title: Versatile chiroptics of peptide-induced assemblies of metalloporphyrins.
abstract: Zinc porphyrin functionalized with double long-chain alkylated L-glutamide (GTPP-Zn) was synthesized for the first time, and its self-assembling behaviour was investigated in nonpolar organic solvents. The uniqueness of this functionalized porphyrin is characterized by its drastic colour change from dark green to purple via the formation of chirally stacked structures through selective axial coordination on zinc with pyridine derivatives. In this paper, we report the versatility of the GTPP-Zn assembly process as a stimuli-responsive chiroptical switching system and describe the remarkable ligand-specific induction of secondary chirality accompanied by aggregation morphological change.
authors.affiliation: Department of Applied Chemistry & Biochemistry, Kumamoto University, 2-39-1 Kurokami, Kumamoto, 860-8555, Japan.
authors.forename: Hirokuni
authors.initials: H
authors.lastname: Jintoku
authors.forename: Takashi
authors.initials: T
authors.lastname: Sagawa
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Sawada
authors.forename: Makoto
authors.initials: M
authors.lastname: Takafuji
authors.forename: Hirotaka
authors.initials: H
authors.lastname: Ihara
mesh_terms: D000478:Alkylation; D002942:Circular Dichroism; D003116:Color; D008024:Ligands; D008665:Metalloporphyrins / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D055620:Optical Phenomena; D010455:Peptides / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D012995:Solubility; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D008024:Ligands; D008665:Metalloporphyrins; D010455:Peptides; D011725:Pyridines; D015032:Zinc; C023666:pyridine