Perylene with peripherally fused pyrrole and pyridine: columnar packing, anti-Kasha dual emission and reactive oxygen species generation

Simultaneously fusing pyrrole and pyridine at perylene's opposite edges is facilely achieved in this work, yielding PerNN and its various derivatives. All targets demonstrate global diamagnetic ring current. Benefiting from a spatially separated donor-acceptor group within one planar skeleton, PerNN exhibits efficient narrow blue emission and columnar stacking. More importantly, its alkylated derivatives PerNN-MeCl and PerNN-MeI display anti-Kasha dual emission responsive to solvent polarity and reveal highly efficient ROS generation, paving the way to great potential applications. With a spatially separated donor-acceptor group within a plane, PerNN and its derivatives demonstrate properties such as columnar stacking, anti-Kasha dual emission responsive to solvent polarity and efficient ROS generation.