
Dominik Lungerich
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Tuning Singlet Fission in π-Bridge-π Chromophores
Contorted polycyclic aromatic hydrocarbons with cove regions and zig-zag edges
DOI: 10.1039/C7CC03709K, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Three tetrapyrene-fused benzocoronenes were synthesized by a "bottom-up" approach, which offers a facile access to extended polycyclic aromatic hydrocarbons with cove regions and zig-zag edges.
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Closed-shell paramagnetic porphyrinoids
DOI: 10.1039/C7CC05232D, Communication
Magnetizabilities and magnetically induced ring-current strength susceptibilities have been calculated at the Hartree-Fock, density functional theory and second order Moller-Plesset levels for a number of antiaromatic closed-shell carbaporphyrins, carbathiaporphyrins and isophlorins.
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Porphyrinoid rotaxanes: building a mechanical picket fence
DOI: 10.1039/C7SC03165C, Edge Article
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
We demonstrate that the threaded macrocycles in interlocked porphyrin-corrole conjugates provide a mechanical "picket fence" without affecting their electronic properties.
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Pentagon-Embedded Cycloarylenes with Cylindrical Shapes
Multiple pentagons were synthetically embedded in cylinder-shaped molecules to obtain segments of haeckelite nanotubes with imperfect honeycomb arrays. In these cylinder-shaped molecules, conjugation was observed over the pentagon bridges. These compounds also provide intermediate structures for retrosynthetic analysis and inspiration for novel defective carbon nanotubes.
[Communication]
Shunpei Hitosugi, Sota Sato, Taisuke Matsuno, Takashi Koretsune, Ryotaro Arita, Hiroyuki Isobe
Angew. Chem. Int. Ed., June 29, 2017, https://doi.org/10.1002/anie.201704676 Read article
Cyclopenta Ring Fused Bisanthene and Its Charged Species with Open-Shell Singlet Diradical Character and Global Aromaticity/ Anti-Aromaticity
Good character: Cyclopenta ring fused bisanthene (middle) was facilely synthesized and shows global anti-aromaticity with moderate diradical character. The dication exhibits a unique [10]annulene-within-[18]annulene structure with an open-shell singlet ground state, while the dianion is a closed shell and displays a diatropic ring current on the π-conjugated periphery.
[Communication]
Qing Wang, Tullimilli Y. Gopalakrishna, Hoa Phan, Tun Seng Herng, Shaoqiang Dong, Jun Ding, Chunyan Chi
Angew. Chem. Int. Ed., June 29, 2017, https://doi.org/10.1002/anie.201704805 Read article
Thermal Disproportionation of Oxo-Functionalized Graphene
Losing O's: Graphene can be prepared by heating oxo-functionalized graphene. Defunctionalization resulting in graphene formation (path I) is the dominant process.
[Communication]
Fabian Grote, Christoph Gruber, Felix Börrnert, Ute Kaiser, Siegfried Eigler
Angew. Chem. Int. Ed., June 30, 2017, https://doi.org/10.1002/anie.201704419 Read article
"Inverted" porphyrins: a distorted adsorption geometry of free-base porphyrins on Cu(111)
DOI: 10.1039/C7CC04182A, Communication
Peculiar "inverted" intramolecular conformation of a free-base porphyrin due to specific attractive molecule-substrate interaction.
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Configurational Stability of [5]Helicenes
The K-Region in Pyrenes as a Key Position to Activate Aggregation-Induced Emission: Effects of Introducing Highly Twisted N,N-Dimethylamines
Porphyrin Arch-Tapes: Synthesis, Contorted Structures, and Full Conjugation
Pyreniporphyrins: Porphyrin Analogues That Incorporate a Polycyclic Aromatic Hydrocarbon Subunit within the Macrocyclic Framework
Dithiafulvenyl-Extended N-Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence
Abstract
We describe the synthesis as well as the electronic and photophysical characterization of novel N-heterotriangulene derivatives decorated with methoxycarbonyl- and methyl-sulfanyl-substituted dithiafulvenyl moieties. The association of these electron-rich compounds with fullerene C60 as electron acceptor was investigated by means of photophysical, voltammetric, and mass spectrometric methods and rationalized by DFT calculations. Importantly, light-induced interactions between the dithiafulvene-substituted N-heterotriangulene bearing methoxycarbonyl substituents with C60 leads to cooperative fluorescence. Quantitative Job plot analyses by means of fluorescence spectroscopy and voltammetry confirm a 1:1 association with binding constants in the order of 104 m−1. Supportive results for the supramolecular assembly of both N-heterotriangulenes with C60 were obtained by ESI mass spectrometric investigations in the gas phase.
Enlightened association: Electron-rich N-heterotriangulenes featuring dithiafulvenyl moieties were synthesized and their association with C60 resulting in cooperative fluorescence was studied by photophysical, voltammetric, and mass spectrometric methods and rationalized by DFT calculations.
Odd [n]Cumulenes (n = 3, 5, 7, 9): Synthesis, Characterization, and Reactivity
Base-Selective Five- versus Six-Membered Ring Annulation in Palladium-Catalyzed C–C Coupling Cascade Reactions: New Access to Electron-Poor Polycyclic Aromatic Dicarboximides
Polycycles: Depending on the auxiliary bases applied in Pd-catalyzed C−C coupling reactions electron-poor polycyclic aromatic hydrocarbons are obtained by selective five- or six-membered ring annulation.
[Communication]
Sabine Seifert, David Schmidt, Kazutaka Shoyama, Frank Würthner
Angew. Chem. Int. Ed., May 23, 2017, https://doi.org/10.1002/anie.201702889 Read article
A Modular Flow Design for the meta-Selective C−H Arylation of Anilines
One by one or all in one: meta-Arylated anilines are key moieties in a variety of high-value chemicals. To access these compounds, four key flow steps were identified, including synthesis of the diaryliodonium salt, meta-selective C−H arylation, and the removal of both the copper catalyst and the directing group. Each module has great individual potential, however, combining them allowed straightforward access to meta-arylated anilines within a reasonable time scale and with good purity.
[Communication]
Hannes P. L. Gemoets, Gabriele Laudadio, Kirsten Verstraete, Volker Hessel, Timothy Noël
Angew. Chem. Int. Ed., May 22, 2017, https://doi.org/10.1002/anie.201703369 Read article
Synthesis, Properties, and Semiconducting Characteristics of BF2 Complexes of β,β-Bisphenanthrene-Fused Azadipyrromethenes
Synthesis of a Three-Bladed Propeller-Shaped Triple [5]Helicene
The first molecular dumbbell consisting of an endohedral Sc3N@C80 and an empty C60-fullerene building block
DOI: 10.1039/C7CC03012F, Communication
Unprecedented synthesis of a fullerene dumbbell consisting of an endohedral metallic Sc3N@C80 and an empty C60 fullerene which reveals an exceptional electronic behaviour.
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A Twisted Nanographene Consisting of 96 Carbon Atoms
A new type of twisted nanographene containing an [8]circulene moiety in a polycyclic framework of 96 sp2 carbon atoms was synthesized from a macrocyclic diyne (see picture). Its structure was studied with X-ray crystallography and DFT calculations.
[Communication]
Kwan Yin Cheung, Chi Kit Chan, Zhifeng Liu, Qian Miao
Angew. Chem. Int. Ed., May 16, 2017, https://doi.org/10.1002/anie.201703754 Read article
meso-Cumulenic 2H-Corroles from meso-Ethynyl-3H-corroles
A π-conjugated dumbbell: [5]Cumulene-bridged 2H-corrole dimers capable of accommodating ZnII ions are synthesized from the corresponding meso-alkynyl-substituted 3H-corroles (see scheme). Their structures are revealed by X-ray diffraction analysis and the bond-length alternations in the cumulene segments are slightly larger than in conventional [n]cumulenes.
[Communication]
Kento Ueta, Koji Naoda, Shota Ooi, Takayuki Tanaka, Atsuhiro Osuka
Angew. Chem. Int. Ed., May 16, 2017, https://doi.org/10.1002/anie.201703139 Read article
Crystal-Packing-Driven Enrichment of Atropoisomers
Turn up the amplification: Solid-state heating of a mixture containing seven atropostereo-isomers converts almost all its components into a single product. This process takes place, even though the amplified stereoisomer represents only a minor (<25 mol %) component of the mixture at equilibrium in solution. Favorable crystal-packing interactions induce the high selectivity observed in this process.
[Communication]
Mona Sharafi, Joseph P. Campbell, Sinu C. Rajappan, Natavan Dudkina, Danielle L. Gray, Toby J. Woods, Jianing Li, Severin T. Schneebeli
Angew. Chem. Int. Ed., May 16, 2017, https://doi.org/10.1002/anie.201701876 Read article
Synthesis of Tetraaza[8]circulenes from Tetrathia[8]circulenes through an SNAr-Based Process
Synthesis of Long Oxahelicenes by Polycyclization in a Flow Reactor
Think big: Oxahelicenes comprising up to 19 fused rings (see example) were synthesized by multiple cobalt(I)-mediated cycloisomerization reactions of oligoynes, most efficiently in a flow reactor. The stereogenic centers in enantiomerically pure substrates steered the diastereoselective polycyclization of the oligoynes. Single-molecule conductivity was studied in a pyridooxa[9]helicene by the break-junction method.
[Communication]
Jindřich Nejedlý, Michal Šámal, Jiří Rybáček, Miroslava Tobrmanová, Florence Szydlo, Christophe Coudret, Maria Neumeier, Jaroslav Vacek, Jana Vacek Chocholoušová, Miloš Buděšínský, David Šaman, Lucie Bednárová, Ladislav Sieger, Irena G. Stará, Ivo Starý
Angew. Chem. Int. Ed., April 18, 2017, https://doi.org/10.1002/anie.201700341 Read article






















