Dominik Lungerich

Zig-zag nanographenes are promising candidates for the applications in organic electronics due to the electronic properties induced by their periphery. However, the synthetic access to these compounds remains virtually unexplored. There is a lack in efficient and mild strategies origins in the reduced stability, increased reactivity, and low solubility of these compounds. Herein we report a facile access to pristine zig-zag nanographenes, utilizing an acid-promoted intramolecular reductive cycli

A free-base porphyrin carrying two hexabenzocoronene (HBC) substituents in a trans arrangement and its zinc complex have been prepared. The compounds were characterized extensively and found to form tricationic dimers in the gas phase. X-ray crystallography confirms for the zinc complex a profound π-stacking of the HBC moieties. In contrast, the free-base porphyrin incarcerates n-heptane which essentially prevents π-stacking. Upon excitation of the HBC substituents, efficient energy transfer to

A novel rational synthetic pathway-the "functionalization of para-nitroaniline" (FpNA)-provides substituted hexaarylbenzenes (HABs) with uncommon symmetries that bear up to five different substituents, fully avoiding regioisomeric product distributions during the reactions. 4-Nitroaniline is functionalized by a cascade of electrophilic halogenations, Sandmeyer brominations, and Suzuki cross-coupling reactions, leading to 26 substitution geometries, of which 18 structures are not available by the

Single-molecule electronic components (SMECs) are envisioned as next-generation building blocks in quantum circuit systems. However, challenges such as the reproducibility of the electrode attachment to the individual molecules hamper their fundamental investigation. For our purpose, we introduced quasi optoelectronic electrodes (QOEs) that allow for rapid investigations of the properties and suitability of compounds for molecular electronic devices. In particular, we probed hexa-peri-hexabenzoc

The rising prospects of mechanochemically assisted syntheses hold promise for both academia and industry, yet they face challenges in understanding and, therefore, anticipating respective reaction kinetics. Particularly, dependencies based on variations in milling equipment remain little understood and globally overlooked. This study aims to address this issue by identifying critical parameters through kinematic models, facilitating the reproducibility of mechanochemical reactions across the mos

A feasible two-step synthesis and characterization of a full series of hexaarylbenzene (HAB) substituted porphyrins and tetrabenzoporphyrins is presented. Key steps represent the microwave-assisted porphyrin condensation and the statistical Diels-Alder reaction to the desired HAB-porphyrins. Regarding their applications, they proved to be easily accessible and effective high molecular mass calibrants for (MA)LDI mass spectrometry. The free-base and zinc(II) porphyrin systems, as well as the resp

Abstract Ein nichtmetalliertes Porphyrin mit zwei trans‐ständigen Hexabenzocoronen(HBC)‐Substituenten und der zugehörige Zinkkomplex wurden hergestellt. Die Verbindungen wurden ausführlich untersucht, und es zeigte sich, dass sie in der Gasphase trikationische Dimere bilden. Die Röntgenstrukturanalyse des Zinkkomplexes ergab eine ausgeprägte π‐Stapelwechselwirkung, wohingegen beim nichtmetallierten Porphyrin n‐Heptan interkaliert, was die π‐Stapelung weitgehend verhindert. Die Anregung der HBC‐S

Inspired by light-induced processes in nature to mimic the primary events in the photosynthetic reaction centers, novel functional materials combine electron donors and acceptors, i.e., (metallo)porphyrins (ZnP) and fullerenes (C₆₀), respectively, with emerging materials, i.e., nanographenes. We utilized hexa-<i>peri</i>-hexabenzocoronene (HBC) due to its versatility regarding functionalization and physicochemical properties, to construct three regioisomeric ZnP-HBC-C₆₀ con

Invited for the cover of this issue are the groups of Lungerich and Jux at the Friedrich-Alexander University Erlangen-Nuernberg. The image depicts the synthetic feasibility with a "TATBP tuning shop", which shows the change of the four meso aryl substituents to modify the performance of the molecule. Read the full text of the article at 10.1002/chem.201904718.

Singular reaction events of small molecules and their dynamics remain a hardly understood territory in chemical sciences since spectroscopy relies on ensemble-averaged data, and microscopic scanning probe techniques show snapshots of frozen scenes. Herein, we report on continuous high-resolution transmission electron microscopic video imaging of the electron-beam-induced bottom-up synthesis of fullerene C₆₀ through cyclodehydrogenation of tailor-made truxene derivative <b>1</b> (C<sub

A systematic series of superbenzene-porphyrin conjugates was synthesized and characterized. All conjugates show a high degree of cluster formation that correlates to the amount of tert-butylated hexa-peri-hexabenzocoronenes (tBuHBCs) attached to the porphyrin's periphery. Determined by mass spectrometry and X-ray diffraction, van der Waals (vdW) interactions like London dispersions (LD), stemming from solubilizing tert-butyl groups, were identified to be the major reason for the cluster formatio

Abstract Erstmals ist es gelungen, einen rationalen Syntheseplan – die “Funktionalisierung von para‐Nitroanilin” (FpNA) – zur Herstellung substituierter Hexaarylbenzole (HABs) mit ungewöhnlichen Symmetrien und mit bis zu fünf verschiedenen Substituenten zu realisieren. Dabei konnte jegliches Auftreten regioisomerer Produktverteilungen während der Reaktion ausgeschlossen werden. 4‐Nitroanilin wird dabei in einer Kaskade von elektrophilen Halogenierungen, Sandmeyer‐Bromierungen und Suzuki‐Kupplung

New insights into [18]annulene were gained by looking more closely at its X-ray structure, revealing a close face-to-face stacking of 3.16 Å in a herringbone-like crystal packing. Hexadehydro[18]annulene was co-crystalized in a benzene matrix, demonstrating the stabilizing role of intercalated solvent molecules in solid annulenes.

Abstract Auf Einzelmolekülen basierende elektronische Bauteile werden als nächste Generation für nanoelektronische Schaltkreise angesehen. Herausforderungen wie etwa die reproduzierbare Kontaktierung von Elektroden an die jeweiligen Moleküle stehen jedoch der fundamentalen Untersuchung dieser Systeme im Wege. Deshalb stellen wir das Konzept der quasi‐optoelektronischen Elektroden (QOEs) vor, welches die schnelle Untersuchung der Eigenschaften und die Eignung chemischer Verbindungen für molekular

Geodesic nitrogen-containing graphene fragments are interesting candidates for various material applications, but the available synthetic protocols, which need to overcome intrinsic strain energy during the formation of the bowl-shaped skeletons, are often incompatible with heteroatom-embedded structures. Through this mass spectrometry-based gas-phase study, we show by means of collision-induced dissociation experiments and supported by density functional theory calculations, the first evidence