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Fabrication and Postmodification of Nanoporous Liquid Crystalline Networks via Dynamic Covalent Chemistry Dirk J. Mulder,†,‡ Luc M. W. Scheres,†,§ Jingjin Dong,∥ Giuseppe Portale,∥ Dirk J. Broer,†,⊥ and Albertus P. H. J. Schenning*,†,⊥ †

Department of Functional Organic Materials and Devices, Chemical Engineering and Chemistry, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands ‡ Dutch Polymer Institute (DPI), PO Box 902, 5600 AZ Eindhoven, The Netherlands ∥ Zernike Institute for Advanced Materials, Faculty of Science and Engineering, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands ⊥ Institute for Complex Molecular Systems (ICMS), Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands S Supporting Information *

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1) and a reactive cross-linker (Figure 1a, compound 2) to yield a polymer film that after acid treatment contains reactive pore surface aldehyde functionalities.17 By postmodification of these moieties with a variety of amines, the size and chemical nature of the pores can be tuned in a facile fashion (Figure 1e). The newly developed reactive bisimine 1 was prepared in a two-step synthesis route starting from 4-(6-hydroxyhexyloxy)benzaldehyde. First, a methacrylate ester was prepared, whereafter 1 was obtained from the condensation reaction of the aldehyde with 4-(2-aminethyl)aniline. A methacrylate was used instead of acrylate to prevent side reactions while synthesizing the bisimine. The bisimine based on 4-(2aminethyl)aniline (compound 1) exhibits a smectic phase in a suitable working temperature range (