NDLI: Solvent-Induced Helical Assembly and Reversible Chiroptical Switching of Chiral Cyclic-Dipeptide-Functionalized Naphthalenediimides

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Solvent-Induced Helical Assembly and Reversible Chiroptical Switching of Chiral Cyclic-Dipeptide-Functionalized Naphthalenediimides

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Prathyusha, V. Govindaraju, T. Manchineella, Shivaprasad Priyakumar, U. Deva
Description	Author Affiliation: Manchineella S ( Bioorganic Chemistry Laboratory, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore 560064 (India), Fax: (+91) 80-2208-2627.)
Abstract	Understanding the roles of various parameters in orchestrating the preferential chiral molecular organization in supramolecular self-assembly processes is of great significance in designing novel molecular functional systems. Cyclic dipeptide (CDP) chiral auxiliary-functionalized naphthalenediimides (NCDPs 1–6) have been prepared and their chiral self-assembly properties have been investigated. Detailed photophysical and circular dichroism (CD) studies have unveiled the crucial role of the solvent in the chiral aggregation of these NCDPs. NCDPs 1–3 form supramolecular helical assemblies and exhibit remarkable chiroptical switching behaviour (M- to P-type) depending on the solvent composition of HFIP and DMSO. The strong influence of solvent composition on the supramolecular chirality of NCDPs has been further corroborated by concentration and solid-state thin-film CD studies. The chiroptical switching between supramolecular aggregates of opposite helicity (M and P) has been found to be reversible, and can be achieved through cycles of solvent removal and redissolution in solvent mixtures of specific composition. The control molecular systems (NCDPs 4–6), with an achiral or D-isomer second amino acid in the CDP auxiliary, did not show chiral aggregation properties. The substantial roles of hydrogen bonding and π–π interactions in the assembly of the NCDPs have been validated through nuclear magnetic resonance (NMR), photophysical, and computational studies. Quantum chemical calculations at the ab initio, semiempirical, and density functional theory levels have been performed on model systems to understand the stabilities of the right (P-) and left (M-) handed helical supramolecular assemblies and the nature of the intermolecular interactions. This study emphasizes the role of CDP chiral auxiliaries on the solvent-induced helical assembly and reversible chiroptical switching of naphthalenediimides.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	49
Volume Number	19
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2013-12-02
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Dipeptides Chemistry Imides Naphthalenes Peptides, Cyclic Circular Dichroism Models, Molecular Protein Structure, Secondary Solvents Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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