Monocyclic and Dicyclic Dehydro[20]annulenes Integrated with Perylene Diimide

A novel kind of monocyclic and dicyclic dehydro[20]annulenes exhibiting specific sizes and topologies from regioselective unilateral ortho-diethynyl PDI, is developed by Cu-catalyzed Glaser-Hay homo-coupling and cross-coupling. Through the integration of electron-deficient PDI chromophores into the dehydroannulene scaffolding, these macrocycles exhibit intense and characteristic absorption properties and the degenerated LUMO levels. The single-crystal X-ray diffraction analysis unambiguously revealed unique porous supramolecular structures, which display micropore characteristics with surface area of 120.74 m(2) g(-1). A moderate electron mobility of 0.05 cm(2) V-1 s(-1) for chlorine-free dehydro[20]annulene based on micrometer-sized single-crystalline transistors was witnessed. The porous and yet semiconducting features signify the prospects of PDI-integrated dehydroannulenes in organic optoelectronics.

Automated summary

A novel kind of monocyclic and dicyclic dehydro[20]annulenes with specific sizes and topologies are developed through Cu-catalyzed homo-coupling and cross-coupling of regioselective unilateral ortho-diethynyl PDI. The integration of electron-deficient PDI chromophores into the dehydroannulene scaffolding results in intense absorption properties and degenerated LUMO levels. Single-crystal X-ray diffraction analysis reveals unique porous supramolecular structures with micropore characteristics and a surface area of 120.74 m(2) g(-1).