Novel Synthetic Approach to Heteroatom Doped Polycyclic Aromatic Hydrocarbons: Optimizing the Bottom-Up Approach to Atomically Precise Doped Nanographenes

Abstract

The success of the rational bottom-up approach to nanostructured carbon materials and the discovery of the importance of their doping with heteroatoms puts under the spotlight all synthetic organic approaches to polycyclic aromatic hydrocarbons. The construction of atomically precise heteroatom doped nanographenes has evidenced the importance of controlling its geometry and the position of the doping heteroatoms, since these parameters influence their chemical–physical properties and their applications. The growing interest towards this research topic is testified by the large number of works published in this area, which have transformed a once “fundamental research” into applied research at the cutting edge of technology. This review analyzes the most recent synthetic approaches to this class of compounds.

Atomically Precise Distorted Nanographenes: The Effect of Different Edge Functionalization on the Photophysical Properties down to the Femtosecond Scale

“…Instead, moving from c-NG to c-Br-NG, we found a much more marked variation, determining a deep alteration of the excited state relaxation dynamics, as highlighted by the pulse-limited decay of the PL band and the concurrent transition to another emitting state. By a direct comparison of the structures of c-NG and c-Br-NG , we can directly ascribe such a behavior to the introduction of the two bromine atoms favoring a heavy atom effect [ 40 , 41 ]. The resulting enhancement of the spin–orbit coupling thus determines an increase in the intersystem crossing rate from singlet state S 1 to triplet state T 1 .…”

Collective Quantum Magnetism in Nitrogen-Doped Nanographenes

“…The introduction of rich and excellent chemical reactivity by heteroatom substitution provides a flexible toolbox for the fabrication of complex graphene nanostructures which may be retractable by using molecular precursors with pure carbons. Complex covalent single molecules, one-dimensional chains, and even two-dimensional networks with nitrogen substitutions have been fabricated on surfaces. ,,,,− Bearing efficient and selective coupling reactions and the ability to tune electronic properties, heteroatom doping provides a promising route to realize ordered quantum phases in extended nanographene networks, which remains a formidable challenge in the field of carbon quantum magnetism.…”

Boron‐ and nitrogen‐embedded blue multi‐resonance emitters with low triplet energy

“…Embedding multiple heteroatoms into polycyclic aromatic hydrocarbons (PAHs) has garnered significant attention in the fields of optoelectronics and organic semiconductors. [1][2][3][4][5][6] For example, the inclusion of boron and nitrogen atoms into PAHs allows the manipulation of their optoelectronic properties through modifications of their orbital interactions. [7][8][9] This material, which so called azaborine, exhibits an intriguing resonance effect because of electron-accepting and electron-donating nature of B and N atoms, respectively, and effective localization of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) on distinct carbon atoms.…”