Search results for "Helicene"

showing 10 items of 16 documents

Synthesis and structural properties of hexaaza[5]helicene containing two [1,2,3]triazolo[1,5-a]pyridine moieties

2013

Abstract We have synthesized a novel hexaaza[5]helicene in a straightforward way from neocuproine. The crystal structure has been elucidated with direct-space strategy TALP which demonstrates the power of the powder X-ray diffraction technique. In this crystal structure it is possible to see an interplanar angle of 33(1)° between the two triazolopyridine rings. The centrosymmetric crystal structure is a racemic mixture, but the resolution was not possible due to a ring-chain isomerization in a solution that produces a dynamic racemization.

010405 organic chemistryStereochemistry[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic ChemistryCrystal structure010402 general chemistry01 natural sciencesBiochemistry0104 chemical sciencesNeocuproinechemistry.chemical_compoundCrystallographychemistryHeliceneDrug DiscoveryPyridineRacemic mixtureTriazolopyridineRacemizationIsomerization
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CCDC 1882076: Experimental Crystal Structure Determination

2019

Related Article: Sebastian B. Beil, Peter Franzmann, Timo Müller, Maximilian M. Hielscher, Tobias Prenzel, Dennis Pollok, Nicole Beiser, Dieter Schollmeyer, Siegfried R. Waldvogel|2018|Electrochimica Acta|302|310|doi:10.1016/j.electacta.2019.02.041

914-bis(ethoxycarbonyl)-2367-tetramethoxy[5]heliceneSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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Novel [6]- and [7]Helicene-Like Quinones via Mono- and Bidirectional Chromium-Templated Benzannulation of Bridged Binaphthyl Carbene Complexes

2005

A new organometallic approach to novel, functionalised, helicene-like quinones and bisquinones has been developed based on the chromium-templated [3+2+1] benzannulation reaction. The [5]helicene-analogous monocarbene chromium complexes 4, 5, 17 and 19, derived from dibromo-substituted methylene- or silylene-tethered binaphthols 2 and 3, react with various alkynes to give [6]helicene-like quinones 6–13 and 20–29 after oxidative work-up. A rare competition of angular vs. linear annulation is observed for the incorporation of phenylacetylene that affords quinones 21/22 and 28/29. Protection of the phenolic benzannulation product with camphanic acid chloride 14, followed by chromatographic sepa…

AnnulationChemistryStereochemistryArylOrganic ChemistryCrystal structureMedicinal chemistrychemistry.chemical_compoundEnantiopure drugHelicenePhenylacetylenePhysical and Theoretical ChemistryMethyleneCarbeneEuropean Journal of Organic Chemistry
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A theoretical and experimental study of the racemization process of hexaaza[5]helicenes

2014

A dynamic 1H NMR study, together with DFT calculations, of bis-([1,2,3]triazolo)[1,5-a:5′,1′-k][1,10]phenanthroline 2 has allowed to identify the ring and open forms of a new example of ring/chain tautomerism, as well as their interconversion barriers (ring/ring and ring/open). The barrier of the exchange process between the chain forms and the ring form was found higher than the 'racemization' process in the closed form, so the ring opening does not contribute to the 'racemization'. The di-1,10-methyl and di-1,10-iodo derivatives have been prepared and their properties calculated.

Helical chirality[CHIM.ORGA]Chemical Sciences/Organic chemistryStereochemistryPhenanthrolineOrganic ChemistryRing (chemistry)BiochemistryTautomer3. Good healthRacemization barrierschemistry.chemical_compoundAzahelicenesChain (algebraic topology)chemistryComputational chemistryDrug DiscoveryProton NMRDiazoimine–triazole equilibriumRacemizationTetrahedron
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Amplification of Dissymmetry Factors in π-Extended [7]- and [9]Helicenes

2021

International audience; $\pi$-Extended helicenes constitute an important class of polycyclic aromatic hydrocarbons with intrinsic chirality. Herein, we report the syntheses of $\pi$extended [7]helicene $4$ and $\pi$-extended [9]helicene $6$ through regioselective cyclodehydrogenation in high yields, where a "prefusion" strategy plays a key role in preventing undesirable aryl rearrangements. The unique helical structures are unambiguously confirmed by X-ray crystal structure analysis. Compared to the parent pristine [7]helicene and [9]helicene, these novel $\pi$-extended helicenes display significantly improved photophysical properties, with a quantum yield of 0.41 for $6$. After optical res…

Models MolecularMolecular StructureChemistryArylRegioselectivityQuantum yieldStereoisomerismGeneral ChemistryCrystal structure010402 general chemistry01 natural sciencesBiochemistryArticleCatalysis0104 chemical sciences3. Good healthchemistry.chemical_compoundCrystallographyColloid and Surface ChemistryHelicene[CHIM]Chemical SciencesPolycyclic CompoundsEnantiomerLuminescenceChirality (chemistry)
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CCDC 146055: Experimental Crystal Structure Determination

2000

Related Article: H.Meier, M.Schwertel, D.Schollmeyer|2000|Acta Crystallogr.,Sect.C:Cryst.Struct.Commun.|56|684|doi:10.1107/S0108270100003140

Space GroupCrystallography413-(18 Octamethylenedioxy)hexaheliceneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 2004421: Experimental Crystal Structure Determination

2020

Related Article: Zijie Qiu, Sobi Asako, Yunbin Hu, Cheng-Wei Ju, Thomas Liu, Loïc Rondin, Dieter Schollmeyer, Jean-Sébastien Lauret, Klaus Müllen, Akimitsu Narita|2020|J.Am.Chem.Soc.|142|14814|doi:10.1021/jacs.0c05504

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters1823-di-t-butyl-1213-ethenocyclohepta[uvwxyz]dibenzo[45:67]cyclohepta[123-gh]phenanthro[9101-jkl]hexahelicene dichloromethane solvateExperimental 3D Coordinates
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CCDC 2021692: Experimental Crystal Structure Determination

2020

Related Article: Zijie Qiu, Sobi Asako, Yunbin Hu, Cheng-Wei Ju, Thomas Liu, Loïc Rondin, Dieter Schollmeyer, Jean-Sébastien Lauret, Klaus Müllen, Akimitsu Narita|2020|J.Am.Chem.Soc.|142|14814|doi:10.1021/jacs.0c05504

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters1823-di-t-butyl-1213-ethenocyclohepta[uvwxyz]dibenzo[45:67]cyclohepta[123-gh]phenanthro[9101-jkl]hexahelicene tetrahydrofuran solvateExperimental 3D Coordinates
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CCDC 2047541: Experimental Crystal Structure Determination

2021

Related Article: Zijie Qiu, Cheng-Wei Ju, Lucas Frédéric, Yunbin Hu, Dieter Schollmeyer, Grégory Pieters, Klaus Müllen, Akimitsu Narita|2021|J.Am.Chem.Soc.|143|4661|doi:10.1021/jacs.0c13197

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters2023-di-t-butyldibenzo[56:78]pentapheno[1141312-ijklmno]heptahelicene chloroform solvateExperimental 3D Coordinates
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CCDC 146054: Experimental Crystal Structure Determination

2000

Related Article: H.Meier, M.Schwertel, D.Schollmeyer|2000|Acta Crystallogr.,Sect.C:Cryst.Struct.Commun.|56|684|doi:10.1107/S0108270100003140

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters413-(110-Decamethylenedioxy)hexaheliceneExperimental 3D Coordinates
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