Pyridine-Fused Azacorannulene: Fine-Tuning of the Structure and Properties of Nitrogen-Embedded Buckybowls

Abstract

Heteroatom-embedded buckybowl molecules provide a fundamental molecular framework that has potential applications in various research fields. However, selective introduction of heteroatoms into buckybowls is challenging, and thus, studies investigating the effect of introduced heteroatoms have been limited. Here, we report the synthesis of pyridine-fused azacorannulene molecules. The influence of nitrogen atoms introduced into the peripheral positions on the structural, electronic, and optical properties is discussed.

1,3‐Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides and Alkynylbenziodoxoles for Synthesis of Functional Dibenzoullazines†

“…In this context, our research group has been actively engaged in the synthesis of functional polycyclic aromatic molecules bearing heteroatoms. [ 20 ] We have developed a novel approach involving the 1,3‐dipolar cycloaddition of polycyclic aromatic azomethine ylides with various dipolarophiles bearing C–C double bonds [ 21‐26 ] and C–C triple bonds, [ 27‐29 ] which effectively yields dibenzoullazine structures. [ 10,18,30‐34 ] As our research progressed, we became intrigued by the potential of alkynyl–iodine(III) reagents as valuable building blocks in organic synthesis.…”

Extended Quinolizinium-Fused Corannulene Derivatives: Synthesis and Properties

“…The most commonly found examples are those with nitrogen atoms at the peripheral positions or within the polycyclic skeleton (Figure ). − …”

Facile Functionalization of Ambipolar, Nitrogen-Doped PAHs toward Highly Efficient TADF OLED Emitters

“…π-Conjugated polycyclic aromatic hydrocarbons (PAHs) − comprising precisely arranged heteroatoms have recently caused a growing interest due to their prospective application in organic electronics. In this context, much attention has been paid to PAH architectures bearing nitrogen atom(s) positioned at the central part (hub position) of aromatic scaffolds (N-PAHs). − The synthetic integration of an N-dopant within three rings (varying from pentagons to heptagons) is anticipated to not only produce a steric constraint that would largely influence the geometry and stability of N-doped PAHs but primarily to affect energy, localization, and spatial extent of a molecular orbital (HOMO) energy level, leading to their strong electron-rich character. , The latter features constitute the development of an innovative class of semiconducting materials that have found utility as organic field effect transistors, sensing, p-type transporting layers in perovskite solar cells, and importantly thermally activated delayed fluorescence (TADF) for organic light-emitting diodes (OLEDs). In this regard, researchers demonstrated nitrogen-embedded PAHs as eligible to cause the multiple resonance (MR) effect in which MOs are alternately distributed likewise to the chess board triggering a short-range charge-transfer (CT) TADF emission.…”