Issue 6, 2010

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.

Graphical abstract: Versatile chiroptics of peptide-induced assemblies of metalloporphyrins

Supplementary files

Article information

Article type
Paper
Submitted
25 Sep 2009
Accepted
30 Nov 2009
First published
14 Jan 2010

Org. Biomol. Chem., 2010,8, 1344-1350

Versatile chiroptics of peptide-induced assemblies of metalloporphyrins

H. Jintoku, T. Sagawa, T. Sawada, M. Takafuji and H. Ihara, Org. Biomol. Chem., 2010, 8, 1344 DOI: 10.1039/B920058D

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