The synthesis and structural analysis of perylene 3,4:9,10-tetracarboxylic acid bisimides (PBIs) dendronized with first-generation dendrons are reported. A combination of DSC, X-ray, ED, and solid-state NMR experiments carried out at different temperature on supramolecular columnar structures generated by libraries of (3,4,5)12G1-m-PBI with m=0-4, and (3,4,5)nG1-3-PBI with n=4-14 is reported. Tetramers (m=0, 2-4) and dimers (m=1) of PBI serve as basic repeat units of the supramolecular columns. At high temperature, 2D-hexagonal columnar phases were observed for compounds with n=8-14. At low temperature, 3D orthorhombic or monoclinic columnar array formed via a kinetically controlled process for n=12-14 and a thermodynamically controlled process for n=8-11. Upon annealing, the orthorhombic phase of m=3, n=8-9 transforms into a new thermodynamic product with monoclinic structure through a self-repairing process that optimize the p-stacking structure. This complex helical self-assembly is representative for other classes of dendronlized PBIs of interest for applications in organic electronics and solar cells.

Self-assembly and self-repairing of complex helical columns based on dendronized perylene bisimides

244th National Meeting (2012)

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