Ordered nanoporous scaffolds via self-assembling organic building blocks

ORGN 375

Trent H. Galow, trent.galow@ed.ac.uk1, Andrew D. Stretton1, Ifor D. W. Samuel, idws@st-andrews.ac.uk2, and Olivier P. M. Gaudin2. (1) School of Chemistry, University of Edinburgh, Edinburgh, United Kingdom, (2) Organic Semiconductor Centre, University of St. Andrews, St. Andrews, United Kingdom
Multipurpose, ordered nanoporous thin films have been generated on a variety of surfaces by utilizing the self-organising capabilities of supramolecular discotic liquid crystals and the reversibility of hydrogen bonding interactions. Possible applications include real-time electrochemical sensors, solar cells, miniaturised hard disks, and drug delivery devices. A D3h symmetric discotic H-bonding complex 1.2 was designed and prepared consisting of a benzotri(imidazole) core 2 bound to three complementary methacrylate-derived gallic acid units 1. Spin coated films of the discotic mesogen cooled gradually from the isotropic phase, show hexagonal dendritic patterns under crossed polarisers arising from homeotropic or ‘face-on' alignment. Rigid cross-linked films were created by photopolymerisation of the methacrylate units. Etching of the benzotri(imidazole) cores in a polar solvent afforded an ordered nanoporous scaffold with hexagonally-close packed pores.