Herein, we report the one-pot synthesis of an electron-poor nanographene containing dicarboximide groups at the corners. We efficiently combined palladium-catalyzed Suzuki-Miyaura cross-coupling and dehydrohalogenation to synthesize an extended two-dimensional π-scaffold of defined size in a single chemical operation starting from N-(2,6-diisopropylphenyl)-4,5-dibromo-1,8-naphthalimide and a tetrasubstituted pyrene boronic acid ester as readily accessible starting materials. The reaction of these precursors under the conditions commonly used for Suzuki-Miyaura cross-coupling afforded a C64 nanographene through the formation of ten C-C bonds in a one-pot process. Single-crystal X-ray analysis unequivocally confirmed the structure of this unique extended aromatic molecule with a planar geometry. The optical and electrochemical properties of this largest ever synthesized planar electron-poor nanographene skeleton were also analyzed.
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http://dx.doi.org/10.1002/anie.201601433 | DOI Listing |
Angew Chem Int Ed Engl
August 2024
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Near-Infrared (NIR) phosphorescence at room temperature is challenging to achieve for organic molecules due to negligible spin-orbit coupling and a low energy gap leading to fast non-radiative transitions. Here, we show a supramolecular host-guest strategy to harvest the energy from the low-lying triplet state of C nanographene tetraimide 1. H NMR and X-ray analysis confirmed the 1 : 2 stoichiometric binding of a Pt(II) porphyrin on the two π-surfaces of 1.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
June 2023
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Phthalocyanines are extensively used by the dye and pigment industry and in photovoltaic and photodynamic therapy research due to their intense absorption of visible light, outstanding stability, and versatility. As pigments, the unsubstituted phthalocyanines are insoluble owing to strong intermolecular π-π-stacking interactions, which causes limitations for the solution chemistry for both free base and metalated phthalocyanines. Here we show a supramolecular host-guest strategy to dissolve phthalocyanines into solution.
View Article and Find Full Text PDFNat Chem
April 2022
Institut für Organische Chemie, Universität Würzburg, Würzburg, Germany.
Polycyclic aromatic hydrocarbons (PAHs) show promise for applications in functional devices such as organic photovoltaics and field-effect transistors, but, although nanometre-sized PAHs-often referred to as nanographenes-have been well investigated as single-layer molecules, their multilayer counterparts remain rather unexplored. Here we show the assembly of a C nanographene derivative (comprising a planar core decorated with four meta-terphenyl-imide moieties at its periphery) into multilayer stacks with smaller PAHs ranging from naphthalene to ovalene and hexabenzocoronene. The functionalized C nanographene serves as a ditopic host that can accommodate a smaller PAH on either side of its planar core, in cavities delimited by its bulky imide substituents.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
May 2016
Universität Würzburg, Institut für Organische Chemie and Center for Nanosystems Chemistry, Am Hubland, 97074, Würzburg, Germany.
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