Synthesis and Characterization of Oligoproline-Based Molecular Assemblies for Light Harvesting

• Published in: Journal of organic chemistry Vol. 71; no. 14; pp. 5186 - 5190
• Main Authors: Aldridge, W. Steven, Hornstein, Brooks J, Serron, Scafford, Dattelbaum, Dana M, Schoonover, Jon R, Meyer, Thomas J
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 07.07.2006
• Subjects: Chemistry; Electrons; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Light; Models, Molecular; Molecular Conformation; Oligopeptides - chemical synthesis; Oligopeptides - chemistry; Oligopeptides - radiation effects; Organic chemistry; Oxidation-Reduction; Peptides; Phenothiazines - chemistry; Photochemistry; Physical chemistry of induced reactions (with radiations, particles and ultrasonics); Preparations and properties; Proline - chemical synthesis; Proline - chemistry; Proline - radiation effects; Purification; Peptides; Nitrogen heterocycle; Metal complex; Electron transfer; Bipyridines; Phenothiazine derivatives; Photochemical reaction; Pyridine derivatives; Characterization; Carboxylic acid; Molecular assembly; Aminoacid; Helical structure; Peptide synthesis; Solid phase; Redox system; Chemical synthesis; Electron donor; Chromophore
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo0603936

Helical oligoproline arrays provide a structurally well-defined environment for building photochemical energy conversion assemblies. The use of solid-phase peptide synthesis (SPPS) to prepare four such arrays, consisting of 16, 17, 18, and 19 amino acid residues, is described here. Each array contains the chromophore [Rub‘2m](PF6)2 (b‘ = 4,4‘-diethylamidocarbonyl-2,2‘-bipyridine; m = 4-methyl-2,2‘-dipyridine-4‘-carboxylic acid) and the electron transfer donor PTZ (phenothiazine). The arrays differ systematically in the distance between the redox-active metal complex and PTZ sites. They have been used in photophysical studies to provide insight into the distance dependence of electron transfer. (J. Am. Chem. Soc. 2004, 126, 14506−14514). This work describes the synthesis, purification, and characterization of the oligoproline arrays, including a general procedure for the synthesis of related arrays.