Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• unambiguously proving the formation of tetracene 57. Importantly, the oxygen atoms extruded from precursor 56 were observed on the copper surface in close proximity to the converted molecule. In contrast with this tip-induced conversion of soluble precursor 56, which occurs stepwise and gives rise to one single

• target molecule after each manipulation cycle, thermal activation of the population of adsorbed diepoxides 56 was next attempted. Annealing at 120 °C for 5 min successfully promoted the O-extrusion to yield the corresponding tetracene molecules, without any trace of partially-converted monoepoxide

• -dihydrothiophene 1-oxides [79]. SO-extrusion as a key step in the synthesis of fullerenes (C60 and C70) encapsulating H2 molecules [80][82]. Synthesis of diepoxytetracene precursor 56 and its on-surface conversion into tetracene upon O-extrusion. Inset in the top right shows a Laplace-filtered AFM image of a

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• -catalyzed formal [2 + 2] cycloaddition reactions but also the emergence of tetracene trimer 86 and tetramer 88 stemming from [2 + 2 + 2] cycloaddition reactions (Scheme 18). It is proposed that an aryne intermediate is formed after thermal activation and that the observed end products are formed from arynes

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• 1H NMR and NOESY NMR imply the dependence of molecular symmetry on the type of spacer. The ability of synthesized dimers to increase the solubility of tetracene in DMSO was evaluated and compared to native cyclodextrins and their methylated derivatives. The newly synthesized compounds expressed

• better effectiveness than other tested supramolecular hosts. Keywords: cyclodextrin; dimer; methylation; solubilization; tetracene; Introduction Cyclodextrins (CDs) are cyclic oligomers of glucose that play an important role in supramolecular chemistry [1]. The structure of any CD contains a

• unstable, for example, towards oxidation. So, we have chosen tetracene as the object of our research. This molecule is also known as an organic semiconductor and is poorly soluble, but it demonstrates some stability to oxidation, making it easier to work with. We assumed these results might be extended to

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• anthracene, tetracene, and naphtho[b]thiophene derivatives via ZnBr2-mediated regioselective annulation of asymmetric 1,2-diarylmethine dipivalates 83a (Scheme 20). On the basis of this methodology, they prepared 37 examples of different types of anthracene derivatives, such as compounds 84a–e, in very good

Adhesion, forces and the stability of interfaces

• Robin Guttmann,
• Johannes Hoja,
• Christoph Lechner,
• Reinhard J. Maurer and
• Alexander F. Sax

Beilstein J. Org. Chem. 2019, 15, 106–129, doi:10.3762/bjoc.15.12

Steric “attraction”: not by dispersion alone

• Ganna Gryn’ova and
• Clémence Corminboeuf

Beilstein J. Org. Chem. 2018, 14, 1482–1490, doi:10.3762/bjoc.14.125

• representative class (II) and class (III) systems: tetracene (7) and its fully saturated analogue, perhydrotetracene (10, Figure 5A and B). For each monomer, four types of dimers were compared – perfectly stacked (i.e., the frozen dimer) and shifted transversally, laterally and in both directions by approx. half

• the ring (Figure S11 in Supporting Information File 1). The main purpose of this exercise is to mimic the results of geometrical relaxation with and without the charge penetration for a diverse sample of dimer arrangements, i.e., beyond the model frozen and optimized geometries. For tetracene, the

• shifted dimer is energetically favored, while for perhydrotetracene the stacked dimer is preferred. Our results in Figure 5C comparing selected – shifted and stacked – dimers (see all four dimers comparison in Figure S11 in Supporting Information File 1) illustrate that in tetracene (7) neglecting the

Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene

• Laurence Burroughs,
• John Ritchie,
• Mkhethwa Ngwenya,
• Dilfaraz Khan,
• William Lewis and
• Simon Woodward

Beilstein J. Org. Chem. 2015, 11, 273–279, doi:10.3762/bjoc.11.31

• eliminations. Structural packing motifs and electronic properties are reported for the tetracenes. Keywords: allenes; anionic Chugaev rearrangement; anionic sigmatropic rearrangement; tetracene properties; X-ray structures; Introduction In recent years polyacenes, especially tetra- and pentacenes, have been

• cascade approach for rapid access to tetracene sulfoxides in 2007 (Scheme 1). In 2012 Liu used a Pd-based strategy to provide 12-substituted 5-aryltetracenes [after final trapping with RB(OH)2)] [16]. Both of these reactions rely on the formation of bis-allenes 2, attained by Lin through 2,3-sigmatropic

• very efficient routes to tetracene derivatives containing one or more thiolate (SH) groups for the use in highly electrically conducting organics. In this regard we were attracted by a single result in the early literature [17] showing that traces of allenes related to 2 (X = SCOSMe) were accessible