A Wavy Two-Dimensional Covalent Organic Framework from Core-Twisted Polycyclic Aromatic Hydrocarbons

Melle-Franco, Manuel; Mart�nez-Abad�a, Marta; Stoppiello, Craig T.; Strutynski, Karol; Lerma-Berlanga, Bel�n; Mart�-Gastaldo, Carlos; Saeki, Akinori; Khlobystov, Andrei N.; Mateo-Alonso, Aurelio

Abstract

A high degree of crystallinity is an essential aspect in two-dimensional covalent organic frameworks, as many properties depend strongly on the structural arrangement of the different layers and their constituents. We introduce herein a new design strategy based on core-twisted polycyclic aromatic hydrocarbon as rigid nodes that give rise to a two-dimensional covalent organic framework with a wavy honeycomb (chairlike) lattice. The concave–convex self-complementarity of the wavy two-dimensional lattice guides the stacking of framework layers into a highly stable and ordered covalent organic framework that allows a full 3D analysis by transmission electron microscopy revealing its chairlike honeycomb facets and aligned mesoporous channels. Remarkably, the waviness of the framework does not disrupt the interlayer π–π stacking that shows charge transporting properties similar to those of planar covalent organic frameworks. The implementation of core-twisted aromatics as building blocks for covalent organic frameworks brings new possibilities in the design of highly ordered organic materials.

Citation

Melle-Franco, M., Martínez-Abadía, M., Stoppiello, C. T., Strutynski, K., Lerma-Berlanga, B., Martí-Gastaldo, C., …Mateo-Alonso, A. (2019). A Wavy Two-Dimensional Covalent Organic Framework from Core-Twisted Polycyclic Aromatic Hydrocarbons. Journal of the American Chemical Society, 141(36), 14403-14410. https://doi.org/10.1021/jacs.9b07383

• Journal Article Type: Article
• Acceptance Date: Aug 20, 2019
• Online Publication Date: Sep 3, 2019
• Publication Date: Sep 11, 2019
• Deposit Date: Sep 9, 2019
• Publicly Available Date: Sep 4, 2020
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Electronic ISSN: 1520-5126
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 141
• Issue: 36
• Pages: 14403-14410
• DOI: https://doi.org/10.1021/jacs.9b07383
• Keywords: Covalent organic frameworks; Polycyclic aromatic hydrocarbons; Twisted aromatics
• Public URL: https://nottingham-repository.worktribe.com/output/2590503
• Publisher URL: https://pubs.acs.org/doi/10.1021/jacs.9b07383
• Additional Information: This material is excerpted from a work that was published in Journal of the American Chemical society , copyright; © American Chemical Society after peer review. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/jacs.9b07383