Title: A Bottom-Up Construction of Nanotube Materials From Renewable Resources
Author: Mitsutoshi Masuda
Last saved by: James B. Lewis
Company: NIMC

A Bottom-Up Construction of Organic Nanotubes From Renewable Resources

George John,^a Mitsutoshi Masuda,^a,b  Kiyoshi Yase,^c and Toshimi Shimizu ^a,b

^aCREST, Japan Science and Technology Corporation (JST), NARC, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 4, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8562, Japan. TEL: +81-298-61-2688; FAX: +81-298-61-2659; E-Mail: george-john@aist.go.jp
^bNanoarchitectonics Research Center (NARC), AIST, Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan.
^cPhotonics Research Institute, AIST, Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan.

The self-assembly of low molecular weight building blocks into noncovalent polymeric nanostructures has recently attracted considerable interest for applications in nanotechnology as a bottom-up approach for the construction of molecular-scale devices [1]. The building blocks currently used in supramolecular chemistry are synthesized mainly from petroleum-based starting materials. However, bio-based organic synthesis presents distinct advantages for the generation of new building blocks since (a) they are obtainable from renewable resources; (b) they are likely to be biodegradable; (c) natural compounds have a wealth of structural diversity that has yet to be explored. This study is an effort to combine the philosophies of green chemistry and supramolecular chemistry, making use of renewable plant-derived resources as the starting materials (an alternate feedstock) for the noncovalent synthesis of meso- and nanoscale structures. The use of cardanol (obtained from Anacardium occidentale L, a renewable resource and a by-product of the cashew industry) and its derivatives for various applications is well known. However, its use in the synthesis of aryl glycolipids and their self-assembled nanostructures are described here for the first time. Simple glycolipids derived from cardanol were self-assembled in water initially form helical coiled nanofibers and then gradually turn into tubular structures of several tens to several hundreds of micrometers long and internal diameters of 10-15 nm (Figure 1). The nanotubes are found to be open ended, with uniform shape and internal diameter with a wall consisting of two to four lipid interdigitated bilayers.

[1]. G. John, M. Masuda, Y. Okada, K. Yase, T. Shimizu, Adv. Mat., 13, 715 (2001).