Bowl-Shaped Naphthalimide-Annulated Corannulene as Nonfullerene Acceptor in Organic Solar Cells

Abstract

An electron-poor bowl-shaped naphthalimide-annulated corannulene with branched alkyl residues in the imide position was synthesized by a palladium-catalyzed cross-coupling annulation sequence. This dipolar compound exhibits strong absorption in the visible range along with a low-lying LUMO level at –3.85 eV, enabling n-type charge transport in organic thin-film transistors. Furthermore, we processed inverted bulk-heterojunction solar cells in combination with the two donor polymers PCE–10 and PM6 to achieve open-circuit voltages up to 1.04 V. By using a blend of the self-assembled naphthalimide-annulated corannulene and PCE–10, we were able to obtain a power conversion efficiency of up to 2.1%, which is to the best of our knowledge the highest reported value for a corannulene-based organic solar cell to date.

Effect of Fusion Manner of Concave Molecules on the Properties of Resulting Nanoboats

“…Corannulene and sumanene represent the simplest buckybowls, which can be viewed as the fragments mapped from fullerene and have been widely studied . Further functionalization of these compounds with some special functional groups can generate surface-extended aromatic hydrocarbons with distinctive geometries, fascinating characteristics, and potential applications in fields of supramolecular chemistry and material sciences . Additionally, larger buckybowls that are mapped from C 70 or higher fullerenes have also been reported …”

One-step synthesis of polycyclic thianthrenes from unfunctionalized aromatics by thia-APEX reactions

“…In addition, the columnar packing structure of thianthrene 3ea is the first example of mono-benzodithiine-fused corannulene, 3,7 e whereas there are a lot of other rim -region-fused or rim -region-substituted corannulene derivatives showing a similar columnar stacking ability. 25 We expect that the columnar stacking achieved by the simple structural motif of benzodithiinocorannulene can provide a fruitful insight into the application of corannulene-based functional materials in organic electronics 26 and supramolecular chemistry 27 as well as host–guest chemistry. 3…”

Naphthalimide-Annulated [n]Helicenes: Red Circularly Polarized Light Emitters

“…In conclusion, two naphthalimide-annulated [ n ]­helicenes 1 and 2 were synthesized through a twofold palladium-catalyzed [3 + 3] annulation reaction in high yields. These compounds enrich the family of so far existing annulation products between naphthalimide units and various polycyclic aromatic cores as given in extended planar or core-twisted higher rylene bisimides and bowl-shaped corannulene bisimides or zethrene bisimides by annulation products bearing chiral aromatic helicene interconnectors. The structure of the new molecules was unambiguously proven by single-crystal X-ray diffraction analysis of enantiopure fractions of 1 and 2 obtained by chiral HPLC, and the absolute configuration of the enantiopure fractions was assigned by X-ray structure analysis and comparison of measured and computed CD spectra.…”