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RESEARCH PRODUCT
Positional Isomers of Chromophore–Peptide Conjugates Self-Assemble into Different Morphologies
Chen LiNellie A. K. OchsWojciech ZajaczkowskiWojciech PisulaWojciech PisulaStefano CorraEiji YashimaSebastian StappertMichal S. ShoshanKlaus MüllenKlaus MüllenUrszula LewandowskaHelma WennemersJunki TanabeJunki Tanabesubject
Models MolecularNanostructurenanostructurepi interactionProtein ConformationNanofibersSupramolecular chemistry02 engineering and technologyImides010402 general chemistry01 natural sciencesCatalysissupramolecular chemistrychemistry.chemical_compoundIsomerismStructural isomerMoietyDirectionalityImidePeryleneChemistryOrganic ChemistryStereoisomerismGeneral Chemistryself-assemblyNanofiberChromophore021001 nanoscience & nanotechnology0104 chemical sciencesCrystallographyPeptideSelf-assemblyPeptides0210 nano-technologyPerylenedescription
Ordering π-systems into defined supramolecular structures is important for the development of organic functional materials. In recent years, peptides with defined secondary structures and/or self-assembly properties were introduced as powerful tools to order peptide-chromophore conjugates into different morphologies. This work explores whether or not the directionality of peptides can be used to control the self-assembly. The position of the π-system in conjugates between oligoprolines and perylene monoimide (PMI) chromophores was varied by attaching the PMI moiety to the second-to-last residue from the C- and N-termini, respectively. Microscopic and diffraction analysis revealed that the positional isomers form distinctly different supramolecular architectures that extend into the micrometer regime. NMR spectroscopic studies in solution phase allowed correlation of the self-assembly properties with markedly different conformational preferences of the isomeric building blocks. These insights enabled the design of building blocks with predictable self-assembly properties. Thus, the directionality of peptides offers exciting opportunities for controlling the self-assembly and electronic properties of π-systems.
year | journal | country | edition | language |
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2018-03-28 |