A Straightforward Strategy toward Large BN-Embedded π-Systems: Synthesis, Structure, and Optoelectronic Properties of Extended BN Heterosuperbenzenes

Abstract

A straightforward strategy has been used to construct large BN-embedded π-systems simply from azaacenes. BN heterosuperbenzene derivatives, the largest BN heteroaromatics to date, have been synthesized in three steps. The molecules exhibit curved π-surfaces, showing two different conformations which are self-organized into a sandwich structure and further packed into a π-stacking column. The assembled microribbons exhibit good charge transport properties and photoconductivity, representing an important step toward the optoelectronic applications of BN-embedded aromatics.

Synthesis and Properties of C2h-Symmetric BN-Heteroacenes Tailored through Aromatic Central Cores

“…All of the new compounds were fully characterized by 1 H, 13 C NMR spectroscopy, and high-resolution mass spectrometry. The resonance peaks of the protons in the nitrogen site appear in the aromatic regions (at about 7.8−8.0 ppm, C 2 D 2 Cl 4 , 298 K), suggesting the aromatic nature of these BN-heteroacenes.…”

“…The product should be kept at −20°C in a refrigerator; otherwise, it will be soon decompose to a black solid. mp = 115−117°C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.18 (s, 2H); 13 . In a dry two-necked flask, benzo[1,2-b:4,5-b′]dithiophene-4,8-dione (5.5 g, 25 mmol) was dissolved in freshly distilled THF (150 mL).…”

Ionic liquid immobilization on carbon nanofibers and zeolites: Catalyst design for the liquid-phase toluene chlorination

“…A polarized p-stacking effect could, at least partially, explain this unconventional catalytic behavior. Indeed, a polarized pstacking accounts for a strong polarization of the aromaticlike rings through van der Waals (Keesom) forces induced by the presence of the substituents [16][17][18][19]. Regarding our system, TCCA is a pre-conjugated 6-membered ring and imidazole has the possibility to participate in a normal p-stacking.…”

Contorted polycyclic aromatic hydrocarbons with cove regions and zig-zag edges

“…In the past decade, contorted PAH chemistry has seen remarkable progress (Scheme 1). [11][12][13][14][15][16][17][18][19] For example, as shown in Scheme 1, Nuckolls and coworkers reported the facile synthesis of contorted hexabenzocoronene (c-HBC) and contorted octabenzocircumbiphenyl (c-OBCBs). .…”