Influence of Ester versus Amide Linkers on the Supramolecular Polymerization Mechanisms of Planar BODIPY Dyes |
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Authors: | Alexander Rödle Benedikt Ritschel Dr Christian Mück‐Lichtenfeld Dr Vladimir Stepanenko Prof Dr Gustavo Fernández |
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Institution: | 1. Organisch-Chemisches Institut, Westf?lische Wilhelms-Universit?t Münster, Münster, Germany;2. Institut für Organische Chemie and Center for Nanosystems Chemistry, Julius-Maximilians-Universit?t Würzburg, Würzburg, Germany |
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Abstract: | We report the H‐type supramolecular polymerization of two new hydrophobic BODIPY derivatives equipped with ester and amide linkages. Whereas the ester‐containing BODIPY derivative undergoes an isodesmic supramolecular polymerization in which the monomers are parallel‐oriented, the replacement of the ester by amide groups leads to a highly cooperative self‐assembly process into H‐type aggregates with a rotational displacement of the dye molecules within the stack. The dye organization imposed by simultaneous π–π and hydrogen bonding interactions is the driving force for the cooperative supramolecular polymerization, whereas the absence of additional hydrogen bonds for the ester‐containing moiety does not suffice to induce cooperative phenomena. |
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Keywords: | BODIPY dyes cooperativity non-covalent interactions self-assembly supramolecular chemistry |
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