Fused polycyclic aromatics incorporating boron in the core: fundamentals and applications

Abstract

The incorporation of boron into the core structure of fused polycyclic aromatics generates compounds with highly attractive properties that have recently received significant attention. Embedding boron into the backbone of ladder or 2D poly aromatic hydrocarbons is an underexplored approach to modulate optoelectronic properties, with tricoordinate boron representing a novel acceptor moiety for organic optoelectronic applications. Furthermore, the incorporation of boron into polycyclics containing other heteroatoms (e.g., chalcogens or pnictogens) leads to more extensive structural diversity and considerable ability to modify the frontier orbital energies and character, often in a controlled manner, to fine tune material properties for specific applications. This feature article summarizes the recent key developments in this field.

New advances in nanographene chemistry

“…167 However, the steric bulkiness prevents intermolecular interactions in the solid state, which is detrimental to charge transport properties. Generally, B-containing compounds are unstable toward moisture and oxygen owing to the intrinsic high reactivity of B atoms.…”

Expedient Synthesis of 1,2‐Thiaborines by Means of Sulfur Insertion into Boroles

“…Recently, there have been significant advances in the development of benzene analogues that feature a boron atom with an adjacent lone‐pair bearing atom, effectively acting as a C=C substitute in novel heteroarene systems . In particular, this chemistry has flourished for boron/nitrogen species, namely 1,2‐azaborines ( A , Figure ) .…”

“…Recently,t here have been significant advances in the development of benzene analogues that feature ab oron atom with an adjacent lone-pair bearinga tom, effectively acting as aC =C substitute in novel heteroarene systems. [1][2][3][4] In particular, this chemistry has flourished for boron/nitrogen species, namely 1,2-azaborines (A,F igure 1). [5][6][7][8][9][10][11] With respectt ob oron-oxygen analogues (1,2-oxaborines, B), numerousf used polycyclic systems are known, as well as five monocyclic species.…”

Azaindolo[3,2,1‐jk]carbazoles: New Building Blocks for Functional Organic Materials

“…The concept of heteroatom doping is widely employed in silicon‐based semiconductor technology. Analogously, the incorporation of heteroatoms into polycyclic aromatic scaffolds has been demonstrated to effectively modify the photophysical and electrochemical properties of the parent material . In particular, nitrogen incorporation into acenes has been successfully realized to induce n‐type charge‐transport properties in materials for OFET applications .…”