Li, ZhiliangZeman, Charles J.Valandro, SilvanoBantang, Jose Paolo O.Schanze, Kirk S.2023-05-262023-05-262023-05-16Molecules 28 (10): 4115 (2023)https://hdl.handle.net/20.500.12588/1867Non-covalent interactions have been extensively used to fabricate nanoscale architectures in supramolecular chemistry. However, the biomimetic self-assembly of diverse nanostructures in aqueous solution with reversibility induced by different important biomolecules remains a challenge. Here, we report the synthesis and aqueous self-assembly of two chiral cationic porphyrins substituted with different types of side chains (branched or linear). Helical H-aggregates are induced by pyrophosphate (PPi) as indicated by circular dichroism (CD) measurement, while J-aggregates are formed with adenosine triphosphate (ATP) for the two porphyrins. By modifying the peripheral side chains from linear to a branched structure, more pronounced H- or J-type aggregation was promoted through the interactions between cationic porphyrins and the biological phosphate ions. Moreover, the phosphate-induced self-assembly of the cationic porphyrins is reversible in the presence of the enzyme alkaline phosphatase (ALP) and repeated addition of phosphates.Attribution 4.0 United Stateshttps://creativecommons.org/licenses/by/4.0/aggregation hydrolysisphosphatesporphyrinsself-assemblyArticle2023-05-26