Co-Crystal Formation of Partially Fluorinated 1,3,5-Tris(phenylethynyl)benzenes |
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Authors: | Dr. Jan-Henrik Weddeling Paul Lukas Waltersmann Beate Neumann Dr. Hans-Georg Stammler Prof. Dr. Norbert W. Mitzel |
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Affiliation: | Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2, Fakultät für Chemie, Universität Bielefeld, Universitätsstraße 25, 33615 Bielefeld, Germany |
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Abstract: | Several rigid 1,3,5-tris(phenylethynyl)benzenes with different fluorination patterns were synthesized through selective Sonogashira-Hagihara coupling reactions to analyze the packing behavior in solid-state structures. The aggregation is dominated by various intermolecular interactions between aryl substituents, triple bonds, C−H bonds and H⋅⋅⋅F contacts. Co-crystallization experiments for the analysis of preferred aryl-aryl-interactions led to 1 : 1 complexes. Intermolecular phenyl-perfluorophenyl interactions with short centroid-centroid distances are dominating these co-crystal structures. They lead to melting point increases of up to 49 °C for the co-crystals compared to the pure substances. |
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Keywords: | 1,3,5-triethynylbenzene crystal engineering halogenated arenes phenyl-perfluorophenyl interactions solid-state structures |
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