Synthesis and Ion Recognition Behavior of Benzo-18-crown-6 Modified Perylene Bisimide

doi:10.7503/cjcu20130350

Abstract

Abstract:

As n-type semiconductor, perylene bisimide and its derivatives have been widely used as liquid crystals, organogels, photoinduced electron transfer systems and organic electronic devices. The construction of supramolecualr assemblies based on the π-π stacking behavior of perylene bisimide has also attracted great interest. As a good acceptor for metal ions, 18-crown-6 has been used in various sensors. To combine the stacking and optoelectronic properties of perylene bisimide with the binding ability of crown ether and obtain a unique sensing behavior, a benzo-18-crown-6 modified perylene bisimide(1) was synthesized. The selectively binding behavior of host 1 toward metal cations and anions were investigated, respectively, using UV-Vis, fluorescence and EPR. Host 1 was found to show a selectively response toward Ba²⁺, which can affect the stacking behavior. Furthermore, host 1 exhibited a selectively response toward F^-, which should be attributed to the anion-π interaction between F^- and the perylene bisimide unit.

Key words: Crown ether, Perylene bisimide, Anion-π interaction, Ion recognition

CLC Number:

O625

TrendMD:

WANG Li-Hua, JIANG Shan, ZHANG Zhi-Jun, ZHANG Heng-Yi, LIU Yu. Synthesis and Ion Recognition Behavior of Benzo-18-crown-6 Modified Perylene Bisimide[J]. Chem. J. Chinese Universities, 2013, 34(9): 2108.

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