Synthesis of Nitrogen‐Containing Rubicene and Tetrabenzopentacene Derivatives

Abstract

Carbon-based materials, such as acenes, fullerenes, and graphene nanoribbons, are viewed as the potential successors to silicon in the next generation of electronics. Although a number of methodologies provide access to these materials' all-carbon variants, relatively fewer strategies readily furnish their nitrogen-doped analogues. Herein, we report the rational design, preparation, and characterization of nitrogen-containing rubicenes and tetrabenzopentacenes, which can be viewed either as acene derivatives or as molecular fragments of fullerenes and graphene nanoribbons. The reported findings may prove valuable for the development of electron transporting organic semiconductors and for the eventual construction of larger carbonaceous systems.

(Electro)chemical Oxidation of 6,13‐Bis[tri(isopropyl)silylethynyl]pentacene to its Radical Cation and Dication

“…[17,18] As ac onsequence, however,t his acene andi ts derivatives have been particularly well studied with respectt ot heir structural, chemical, and physical properties. [24] Acene-based devices now indeed demonstrate higherf ield-effect mobilities than those based on amorphous silicon. [24] Acene-based devices now indeed demonstrate higherf ield-effect mobilities than those based on amorphous silicon.…”

“…[10,11] Both the high charge-carrier mobility [10,11] and the HOMO-LUMO gap [19][20][21][22][23] suggest applications for acenes as possible "successors to traditional inorganic semiconductors." [24] Acene-based devices now indeed demonstrate higherf ield-effect mobilities than those based on amorphous silicon. [14] Organic semiconductors provide furthera dvantages over their inorganic counterparts because their properties can be tuned through different molecular structures and functionalization.…”

Efficient Long‐Range Hole Transport Through G‐Quadruplexes

“…to −0.2072 a.u. Similar to the organic polymers with aromatic π‐stacking, the HOMO energy of the entire GQ bridge was enhanced with a larger number of aromatic G‐tetrads integrated into the bridge. Consequently, the energetic barriers at the conjunction of donor–bridge and bridge–acceptor would be reduced, which could facilitate the hole injection to and separation over the bridges and accelerate HT …”

Kationische stickstoffdotierte helikale Nanographene

“…Ein organischer “Bottom‐up”‐Ansatz ermöglicht es, stickstoffdotierte Nanographene mit maßgeschneiderten Strukturen und physikalischen Eigenschaften zu synthetisieren . Während die Synthese von Nanographenen mit pyridinischen– und pyrrolischen– Stickstoffatomen gut untersucht ist, sind kationische stickstoffdotierte Nanographene ( CNDN ) aufgrund anspruchsvollerer Synthesen weniger zugänglich. Bahnbrechende Arbeiten zur Synthese von CNDN s mit planaren Strukturen (Abbildung , links)– zeigten für die erhaltenen Derivate interessante optoelektronische Eigenschaften und supramolekulare Ordnung in Lösung, an der Flüssig‐fest‐Grenzfläche und im Festkörper –.…”