Synthesis and Self-Assembly of a Discotic Oligo-Carboxylate Tetra-Porphyrin-Perylenebisimide Amphiphile.

ABSTRACT: We report the synthesis of an amphiphilic tetra-porphyrin perylenebisimide (PBI) conjugate via four-fold Suzuki cross-coupling at the PBI ortho-position. Oligo-carboxylate Newkome-type G1 dendrons attached at the porphyrin periphery serve as polar head groups. Theoretical modelling corroborated the assumed planar discotic geometry. The amphiphile is very soluble in mixtures of basic water and THF, where it displays strong aggregation at high water content. Insights into the self-assembly process were obtained by tracking the individualization through THF addition using UV/Vis absorption spectroscopy. Here, a PBI-centred aggregation motif becomes evident. Further evaluation of the morphology via STEM and TEM imaging reveals that the assembly is guided by hydrophobic interactions as well as

SUBMITTER: Schulze EJ 

PROVIDER: S-EPMC12351443 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature