Issue 6, 2011

A bio-inspired design strategy: Organization of tryptophan-appended naphthalenediimide into well-defined architectures induced by molecular interactions

Abstract

The chemistry of molecular assemblies involves weak yet complex non-covalent interactions, and the molecular organization of the π-conjugated material is crucial in determining the performance of an organic electronic device. Herein we demonstrate a bioinspired design strategy to tune the self-assembly of naphthalenediimides (NDIs) by minute structural variations, π–π stacking, hydrophobic interactions and metal interactions. We address some of the limitations associated with current design strategies, such as restriction to a specific molecular interaction or the difficulty in controlling the assembly due to several complicated intermolecular interactions. Hydrophobic-effect-induced J-type aggregation and sodium-interaction-induced H-type aggregation of tryptophan-appended NDIs have been illustrated. 1H NMR spectra further reveal sodium cation–π interactions in tryptophan-appended NDIs, while NMR and IR spectroscopic studies confirm the structural variations associated with the molecular assembly. In summary, the molecular organization has been successfully transformed from nanospheres to particles, nanobelts, fibers and fractals. Such drastic changes in the morphology are clear and striking evidence of the importance of non-trivial weak non-covalent forces.

Graphical abstract: A bio-inspired design strategy: Organization of tryptophan-appended naphthalenediimide into well-defined architectures induced by molecular interactions

Supplementary files

Article information

Article type
Paper
Submitted
13 Oct 2010
Accepted
28 Nov 2010
First published
27 Jan 2011

Nanoscale, 2011,3, 2536-2543

A bio-inspired design strategy: Organization of tryptophan-appended naphthalenediimide into well-defined architectures induced by molecular interactions

M. B. Avinash and T. Govindaraju, Nanoscale, 2011, 3, 2536 DOI: 10.1039/C0NR00766H

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