title: Solvent-Tuned Self-Assembled Nanostructures of Chiral l/d-Phenylalanine Derivatives of Protoporphyrin IX.
abstract: Protoporphyrin IX is a naturally occurring amphiphilic porphyrin with a rigid hydrophobic nonpolar core and two polar propionic acid substitutions on the porphyrin ring. This molecule can be modified on the hydrophilic group, which can lead to strengthened π-π-stacking and spontaneous self-assembly into novel nanostructures. Herein, we use l- phenylalanine and d-phenylalanine to modify protoporphyrin IX, and use the two derivatives for solvophobic-controlled self-assembly. Both derivatives possess two important features: 1) the aromatic core of the porphyrin for dispersive interactions and 2) a chiral amino acid to maximize the influence of chirality on selfassembly. These derivatives lead to the formation of a variety of nanostructure morphologies, such as spheres, nanofibers, lamellar structures, and thread-like and spherical shells. Solution-based self-assembly was determined by UV/Vis, fluorescence, and circular dichroism spectroscopy, and the formed nanostructures were characterized by scanning electron microscopy (SEM). Such engineered porphyrin derivatives could have potential applications in energy transport and storage, supramolecular chemistry, materials science, and medicine.
authors.affiliation: Polymers and Functional Material Division, CSIR-Indian Institute of Chemical Technology Hyderabad, Telangana, 500 007, India ; Department of Organic Chemistry, School of Chemical Sciences, North Maharashtra University Jalgaon, M.S., 425 001, India.
authors.forename: Mr Sharad R
authors.initials: MS
authors.lastname: Bobe
authors.affiliation: School of Applied Sciences, RMIT University GPO Box 2476, Melbourne, VIC, 3001, Australia.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Al Kobaisi
authors.affiliation: School of Applied Sciences, RMIT University GPO Box 2476, Melbourne, VIC, 3001, Australia.
authors.forename: Sheshanath V
authors.initials: SV
authors.lastname: Bhosale
authors.affiliation: Polymers and Functional Material Division, CSIR-Indian Institute of Chemical Technology Hyderabad, Telangana, 500 007, India.
authors.forename: Sidhanath V
authors.initials: SV
authors.lastname: Bhosale
keywords: chiral aggregates; nanostructures; porphyrins; protoporphyrin IX; supramolecular self-assembly