NDLI: Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core

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Organic & Biomolecular Chemistry Vol -15

Organic & Biomolecular Chemistry Vol -9

Organic & Biomolecular Chemistry Vol - 9 Issue - 24

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Construction of a tunable metallohydrolase center on an invertible molecular pocket

An efficient copper-catalyzed synthesis of anilines by employing aqueous ammonia

CF₂-Containing acetylenephosphonates in heterocyclization reactions: the first synthesis of 2-difluoromethyl azaxanth-3-ylphosphonates

Functionalized 2,3-dihydrofurans via palladium-catalyzed oxyarylation of α-allyl-β-ketoesters

Thiacalix[4]arene based reconfigurable molecular switches: set-reset memorized sequential device

Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core

An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones

4′-Alkoxy oligodeoxynucleotides: a novel class of RNA mimics

Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state

Pyridinium/urea-based anion receptor: methine formation in the presence of basic anions

Versatile trifunctional chemosensor of rhodamine derivative for Zn²⁺, Cu²⁺ and His/Cys in aqueous solution and living cells

Synthesis and biological properties of conjugates between fluoroquinolones and a N3′′-functionalized pyochelin

Synthesis and biological evaluation of potential new inhibitors of the bacterial transferase MraY with a β-ketophosphonate structure

Cyclohexyl “base pairs” stabilize duplexes and intensify pyrene fluorescence by shielding it from natural base pairs

Sulfonamide carbazole receptors for anion recognition

One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol

Bis- and tris-naphthoimidazolium derivatives for the fluorescent recognition of ATP and GTP in 100% aqueous solution

Facile aromatic radiofluorination of [¹⁸F]flumazenil from diaryliodonium salts with evaluation of their stability and selectivity

Synthesis of a library of oligothiophenes and their utilization as fluorescent ligands for spectral assignment of protein aggregates

Exploring the synthetic potency of the first furanothioglycoligase through original remote activation

Three-component, one-pot sequential synthesis of glyco-hydantoin conjugates

A new practical synthesis of triaryl and trisindolylmethanes under solvent-free reaction conditions

Predicting Michael-acceptor reactivity and toxicity through quantum chemical transition-state calculations

Divergent synthetic approach to 6′′-modified α-GalCer analogues

An efficient strategy for the general synthesis of 3-aryl substituted pyrazolo[5,1-c][1,4]benzoxazines and pyrazolo[1,5-a][1,4]benzodiazepin-6(4H)-ones

Highly efficient aldol additions of DHA and DHAP to N-Cbz-amino aldehydes catalyzed by l-rhamnulose-1-phosphate and l-fuculose-1-phosphate aldolases in aqueous borate buffer

Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones

The reactivity of quaternary ammonium- versus potassium- fluorides supported on metal oxides: paving the way to an instantaneous detoxification of chemical warfare agents

Highly diastereoselective Friedel–Crafts reaction of arenes with N-tert-butanesulfinylimino ester towards the efficient synthesis of α-arylglycines

A new cyclopamine glucuronide prodrug with improved kinetics of drug release

Synthesis of 1,2,3-triazole linked galactopyranosides and evaluation of cholera toxin inhibition

Pyridoxine-derived bicyclic aminopyridinol antioxidants: synthesis and their antioxidant activities

Multi-component, regio-selective aldol addition of β-ketoesters to aldehydes: scope and applications

C₃-triiodocyclotriveratrylene as a key intermediate to fluorescent probes: application to selective choline recognition

Improvement of in vitro-transcribed amber suppressor tRNAs toward higher suppression efficiency in wheat germ extract

Additions and corrections published in 2011

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Organic & Biomolecular Chemistry Vol - 9 Issue - 19

Organic & Biomolecular Chemistry Vol - 9 Issue - 9

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Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core

Content Provider	Royal Society of Chemistry (RSC)
Author	Vauthey, Eric Petkova, Irina Fin, Andrea Matile, Stefan Doval, David Alonso Sakai, Naomi
Copyright Year	2011
Abstract	The green-fluorescent protein of the jellyfish operates with the most powerful phenolate donors in the push–pull fluorophore. To nevertheless achieve red fluorescence with the same architecture, sea anemone and corals apply oxidative imination, a process that accounts for the chemistry of vision as well. The objective of this study was to apply these lessons from nature to one of the most compact family of panchromatic fluorophores, i.e. core-substituted naphthalenediimides (cNDIs). We report straightforward synthetic access to hydroxylated cNDI and cPDI cores by palladium-catalyzed cleavage of allyloxy substituents. With hydroxylated cNDIs but not cPDIs in water-containing media, excited-state intramolecular proton transfer yields a second bathochromic emission. Deprotonation of hydroquinone, catechol and boronic ester cores provides access to an impressive panchromism up to the NIR frontier at 640 nm. With cNDIs, oxidative imination gives red shifts up to 638 nm, whereas the expanded cPDIs already absorb at 754 nm upon deprotonation of hydroquinone cores. The practical usefulness of hydroquinone cNDIs is exemplified by ratiometric sensing of the purity of DMF with the “naked eye” at a sensitivity far beyond the “naked nose”. We conclude that the panchromatic hypersensitivity toward the environment of the new cNDIs is ideal for pattern generation in differential sensing arrays.
Starting Page	8246
Ending Page	8252
Page Count	7
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	24
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c1ob05702b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Excited state intramolecular proton transfer Pacte de Famille Hypersensitivity Sea anemone Fluorescence Catechol Protein Hydroquinone Organic chemistry Jellyfish Fluorophore NIR Boronic acid Panchromatic film Push\u2013pull train
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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Detection of Boronic Acids through Excited-State Intramolecular Proton-Transfer Fluorescence

Fluorophore with Two-Photon-Excited and Emissive Behaviors in the NIR Region

Red-Shift (2-Hydroxyphenyl)-Benzothiazole Emission by Mimicking the Excited-State Intramolecular Proton Transfer Effect

Detection of Boronic Acids through Excited-State Intramolecular Proton-Transfer Fluorescence

Intramolecular interactions in ortho-methoxyalkylphenylboronic acids and their catechol esters.

Naphthalene Diols: A New Class of Antioxidants Intramolecular Hydrogen Bonding in Catechols, Naphthalene Diols, and Their Aryloxyl Radicals

Light-emitting organic nanoaggregates from functionalized p-quaterphenylenes

Excited-state intramolecular proton transfer in jet-cooled 2,5-bis(2-benzothiazolyl)hydroquinone.

“Push-no-pull” porphyrins for second harmonic generation imaging

Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core

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Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core