Synthesis and Aggregation of Amphiphilic Porphyrin-Perylenebisimide Dyads

Schulze E, Wu M, Methfessel C, Spiecker E, Hirsch A (2025)

Publication Type: Journal article

Publication year: 2025

Journal

DOI: 10.1002/chem.202500279

Abstract

We report the straightforward synthesis of a family of amphiphilic zinc-porphyrin-perylenebisimide (PBI) dyads containing sterically demanding substituents at the porphyrin meso-position, as well as at the PBI bay-position. The hydrophilic head group consists of oligo-carboxylic acid G2-Newkome dendrons attached to the porphyrin, whereas lipophilic pentyl-hexyl-swallowtails are connected to the PBI imide position. Using UV/Vis absorption and fluorescence emission spectroscopy, their tetrahydrofuran (THF) initiated disaggregation was studied in aqueous media. Without meso-substituents, a stronger interaction between the porphyrins was observed in the aggregated state. Insights into the size and morphology of the aggregates were obtained by dynamic light scattering (DLS) and scanning transmission electron microscopy (STEM). Supported by density functional theory (DFT) calculations, these revealed micelles and liposomes as plausible architectures.

Authors with CRIS profile

Erik Schulze Lehrstuhl für Organische Chemie II Mingjian Wu Lehrstuhl für Werkstoffwissenschaften (Mikro- und Nanostrukturforschung) Christian Methfessel Lehrstuhl für Organische Chemie II Erdmann Spiecker Lehrstuhl für Werkstoffwissenschaften (Mikro- und Nanostrukturforschung) Andreas Hirsch Lehrstuhl für Organische Chemie II

How to cite

APA:

Schulze, E., Wu, M., Methfessel, C., Spiecker, E., & Hirsch, A. (2025). Synthesis and Aggregation of Amphiphilic Porphyrin-Perylenebisimide Dyads. Chemistry - A European Journal. https://doi.org/10.1002/chem.202500279

MLA:

Schulze, Erik, et al. "Synthesis and Aggregation of Amphiphilic Porphyrin-Perylenebisimide Dyads." Chemistry - A European Journal (2025).

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