Construction of well-defined butadiynylene-linked perylene bisimide arrays via cross-coupling

A homogeneous series of well-defined oligo-butadiynylene-PBIs have been efficiently synthesized in one pot by Hay Cross-Coupling. It is shocked that the rate of this oxidative coupling reaction is very fast, the whole process just takes a short time no more than 10 s. The four butadiynylene-linked oligomers having good solubility in common solvents show absorption spectra with broad absorption range (from 300 nm to 650 nm) and gradually increasing absorption coefficients (up to 1.4 × 105 mol−1 cm−1). From the cyclic voltammentry data, we can see that the LUMO levels are effectively and precisely tuned by embedding butadiynylene linkage between PBI subunits. These compounds are promising for potential applications in molecular electronic devices such as conducting molecular wires and solar cells.

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► A series of oligo-butadiynylene-PBIs were synthesized by Hay Coupling within 10 s.
► These oligomers have broad absorption spectra with high extinction coefficients.
►  The LUMO levels of these oligomers are effectively and precisely tuned.
► These oligomers up to five PBI units are promising for use in molecular devices.