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Journal Article

Vinylene-linked 2D conjugated covalent organic frameworks by Wittig reactions


Feng,  Xinliang       
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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Liu, Y., Fu, S., Pastoetter, D. L., Khan, A. H., Zhang, Y., Dianat, A., et al. (2022). Vinylene-linked 2D conjugated covalent organic frameworks by Wittig reactions. Angewandte Chemie International Edition, 61(49): e202209762. doi:10.1002/anie.202209762.

Cite as: https://hdl.handle.net/21.11116/0000-000B-79A8-0
Vinylene-linked two-dimensional covalent organic frameworks (V-2D-COFs) have shown great promise in electronics and optoelectronics. However, only a few reactions for V-2D-COFs have been developed hitherto. Besides the kinetically low reversibility of C=C bond formation, another underlying issue facing the synthesis of V-2D-COFs is the attainment of high (E)-alkene selectivity to ensure the appropriate symmetry of 2D frameworks. Here, we tailor the E/Z selectivity of the Wittig reaction by employing a proper catalyst (i.e., Cs2CO3) to obtain more stable intermediates and elevating the temperature across the reaction barrier. Subsequently, the Wittig reaction is innovatively utilized for the synthesis of four crystalline V-2D-COFs by combining aldehydes and ylides. Importantly, the efficient conjugation and decent crystallinity of the resultant V-2D-COFs are demonstrated by their high charge carrier mobilities over 10 cm2 V−1 s−1, as revealed by non-contact terahertz (THz) spectroscopy.