Correction for 'Fluorescence of a chiral pentaphene derivative derived from the hexabenzocoronene Motif' by Philipp Rietsch et al., Chem. Commun., 2019, 55, 10515-10518.
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Synthesis and Characterizations of 5,5'-Bibenzo[rst]pentaphene with Axial Chirality and Symmetry-Breaking Charge Transfer.
Adv Sci (Weinh)
July 2022
Max Planck Institute for Polymer Research, Ackermannweg 10, Mainz, 55128, Germany.
Exploration of novel biaryls consisting of two polycyclic aromatic hydrocarbon (PAH) units can be an important strategy toward further developments of organic materials with unique properties. In this study, 5,5'-bibenzo[rst]pentaphene (BBPP) with two benzo[rst]pentaphene (BPP) units is synthesized in an efficient and versatile approach, and its structure is unambiguously elucidated by X-ray crystallography. BBPP exhibits axial chirality, and the (M)- and (P)-enantiomers are resolved by chiral high-performance liquid chromatography and studied by circular dichroism spectroscopy.
View Article and Find Full Text PDFHelically Arranged Chiral Molecular Nanographenes.
J Am Chem Soc
August 2021
Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain.
A benchtop solution-phase synthesis of molecular nanographenes composed of two orthogonal dibenzo[fg,ij]phenanthro[9,10,1,2,3-pqrst]pentaphene (DBPP) moieties covalently connected through a tetrafluorobenzene ring is described. The helical arrangement of these three covalently linked molecular fragments leads to the existence of a chiral axis which gives rise to a racemic mixture, even with the molecular moieties being symmetrically substituted. X-ray diffraction studies show that both enantiomers cocrystallize in a single crystal, and the racemic mixture can be resolved by chiral HPLC.
View Article and Find Full Text PDFCorrection: Fluorescence of a chiral pentaphene derivative derived from the hexabenzocoronene Motif.
Chem Commun (Camb)
November 2019
Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, Berlin, 14195, Germany.
Correction for 'Fluorescence of a chiral pentaphene derivative derived from the hexabenzocoronene Motif' by Philipp Rietsch et al., Chem. Commun.
View Article and Find Full Text PDFFluorescence of a chiral pentaphene derivative derived from the hexabenzocoronene Motif.
Chem Commun (Camb)
August 2019
Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, Berlin, 14195, Germany.
A new fluorescent pentaphene derivative is presented that differs from hexabenzocoronene (HBC) by one carbon atom in the basal plane skeleton. A 500% increased fluorescence quantum yield is measured compared to the HBC derivative. The pentaphene compound, obtained by a modified Scholl oxidation, is also emissive in the solid-state, due to the packing motif in the crystal.
View Article and Find Full Text PDFAxially chiral facial amphiphiles with a dihydronaphthopentaphene structure as molecular tweezers for SWNTs.
Chemistry
October 2009
Laboratory of Functional Chemo-Systems, UMR 7199, Faculté de Pharmacie, Université de Strasbourg, 74 Route du Rhin, BP 24, 67401 Illkirch, France.
Syntheses of chiral 6,15-dihydronaphtho[2,3-c]pentaphene derivatives of opposite configurations are reported. Starting from anthracene, the strategy involves two key steps: a Diels-Alder reaction on a prochiral dianthraquinone, and an enantiomeric resolution using (-)-menthol. The final molecules exhibit very strong optical activity, as shown by their circular dichroism spectra, and are examples of chiral facial amphiphiles.
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