Tuning the LUMO Levels of Z-Shaped Perylene Diimide via Stepwise Cyanation.

The central dogma in constructing organic electron acceptors is to attach electron-withdrawing groups to polycyclic aromatic hydrocarbons. Yet, the full potentials of many organic acceptors were never realized due to synthetic obstacles. By combining the Wittig-Knoevenagel benzannulation, the Pd(0)-catalyzed cyanation, and nucleophilic addition/oxidation cyanation, six polynitrile Z-shaped perylene diimide were synthesized.

Dicyclopenta[ghi,pqr]perylene as a Structural Motif for Bowl-Shaped Hydrocarbons: Synthetic and Conformational Studies.

Dicyclopenta[ghi,pqr]perylene (DCPP) is a substructural fragment on the surface of C yet not on C. Unlike its intensely investigated buckybowl cousins, corannulene and sumanene, DCPP is largely ignored due to the lack of synthetic accessibility. This communication describes the first preparation of a DCPP derivative from bay substituted perylene bis(4-(trifluoromethyl)phenyl)methanol as the key cyclization precursor.

ipso-Cyclization: an emerging tool for multifunctional spirocyclohexadienones.

ipso-Annulation represents an attractive approach to synthesize a variety of spirocyclic compounds having a quaternary carbon center. Furthermore, these compounds also serve as a handy synthon for the construction of various complex molecules. This review presents various useful approaches for the intramolecular ipso-cyclization to afford a wide range of spirocyclohexadienones.

New synthetic routes to Z-shape functionalized perylenes.

Z-shape (1,2,7,8-tetrasubstituted) perylene derivatives are novel chromophores with great potential in various applications. Yet, the synthetic entry into this class of molecules is hitherto quite limited. In this communication, the synthesis of a series of Z-shape perylene derivatives via a double Wittig-Knoevenagel benzannulation protocol is reported.