135. Polyphenylethylenes. Part I. Preparation and characteristics of tetra-p-nitrophenylethylene

Gorvin, John H.

doi:10.1039/jr9590000678

Cited by 20 publications

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“…The chemosensor ( 4 ) was synthesized in three steps starting from tetraphenylethylene 1 (Figure ). In the first step, the nitration of tetraphenylethylene yielded the tetranitro‐ derivative 2 in 90% yield which on reduction gave the tetraamino‐ derivative 3 in 73% yield . The condensation of 4,4’,4’’,4’’’‐(ethene‐1,1,2,2‐tetrayl)tetraaniline ( 3 ) with salicylaldehyde in the presence of catalytic amount of glacial acetic acid in ethanol yielded the chemosensor 4 in 48% yield.…”

Section: Resultsmentioning

confidence: 99%

“…In the first step, the nitration of tetraphenylethylene yielded the tetranitro-derivative 2 in 90% yield which on reduction gave the tetraamino-derivative 3 in 73% yield. [39] The condensation of 4,4',4'',4'''-(ethene-1,1,2,2-tetrayl)tetraaniline (3) with salicylaldehyde in the presence of catalytic amount of glacial acetic acid in ethanol yielded the chemosensor 4 in 48% yield. All the molecules were characterized by NMR and mass spectroscopy (Figure S1-S3) and the structure of 4 was also confirmed through single crystal X-ray crystallography (Figure 2 Table S1-S3, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

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Selective Metal‐Ion Detection and Activatable Photosensitization Properties of a Tetraphenylethylene‐Based Salicylideneimine

et al. 2019

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Development of chemosensors for metal ions is an active area of research. Fluorescent chemosensors capable of detecting multiple metal ions are valuable because of their potential utility in diagnostics and environmental science. We have synthesized a Schiff‐base chemosensor based on the tetraphenylethylene chromophore. It was observed that the chemosensor interacts with Cu(II) and Zn(II) in acetonitrile with high association constants of 2.33 × 1021 and 1.33 × 1021 M−4, respectively. Moreover, the interaction of these metal ions with the chemosensor resulted in visual colour and fluorescence changes. Nanoaggregates of this molecule, on the other hand, were observed to be selective towards Cu(II) in the aqueous medium. It is also noteworthy that the binding of Cu(II) activates photosensitization property of this molecule and generates singlet oxygen efficiently.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Selective Metal‐Ion Detection and Activatable Photosensitization Properties of a Tetraphenylethylene‐Based Salicylideneimine

et al. 2019

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“…42 The TPE-F compound was prepared by facile reaction of TPE-AM with 1-isocyanato-3,5-bis(trifluoromethyl)benzene (Scheme 1). The compounds were confirmed using nuclear magnetic resonance (NMR) and mass spectrometry (MS), and given in the Supporting Information Figure S1-S4.…”

Section: Scheme 1 Reaction Procedures For Preparation Of Tpe-fmentioning

confidence: 99%

Ultrasmall Organic Nanoparticles with Aggregation-Induced Emission and Enhanced Quantum Yield for Fluorescence Cell Imaging

Bai

et al. 2016

Anal. Chem.

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The use of fluorescence probes for biomedical imaging has attracted significant attention over recent years owing to their high resolution at cellular level. The probes are available in many formats including small particle size based imaging agents which are considered to be promising candidates, due to their excellent stabilities. Yet, concerns over the potential cytotoxicity effects of inorganic luminescent particles have led to questions about their suitability for imaging applications. Exploration of alternatives inspired us to use organic fluorophores with aggregation-induced emission (AIE), prepared by functionalizing the amine group on tetraphenylethene with 3,5-bis(trifluoromethyl)phenyl isocyanate. The as-synthesized novel AIE fluorophore (TPE-F) display enhanced quantum yield and longer lifetime as compared with its counterparts (4,4',4″,4‴-(ethene-1,1,2,2-tetrayl)tetraaniline, TPE-AM). Furthermore, the TPE-F was encapsulated into small-size organic nanoparticles (NPs; dynamic light scattering size, ∼10 nm) with polysuccinimide (PSI). The biocompatibility, excellent stability, bright fluorescence, and selective cell targeting of these NPs enable the as-prepared TPE-F NPs to be suitable for specific fluorescence cell imaging.

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“…Small molecular compounds including tetra-p-aminophenylethylen (TPE-NH 2 ) and propargyl 2-bromo-2-methylpropionamide (BMP) were prepared according to the previously reported procedures. [48,50] The synthetic routes of other intermediate compounds and polymers (Pn) were shown in Scheme 3.…”

Section: Synthesis Of Small Intermediate Molecules and Polymermentioning

confidence: 99%

“…[48,50] The synthetic routes of other intermediate compounds and polymers (Pn) were shown in Scheme 3.…”

Section: Synthesis Of Small Intermediate Molecules and Polymermentioning

confidence: 99%

Organic Nanoprobes for Fluorescence and ¹⁹F Magnetic Resonance Dual‐Modality Imaging

Guo

et al. 2017

Chin. J. Chem.

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135. Polyphenylethylenes. Part I. Preparation and characteristics of tetra-p-nitrophenylethylene

Cited by 20 publications

References 0 publications

Selective Metal‐Ion Detection and Activatable Photosensitization Properties of a Tetraphenylethylene‐Based Salicylideneimine

Selective Metal‐Ion Detection and Activatable Photosensitization Properties of a Tetraphenylethylene‐Based Salicylideneimine

Ultrasmall Organic Nanoparticles with Aggregation-Induced Emission and Enhanced Quantum Yield for Fluorescence Cell Imaging

Organic Nanoprobes for Fluorescence and ¹⁹F Magnetic Resonance Dual‐Modality Imaging

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135. Polyphenylethylenes. Part I. Preparation and characteristics of tetra-p-nitrophenylethylene

Cited by 20 publications

References 0 publications

Selective Metal‐Ion Detection and Activatable Photosensitization Properties of a Tetraphenylethylene‐Based Salicylideneimine

Selective Metal‐Ion Detection and Activatable Photosensitization Properties of a Tetraphenylethylene‐Based Salicylideneimine

Ultrasmall Organic Nanoparticles with Aggregation-Induced Emission and Enhanced Quantum Yield for Fluorescence Cell Imaging

Organic Nanoprobes for Fluorescence and 19F Magnetic Resonance Dual‐Modality Imaging

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Organic Nanoprobes for Fluorescence and ¹⁹F Magnetic Resonance Dual‐Modality Imaging