Synthesis, Characterization, and Properties of BN-Fluoranthenes

Abstract

Boron/nitrogen-doped fluoranthenes, a new class of BN-doped cyclopenta-fused polycyclic aromatic hydrocarbons, were synthesized via pyrrolic-type nitrogen directed C−H borylation. Regioselective bromination of BN-fluoranthene (3a) gave mono-and dibrominated BN-fluoranthenes. The halogenated BN-fluoranthene (3b) can undergo various of further crosscoupling reactions to deliver a series of BN-fluoranthenes. Moreover, incorporating BN unit in to fluoranthene resulted in a wider HOMO−LUMO energy gaps. The aromaticities of the BN-fluoranthene (3a) were quantified by experimental and computational studies.

BN-Benzo[b]fluoranthenes: facile synthesis, characterization, and optoelectronic properties

“…Similar results were also observed for other BNdoped PAHs. 11,21 Next, we further calculated the charge distri-Scheme 1 Synthesis of 1 and its solid-state structure. (Hydrogen atoms and solvent molecules are omitted for clarity.…”

“…Among the increasing research on various PAHs, cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs) have been recognized as intriguing π-systems with unique physical and photophysical properties that arise from their non-alternant electronic structures. 8 By taking advantage of the efficient modulation of the electronic structure through the substitution of the CC unit with the B–N unit, a series of BN-doped CP-PAHs with unique optoelectronic properties, such as BN-dibenzo[ a , e ]pentalenes, 9 BN-corannulene, 10 BN-fluoranthene, 11 BN-dibenzo[ a , m ]rubicene, 12 BN-ullazines, 13 etc ., have been developed. Benzo[ b ]fluoranthenes, as one of the representatives of CP-PAHs, which can also be viewed as π-extended fluoranthenes, have been continuously investigated.…”

Transition‐Metal‐Catalyzed 1,2‐Diaminations of Olefins: Synthetic Methodologies and Mechanistic Studies

“…Consequently, much extensive strategic efforts [23–25] have been directed towards the convenient and quick construction of vicinal diamines from the appropriate starting materials. But, from the perspective of drug synthesis, this domain is attractive but still has challenging complications [26–27] in contrast to 1,1‐diaminations [28] …”

“…Especially catalytic, and direct oxidative vicinal diamination/diazidation of olefinic moieties in this scenario has gained substantial research interest in terms of powerful strategies. They represent most convenient, straightforward, efficient, and highly desirable methodologies amongst various reported strategies and still has been of high attraction to synthetic community [4,28] . Moreover, these reports have made significant contribution towards the more rapid drug discovery programme.…”

Synthetic Doping of Acenaphthylene through BN/CC Isosterism and a Direct Comparison with BN-Acenaphthene

“…Cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs), a class of potentially electronically and biologically highly active material, are appealing because of the electronic properties that are associated with the non-alternate PAH ring structures. Despite the blossoming research of “regular” BN-aromatics, composed solely of six-membered rings, BN-doped CP-PAHs have rarely been explored . Acenaphthylene is probably one of the simplest members of the family of CP-PAHs, resembling naphthalene with positions 1 and 8 connected by an ethylene (−CHCH−) unit .…”