Synthesis and fluorescence behavior of 2,5-diphenyl-1,3,4-oxadiazole-containing bismaleimides and bissuccinimides

Abstract

Bismaleimides bearing 2,5-diphenyl-1,3,4-oxadiazole chromophores at para, meta, ortho position and corresponding saturated bissuccinimides were synthesized. Several synthetic strategies for these bismaleimides were discussed in detail. Almost no or very weak fluorescence was observed for these bismaleimides, however, the bissuccinimides show a strong fluorescence. The effect of molecular geometry on optical behavior and fluorescence quenching mechanism were investigated by UV-vis absorption and fluorescence emission spectroscopy. The electron coupling of ground state of p-bismaleimide is stronger than those of m- and o-bismaleimides. p-Bissuccinimide displays increasing fluorescence quantum yields with red shifts of 22–24 nm, compared to m-bissuccinimide. Polymerizable C=C bonds play a key role in the intramolecular fluorescence quenching.

Keywords

fluorescence / bismaleimide / oxadiazole / succinimide

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Acknowledgments

We thank the Alexander von Humboldt Foundation and Mrs. Elisabeth, and Dr. Georg Krohne for their kind help.

Supporting information for this article is available free of charge via the Internet.

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