Synthesis and properties of perylene pigments

Nagao, Yuki

doi:10.1016/s0300-9440(97)00017-9

Cited by 81 publications

(39 citation statements)

References 25 publications

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“…[9] As the solubility of nitroxide 2 was extremely poor in the majority of organic solvents, it was decided to focuso nt he preparation of unsymmetrical perylened iimides which would incorporate both anitroxide unit and asolubilisingg roup tethered through the covalent imide bonds onto the perylene unit similart ot he approach employed by Nagao. [20] Initial attempts to generate am ononitroxide-containingp erylene diimide involved the stepwise addition of 2,5-di-tert-butylanilinet o3 ,4,9,10-perylenetetracarboxylic dianhydride (21) in the presence of zinc acetate in molten imidazole at 130 8C as am eans to generate the monoanhydridew hich could subsequently be reactedw ith nitroxide 22.U nder these condi-Scheme3.Synthetic route to ethynyl-linkedn aphthalimide-based profluorescent nitroxide 14.…”

Section: Resultsmentioning

confidence: 99%

Polyaromatic Profluorescent Nitroxide Probes with Enhanced Photostability

Lussini

Blinco

Fairfull‐Smith

et al. 2015

Chemistry A European J

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Novel profluorescent mono- and bis-isoindoline nitroxides linked to napthalimide and perylene diimide structural cores are described. These nitroxide-fluorophore probes display strongly suppressed fluorescence in comparison to their corresponding non-radical diamagnetic methoxyamine derivatives. The perylene-based probe possessing two isoindoline systems tethered through ethynyl linkages was shown to be the most photostable in solution, demonstrating significantly enhanced longevity over the 9,10-bis(phenylethynyl)anthracene fluorophore used in previous profluorescent nitroxide probes.

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Section: Resultsmentioning

confidence: 99%

Polyaromatic Profluorescent Nitroxide Probes with Enhanced Photostability

Lussini

Blinco

Fairfull‐Smith

et al. 2015

Chemistry A European J

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“…1c) by reaction with primary amines which enables introduction of substituents at the N-atom of the resulting diimides [7].…”

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

Interpreting the near-infrared reflectance of a series of perylene pigments

2013

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. and combination modes of fundamental IR vibrations appear to be more important in explaining the observed variations in NIR reflectance/absorbance. Aromatic groups lead to a small number of intense NIR bands, while alkyl groups generally lead to a greater number of less intense NIR bands. However, neighbouring group effects and/or a molecular dipole moment can substantially alter the intensity of these bands.

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“…prove solubility [26,27] while retaining the planarity of the perylene aromatic ring system, thus preserving the perylene's optical properties. [28] N-substitution of PDIs can also influence their self-assembly properties, which has stimulated intensive studies into bulk ands olution-based applicationso ft hese compounds. [29][30][31][32] By contrast, substitution of the perylener ing system at either the ortho-o rb ay positionsc an significantly influence the optical and solubility properties of the PDIs, dependent upon the substitution pattern, the steric bulk ande lectronic properties of the substituent group.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Self‐Assembly of Bay‐Substituted Perylene Diimide Gemini‐Type Surfactants as Off‐On Fluorescent Probes for Lipid Bilayers

Schill

Dun

Pouderoijen

et al. 2018

Chemistry A European J

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Interest in bay‐substituted perylene‐3,4:9,10‐tetracarboxylic diimides (PDIs) for solution‐based applications is growing due to their improved solubility and altered optical and electronic properties compared to unsubstituted PDIs. Synthetic routes to 1,12‐bay‐substituted PDIs have been very demanding due to issues with steric hindrance and poor regioselectivity. Here we report a simple one‐step regioselective and high yielding synthesis of a 1,12‐dihydroxylated PDI derivative that can subsequently be alkylated in a straightforward fashion to produce nonplanar 1,12‐dialkoxy PDIs. These PDIs show a large Stokes shift, which is specifically useful for bioimaging applications. A particular cationic PDI gemini‐type surfactant has been developed that forms nonfluorescent self‐assembled particles in water (“off state”), which exerts a high fluorescence upon incorporation into lipophilic bilayers (“on state”). Therefore, this probe is appealing as a highly sensitive fluorescent labelling marker with a low background signal for imaging artificial and cellular membranes.

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Synthesis and properties of perylene pigments

Cited by 81 publications

References 25 publications

Polyaromatic Profluorescent Nitroxide Probes with Enhanced Photostability

Polyaromatic Profluorescent Nitroxide Probes with Enhanced Photostability

Interpreting the near-infrared reflectance of a series of perylene pigments

Synthesis and Self‐Assembly of Bay‐Substituted Perylene Diimide Gemini‐Type Surfactants as Off‐On Fluorescent Probes for Lipid Bilayers

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