BN Heterosuperbenzenes: Synthesis and Properties

Abstract

Replacement of C=C unit with its isoelectronic B-N unit in aromatics provides a new class of molecules with appealing properties, which have attracted great attention recently. In this Concept, we focus on BN-substituted polycyclic aromatics with fused structures, and review their synthesis, photophysical, and redox properties, as well as their applications in organic electronics. We also present challenging synthetic targets, large BN- substituted polycyclic aromatics, such as regioregular BN heterosuperbenzenes, which can be viewed as BN-doped nanographenes. Finally, we propose an atomically precise bottom-up synthesis of structurally well-defined BN-doped graphenes.

New advances in nanographene chemistry

“…[139][140][141] The dipolar BN unit has a significant impact on the molecular orbitals, intermolecular interactions and photophysical and redox properties of the p-system, providing a unique strategy for molecular engineering. [139][140][141] The dipolar BN unit has a significant impact on the molecular orbitals, intermolecular interactions and photophysical and redox properties of the p-system, providing a unique strategy for molecular engineering.…”

“…[139][140][141] The dipolar BN unit has a significant impact on the molecular orbitals, intermolecular interactions and photophysical and redox properties of the p-system, providing a unique strategy for molecular engineering. 139 Here we mainly focus on large BN-embedded p-skeletons, which are model compounds and potential precursors for BN-doped graphenes. 139 Here we mainly focus on large BN-embedded p-skeletons, which are model compounds and potential precursors for BN-doped graphenes.…”

Recent Developments in Azaborinine Chemistry

“…BN‐containing extended structures (mostly within fused rings) in the context of material chemistry have recently been reviewed. [24b], [24c]…”

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

“…By exploiting organic synthetic tools,21, 22 one can tune the molecular HOMO–LUMO gap8 by 1) changing the size and edge of the carbon‐based aromatic framework; 2) varying the molecular planarity upon insertion of bulky substituents or bridging chains; 3) changing the aromatic properties of the constituent monomeric units; 4) varying the peripheral functionalization through the insertion of electron‐donating or electron‐ withdrawing substituents; 5) enclosing structural defects; 6) promoting supramolecular interactions between individual molecules governing their organization into a condensed phase, and 7) replacing selected carbon atoms by isostructural and isoelectronic analogues (i.e., doping). In particular, the heteroatom‐doping approach23, 24 is increasingly becoming important, as significant perturbation of the optoelectronic properties can be obtained without a substantial structural modification 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36…”