ortho-position on the rofecoxib scaffold. As a result, a pair of new isomers named MOX2 and MOX4 exhibited AIE behavior and ACQ activity, respectively. Moreover, MOX2 also showed solvatochromic, mechanochromic, and acidochromic properties with reversible multi-stimulus behavior. Single crystal X-ray analysis of MOX2 revealed that the molecular conformation and its packing mode were responsible for the AIE emission behavior. Further investigation indicated that MOX2 showed high lipid droplets staining selectivity. Taken together, the current work not only provides a new design philosophy for achieving ACQ-to-AIE conversion by migrating a small pyrrolidinyl group but also presents a promising candidate MOX2 for potential applications such as in security ink, optical recording and biological applications.

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“…In general, when the π–π* transition occurs, the excited state has a larger polarity than the ground state, which leads to a greater stabilizing effect of solvent polarity on the excited state. As a consequence, the emission peak of probe DBTC moves toward the long wavelength with the increase of solvent polarity . Moreover, their fluorescence intensities are markedly decreased when the polarity of solvent is increased (Table ), thanks to the sensitivity of the twisted intramolecular charge-transfer (TICT) state to various nonradiative quenching processes …”

Section: Resultsmentioning

confidence: 99%

“…As a consequence, the emission peak of probe DBTC moves toward the long wavelength with the increase of solvent polarity. 40 Moreover, their fluorescence intensities are markedly decreased when the polarity of solvent is increased (Table 1), thanks to the sensitivity of the twisted intramolecular charge-transfer (TICT) state to various nonradiative quenching processes. 41 Aggregation-Induced Emission Enhancement Characteristics of Probe DBTC.…”

Section: ■ Introductionmentioning

confidence: 99%

New Fast, Highly Selective Probe with Both Aggregation-Induced Emission Enhancement and Intramolecular Charge-Transfer Characteristics for Homocysteine Detection

et al. 2019

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A new fluorescence probe 2-(4′-(diphenylamino)-[1,1-biphenyl]-4-yl)-2H-[1,2,3]-triazole-4-carbaldehyde (DBTC) was designed and synthesized through Suzuki coupling reaction between (4-(diphenylamino)phenyl)boronic acid and (4-bromophenyl)-2H-[1,2,3]-triazole-4-carbaldehyde. This probe DBTC had intramolecular charge transfer and aggregation-induced emission enhancement performances and showed high selectivity and sensitivity toward homocysteine (Hcy) in the presence of other amino acids. The detection limit of probe DBTC for Hcy was 3.05 × 10 −6 M, and the mechanism was researched by 1 H NMR titration experiments and mass spectrometry. Furthermore, cell-culture results indicated that probe DBTC was cell permeable and could be used to detect Hcy in living cells. The good characteristics of the probe DBTC had huge application potential use for researching the effects of Hcy in other biological systems.

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A new AIE and TICT-active tetraphenylethene-based thiazole compound: Synthesis, structure, photophysical properties and application for water detection in organic solvents

Cited by 95 publications

References 55 publications

Effect of Solvent-Derived Highly Luminescent Multicolor Carbon Dots for White-Light-Emitting Diodes and Water Detection

Effect of Solvent-Derived Highly Luminescent Multicolor Carbon Dots for White-Light-Emitting Diodes and Water Detection

Precise Molecular Design of a Pair of New Regioisomerized Fluorophores With Opposite Fluorescent Properties

New Fast, Highly Selective Probe with Both Aggregation-Induced Emission Enhancement and Intramolecular Charge-Transfer Characteristics for Homocysteine Detection

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