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

Synlett (2017), 28(16), 2121-2125.

Zhou Manxi, Zhu Lei, Sun Zhimin, Yang Zhenqing, Cao Dapeng, Li Qifang

Abstract: An asym. 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 ****og cannot do it. 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 photoelec. properties and functional groups at bay position, these n-type PBI derivs. are promising materials for photovoltaic and supramol. application.