Controlled self-assembly triggered by olefin metathesis: cross-linked graphitic nanotubes from an amphiphilic hexa-peri-hexabenzocoronene

Wusong Jin; Takanori Fukushima; Atsuko Kosaka; Makiko Niki; Noriyuki Ishii; Takuzo Aida

doi:10.1021/ja051859p

Controlled self-assembly triggered by olefin metathesis: cross-linked graphitic nanotubes from an amphiphilic hexa-peri-hexabenzocoronene

J Am Chem Soc. 2005 Jun 15;127(23):8284-5. doi: 10.1021/ja051859p.

Authors

Wusong Jin¹, Takanori Fukushima, Atsuko Kosaka, Makiko Niki, Noriyuki Ishii, Takuzo Aida

Affiliation

¹ Aida Nanospace Project, Exploratory Research for Advanced Technology (ERATO), Japan Science and Technology Agency (JST), National Museum of Emerging Science and Innovation, 2-41 Aomi, Koto-ku, Tokyo 135-0064, Japan.

PMID: 15941252
DOI: 10.1021/ja051859p

Abstract

Acyclic diene metathesis (ADMET) in CH2Cl2 of a Gemini-shaped nonionic hexabenzocoronene amphiphile (2), bearing triethylene glycol chains with terminal allylic functionalities, resulted in spontaneous formation of graphitic nanotubes with a cross-linked surface. Without ADMET, 2 did not self-assemble to form a tubular structure due to a high solubility in CH2Cl2. Although 2 formed nanotubes in THF, ADMET on the surface of the preformed nanotubes in THF proceeded only sluggishly and resulted in partial disruption of the tubular structure. The cross-linked nanotubes showed a softening temperature (244 degrees C) higher than that of the uncross-linked version (195 degrees C) and preserved their hollow structure much longer upon heating.