AIEE active novel red-emitting D-π-A phenothiazine chalcones displaying large Stokes shift, solvatochromism and “turn-on” reversible mechanofluorochromism

Sachdeva, Tanisha; Milton, Marilyn Daisy

doi:10.1016/j.dyepig.2020.108539

Cited by 33 publications

(15 citation statements)

References 37 publications

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“…They also exhibited AIEE characteristics [24,25]. In addition, chalcone-based AIEE molecules have been reported in several works [26][27][28], which further increases our interest and confidence in the study of the fluorescence characteristics of chalcone compounds. In this project, we tried to acquire smaller molecules through the same ideas and experiences.…”

Section: Introductionmentioning

confidence: 67%

Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Luo

Liu

et al. 2021

IJMS

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Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted increasing interest in recent years. On the basis of our previous research, we successfully designed and synthesized eleven chalcones. Through an optical performance experiment, we confirmed that compounds 1–6 had obvious AIEE properties. As these AIEE molecules had excellent fluorescence properties and a large Stokes shift, we studied their application in living cell imaging, and the results showed that these compounds had low cytotoxicity and good biocompatibility at the experimental concentrations. More importantly, they could specifically label mitochondria. Subsequently, we selected zebrafish as experimental animals to explore the possibilities of these compounds in animal imaging. The fluorescence imaging of zebrafish showed that these AIEE molecules can enter the embryo and can be targeted to aggregate in the digestive tract, which provides a strong foundation for their practical application in the field of biological imaging. Compared with traditional fluorophores, these AIEE molecules have the advantages of possessing a small molecular weight and high flexibility. Therefore, they have excellent application prospects in the field of biological imaging. In addition, the findings of this study have very positive practical significance for the discovery of more AIEE molecules.

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Section: Introductionmentioning

confidence: 67%

Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Luo

Liu

et al. 2021

IJMS

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“…Chalcones have a basic chemistry that provides easier synthesis with a variety of substitutions. Though there are many methods to prepare chalcones, the most commonly adopted process is the Claisen Schmidt condensation in which benzaldehyde and acetophenone derivatives in a liquid solvent reacts with basic or acid catalysts at room temperature or around 50-100 °C (Sachdeva and Milton 2020). A one pot synthetic process with acetophenone and phenylmethanol mixture in the presence of CrO 3 as the oxidizing agent, solid acid catalyst mediated reaction, Sonogashira isomerization coupling reaction, reaction between phenylacetylene and benzaldehyde in the presence of HBr and ionic liquids such as 1-butyl-3-methyl-1H-imidazolium 4-methylbenzenesulfonate (BmimOTs), Suzuki-Miyaura coupling, continuous-flow deuteration and carbonylative Heck coupling reaction (Wu et al 2010a, b;Rueping et al 2011) are the various other methods to synthesize chalcones.…”

Section: Structure and Synthesis Of Chalconesmentioning

confidence: 99%

“…D-π-A architecture based chalcones 3a-d, wherein π-conjugated chalcone unit served as an electron acceptor and phenothiazine moiety acted as an electron donor were synthesized using Claisen-Schmidt condensation reaction (Sachdeva and Milton 2020). The molecular arrangements and photophysical properties of these chalcones were tuned by the introduction of various aryl units having different steric and electronic features substituted onto phenothiazine unit (Fig.…”

Section: Optoelectronic Applications Of Aie-active Chalconesmentioning

confidence: 99%

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Aggregation induced emission of chalcones

Kagatikar

Sunil

2021

Chem. Pap.

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There is always a need for efficient luminescent materials with simple synthesis and possible ease of hydrogen atom or functional group manipulation for use in different optoelectronic and biological applications. However, for certain real-world uses aggregation caused quenching effect of luminophores in their solid/aggregate state is undesirable, and is a cause of concern in areas, wherein the solid-state optical performance is more crucial. In this regard, chalcones have been explored for their ability to display aggregation-induced emission (AIE) or aggregation-induced enhanced emission (AIEE), which can be of practical use. This article is thus focused on an integrated evidence-based report on the AIE/AIEE-active chalcone systems for potential technological and biological applications. Graphic abstract

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“…Phenothiazine is an important heteroatom-containing organic small molecule with unique molecular structure characteristics. The electron-rich atoms, nitrogen and sulfur, endow phenothiazine with stronger electron-donating ability than many other N-heterocycle structures such as carbazole, triphenylamine, and tetrahydroquinoline. − In addition, the nonplanar “butterfly-like” conformation is conducive to the construction of twisted fluorescent molecules, which is extremely beneficial to the luminescence in the condensed state. − This unique conformation gives phenothiazine a great advantage in designing new AIE molecules. − Coupled with the availability of multiple modifiable sites and ease of functionalization, all of these advantages make phenothiazine an excellent candidate for constructing the D–A architecture with excellent optoelectronic properties.…”

Section: Introductionmentioning

confidence: 99%

Phenothiazine-Based Luminophores with AIE, Solvatochromism, and Mechanochromic Characteristics

Huang

Wang

et al. 2021

J. Phys. Chem. B

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Aggregation-induced emission (AIE) fluorescent molecules with unique photoelectric properties have received extensive attention due to the wide range of applications. In this work, two novel phenothiazine-based luminophores DPE-PTZ-Cl and DPE-PTZ-CF 3 were designed based on the frontier molecular orbital (FMO) theory and construction strategy of AIEgens. As expected, both of the luminophores displayed typical AIE behavior and realized the spatial separation of FMOs, which was confirmed by the positive solvatochromism behavior. Their AIE properties could be attributed to the twisted three-dimensional (3D) conformation. Such a conformation resulted from “butterfly-like” phenothiazine and a multirotor structure of diphenylethylene. The spatial separation of FMOs originated from the push–pull electronic synergistic effect of the donor–acceptor (D–A) architecture. Interestingly, DPE-PTZ-Cl also showed a rare blue-shifted mechanochromic (MC) luminescence property. Single-crystal X-ray diffraction (SCXRD) and powder X-ray diffraction (PXRD) experiments were carried out to reveal that the phase transformation between crystalline and amorphous states was responsible for the peculiar solid-state luminescence phenomenon.

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AIEE active novel red-emitting D-π-A phenothiazine chalcones displaying large Stokes shift, solvatochromism and “turn-on” reversible mechanofluorochromism

Cited by 33 publications

References 37 publications

Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Aggregation induced emission of chalcones

Phenothiazine-Based Luminophores with AIE, Solvatochromism, and Mechanochromic Characteristics

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