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Supramolecular naphthalenediimide nanotubes.

Nandhini Ponnuswamy¹, Artur R Stefankiewicz, Jeremy K M Sanders

¹Department of Chemistry, University of Cambridge, Cambridge, UK.

Topics in Current Chemistry

|December 14, 2011

Summary

Amino acid functionalized naphthalenediimides form dynamic libraries in solution. These supramolecular assemblies create nanotubes and hexameric receptors with host-guest properties, influenced by acid-base reactions.

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Materials Science

Background:

Naphthalenediimides (NDIs) are versatile organic molecules.
Dynamic combinatorial libraries (DCLs) offer adaptive molecular systems.
Hydrogen bonding is a key interaction in supramolecular assembly.

Purpose of the Study:

To investigate the self-assembly of amino acid functionalized NDIs in solution.
To explore the host-guest properties of the resulting supramolecular structures.
To understand the influence of guest molecules and acid-base conditions on the assembly.

Main Methods:

Solution-phase self-assembly of NDI derivatives in chloroform.
Characterization of supramolecular structures using spectroscopic and microscopic techniques.

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Investigation of host-guest complexation with C(60), C(70), ion-pairs, and aromatic molecules.

Main Results:

NDIs form dynamic combinatorial libraries stabilized by reversible hydrogen bonds.
Supramolecular nanotubes are formed in chlorinated solvents, capable of complexing various guests.
A hexameric receptor forms in the presence of C(70), with assembly controlled by acid-base reactions.
The "sergeants-and-soldiers" effect is observed when incorporating achiral NDIs into chiral nanotubes.

Conclusions:

Amino acid functionalized NDIs form adaptable supramolecular systems in solution.
The self-assembly leads to nanotubes and hexameric receptors with tunable host-guest capabilities.
These findings open avenues for designing responsive materials and molecular recognition systems.