Naphthalenediimide dimers and trimers form self-assembling hydrogen-bonded nanotubes of enhanced stability

Abstract

Covalent linkage of amino acid-functionalised naphthalenediimides (NDIs) produced a dimer and a trimer that form helical, hydrogen-bonded nanotubes in CHCl₃ solutions and that are more resistant than an analogous monomer to the hydrogen-bond disrupting effects of tetrahydrofuran, methanol and heat.

Keywords:

• organic nanotubes
• naphthalenediimide
• dimer
• trimer
• solvophobic

Acknowledgements

The authors are grateful to the National Institutes of Health (R15 GM088748), the Research Corporation for Science Advancement and the Sydney J. Weinberg, Jr Foundation for financial support. NMR spectra were recorded on an instrument purchased with funding from the National Science Foundation (MRI 0922393). CD spectra were recorded at the UCLA DOE Biochemistry Instrumentation Facility, and the authors are grateful to Martin Phillips, the facility's director, for his assistance. Finally, the authors thank G. Dan Pantoş for his invaluable advice on many aspects of the work reported here.