title: Influence of Ester versus Amide Linkers on the Supramolecular Polymerization Mechanisms of Planar BODIPY Dyes.
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.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.|Institut für Organische Chemie and Center for Nanosystems Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Rödle
authors.affiliation: Institut für Organische Chemie and Center for Nanosystems Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Benedikt
authors.initials: B
authors.lastname: Ritschel
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Mück-Lichtenfeld
authors.affiliation: Institut für Organische Chemie and Center for Nanosystems Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Vladimir
authors.initials: V
authors.lastname: Stepanenko
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany. fernandg@uni-muenster.de.|Institut für Organische Chemie and Center for Nanosystems Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany. fernandg@uni-muenster.de.
authors.forename: Gustavo
authors.initials: G
authors.lastname: Fernández
keywords: BODIPY dyes; cooperativity; non-covalent interactions; self-assembly; supramolecular chemistry