Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 44, Pages 15772-15777Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602592
Keywords
BODIPY dyes; cooperativity; non-covalent interactions; self-assembly; supramolecular chemistry
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Funding
- Alexander von Humboldt Foundation
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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 - 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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