Tritylisation of pyrene, perylene and coronene: a new family of switchable fluorescent labels

Shchepinov, Mikhail S.; Korshun, Vladimir A.; Egeland, Ryan D.; Southern, Edwin M.

doi:10.1016/s0040-4039(00)00737-1

Cited by 13 publications

(6 citation statements)

References 19 publications

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“…Coronene has been demonstrated to act as bioprobes, [192] useful in biological studies, [193] including DNA cleavage and others [194–195] . In one such precedent, fluorescent on/off labels based on coronene were used for multicolour DNA detection [196–197] . In addition, ratiometric fluorescent probes, relying on coronene, were able to detect microenvironment changes and micelle formation [198] .…”

Section: Resultsmentioning

confidence: 99%

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Kumar

Tao

2021

Chemistry An Asian Journal

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In recent years, a variety of new designs of coronene‐based polycyclic aromatic hydrocarbons (PAHs) with diverse functions have emerged to serve as complementary materials in organic chemistry and materials chemistry. In the present review, we highlight the modern aspects of syntheses related to or different from the strategies used in the early era of coronene research. Systematic extension and expansion of coronene backbones to wide categories of angular PAHs are covered. The substitution and extension of coronene architectures, by incorporating functional groups and by fusing small and large conjugated units, advatangeously enrich their photophysical, electrochemical, self‐assembling, and other properties, of which are discussed to demostrate their impact in materials chemistry. While the highly symmetric coronenes, tribenzocoronenes and hexabenzocoronenes conceived wide potential in charge‐transporting, electroluminescent, sensing, and other applications, other related derivatives such as dibenzo, tetrabenzo and pentabenzocoronenes also displayed their potentials as exemplified by their use as charge‐conduction channel in transistor application.

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Section: Resultsmentioning

confidence: 99%

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Kumar

Tao

2021

Chemistry An Asian Journal

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“…fluorescence resonance energy transfer (FRET). The fluorescent spectrum of the model compound 45 29 in dichloromethane shows only perylene fluorescence upon pyrene excitation, confirming an efficient energy transfer from pyrene to perylene (whereas 1+1 mixture of model butylamides 42 and 43 shows superposition of the pyrene and perylene fluorescence).…”

Section: Modified Trityls: Colour and Fluorescencementioning

confidence: 81%

“…Indeed, compounds 42-45 containing highly absorptive residues of polycyclic aromatic hydrocarbons gave distinct [M 2 OH] + peaks in LDI mass spectra on ionisation with 340 nm laser. 29 Interestingly, the [M 2 2OH] + (and not the expected [M 2 2OH] 2+ ) peak was detected for compound 45, thus suggesting possible formation of a monocation-monoradical from 45.…”

Section: Other Mass-spec Applicationsmentioning

confidence: 92%

Recent applications of bifunctional trityl groups

Shchepinov¹,

Korshun

2003

Chem. Soc. Rev.

219

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Triphenylmethyl derivatives represent an important class of dyestuffs as well as a useful family of protecting groups widely used in organic synthesis to transiently block various functional moieties. These applications are well documented and have been a subject of a number of reviews. Here we focus instead on some novel applications of a trityl which make good use of its ability to easily form a stabilised cation in combination with additional peripheral functionalities. Topics covered include applications in bioconjugation, cross-linking, mass-spectrometry, fluorescence and optics.

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“…The Friedel-Cras acylation reaction is an electrophilic aromatic substitution reaction, oen undertaken in a chlorinated hydrocarbon solvent, such as DCM. [55][56][57] The commercially important, Lewis acid catalysed (FeCl 3 ) synthesis of 4-methoxyacetophenone (1) from anisole and acetic anhydride was used to assess the suitability of MO for the substitution of traditional organic solvents (Scheme 2).…”

Section: Friedel-cras Acylationmentioning

confidence: 99%

3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents

et al. 2021

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Tritylisation of pyrene, perylene and coronene: a new family of switchable fluorescent labels

Cited by 13 publications

References 19 publications

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Recent applications of bifunctional trityl groups

3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents

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