Litcius/Paper detail

Azuperylene: The Nonalternant Isomer of Perylene

Siman Liu, Marcos Díaz‐Fernández, Menglin Zhang, Fei Huang, Yong P. Chen, Yudong Yang, José Manuel Marín Beloqui, Jingbo Lan, Jingsong You, Juan Casado, Cheng Zhang

2025Angewandte Chemie International Edition15 citationsDOIOpen Access PDF

Abstract

Abstract The isoelectronic isomer of perylene, hereafter called as azuperylene, has been prepared. Electronic structure analysis reveals that the new isomer can be described as a union of two antiparallel azulenes in which the azulene‐type aromatic character of the starting azulene is partially retained. Four 2,8‐dialkoxy (i.e., ethoxy, n ‐butoxy, n ‐hexyloxy, and n ‐octyloxy) functionalized derivatives of the new isomer core have been prepared. The solid‐state structures of the new compounds have been resolved showing exceptional herringbone π–π stacking ideal for charge transport. Organic field‐effect transistors on sublimated substrates display an excellent hole transport mobility up to 1.03 cm 2 V −1 s −1 that largely surpasses that of perylene and reveals the great potential for charge transport of this new class of nonbenzenoid compounds.

Topics & Concepts

PeryleneAzuleneAntiparallel (mathematics)StackingChemistryAlkoxy groupCharge (physics)Computational chemistryChemical physicsStereochemistryCrystallographyPhotochemistryMoleculeOrganic chemistryPhysicsAlkylMagnetic fieldQuantum mechanicsSynthesis and Properties of Aromatic CompoundsPhotochemistry and Electron Transfer StudiesOrganic Electronics and Photovoltaics