Tri-Petal Lilac-Like Perylene: Asymmetrical Substituted Platform for Regioselective Ether-Exchange Reaction

An asymmetrical tri-petal lilac-like platform based on perylene bisimide (PBI) was designed and synthesized to further perform the ether-exchange reaction, while common tetraphenoxy PBI analogue cannot do it. We found that the tri-petal lilac-like platform strategy not only avoids the regioisomers of difunctionalized PBI, but also is a precise and facile way to achieve regioselective introduction of alkyloxy, alkylthio and C = C double bond ended substituents onto the 1-position of perylene bay without the use and removal of the protecting groups. Due to the tunable photoelectrical properties and functional groups at bay position, these n-type PBI derivatives are promising materials for photovoltaic and supramolecular application.