Characterisation of the self-assembly of asymmetric functional perylene-based supramolecular polymers Helal Alharbi, Charl F. J Faul University of Bristol, UK Supramolecular polymers (SMPs) are a unique class of materials that are held together by non-covalent and highly directional interactions. Owing to the reversibility of non-covalent interactions, SMPs exhibit significantly more dynamic behaviour, enabling them to display various properties such as self-healing, processability, and stimuli-responsiveness. 1 Perylene diimides (PDIs) have attracted attention as building blocks for SMPs through solution self-assembly. PDIs feature a range of attractive properties, including optoelectronic properties, which enable the investigation of their self-assembly, thermal and photochemical stability, easy chemical modification, and widespread potential applications. 2 Modification of the imide position is one of the strategies for designing novel functional PDIs. 3 Asymmetric PDIs with different substituents at each imide position are an essential subgroup within this class of compounds owing to their substantial synthetic versatility, 4 and have not been explored in great details for their self-assembly behaviour. In this work, we aim to explore the formation of SMPs based on asymmetric PDIs by targeting the imide positions on perylene tetracarboxylic dianhydrides. To facilitate the synthetic process, we applied a recently developed one- step technique developed by Hawker and co-workers, which uses a stoichiometric mixture of various amines in a one-step reaction. 5 Different asymmetric PDIs have been successfully synthesised using a variety of hydrophilic/ hydrophobic amines. We expect to design novel SMPs based on asymmetric PDIs and explore their self- assembly mode, behaviour and resulting supramolecular structures. References 1. T. F. A. De Greef, M. M. J. Smulders, M. Wolffs, A. P. H. J. Schenning, R. P. Sijbesma and E. W. Meijer, Chem. Rev. , 2009, 109 , 5687–5754. 2. C. Jarrett-Wilkins, X. He, H. E. Symons, R. L. Harniman, C. F. J. Faul and I. Manners, Chem. - A Eur. J. , 2018, 24 , 15556– 15565. 3. R. S. Wilson-Kovacs, X. Fang, M. J. L. Hagemann, H. E. Symons and C. F. J. Faul, Chem. – A Eur. J. , 2022, 28 , e202103443. 4. H. Wang, H. Liu, J. Wang, Z. He, Z. Zhang, E. He, R. Zhang and H. Zhang, Tetrahedron , 2016, 72 , 7076–7080. 5. M. J. Robb, B. Newton, B. P. Fors and C. J. Hawker, J. Org. Chem. , 2014, 79 , 6360–6365.
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