Liquid crystalline metal-free phthalocyanines designed for charge and exciton transport |
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Authors: | Tant Julien Geerts Yves Henri Lehmann Matthias De Cupere Vinciane Zucchi Gaël Laursen Bo Wegge Bjørnholm Thomas Lemaur Vincent Marcq Valérie Burquel Anick Hennebicq Emmanuelle Gardebien Fabrice Viville Pascal Beljonne David Lazzaroni Roberto Cornil Jérôme |
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Affiliation: | Laboratoire de Chimie des Polymères, Université Libre de Bruxelles, CP 206/1 Boulevard du Triomphe, B-1050 Brussels, Belgium. |
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Abstract: | A joint theoretical and experimental study of the electronic and structural properties of liquid crystalline metal-free phthalocyanines bearing a strong potential for charge and exciton transport has been performed. The synthesis of such compounds has been triggered by quantum chemical calculations showing that: (i) hole transport is favored in metal-free phthalocyanines by their extremely low reorganization energy (0.045 eV) and large electronic splittings; and (ii) the efficiency of energy transfer along the one-dimensional discotic stacks is weakly affected by rotational disorder due to the two-dimensional character of the molecules. We have synthesized two metal-free phthalocyanines with different branched aliphatic chains on the gram scale to allow for a full characterization of their solid-state properties. The two compounds self-organize in liquid crystalline mesophases, as evidenced by optical microscopy, differential scanning calorimetry, X-ray powder diffraction, and molecular dynamics simulations. They exhibit a columnar rectangular mesophase at room temperature and a columnar hexagonal mesophase at elevated temperature. |
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