Web Release Date: January 11,
Radially Diblock Nanotube: Site-Selective Functionalization of a Tubularly Assembled Hexabenzocoronene
and
ERATO-SORST Nanospace Project, Japan Science and Technology Agency (JST), National Museum of Emerging Science and Innovation, 2-41 Aomi, Koto-ku, Tokyo 135-0064, Japan, Department of Chemistry and Biotechnology, School of Engineering, and Center for NanoBio Integration, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan, and Biological Information Research Center, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central-6, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8566, Japan
Received August 3, 2007
Abstract:
An amphiphilic Gemini-shaped hexa-peri-hexabenzocoronene (1) with azide functionalities self-assembles to form graphitic nanotubes whose interior and exterior surfaces can be post-functionalized by "click chemistry". A click reaction of the nanotubes with bulky macromolecules such as a dendronized alkyne (G2-alkyne) takes place site-selectively on the exterior surface of the nanotubes, leaving the azide functionalities on the interior surface mostly intact. A subsequent click reaction of the resulting nanotubes with alkynes having a much smaller steric bulk allows the remaining azide groups to be functionalized, affording radially diblock graphitic nanotubes.
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