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Yamamoto T, Fukushima T, Yamamoto Y, Kosaka A, Jin W, Ishii N, Aida T: Stabilization of a kinetically favored nanostructure: surface ROMP of self-assembled conductive nanocoils from a norbornene-appended hexa-peri-hexabenzocoronene. J Am Chem Soc. 2006 Nov 8;128(44):14337-40. Newly designed norbornene-appended hexabenzocoronene 1 self-assembles, upon diffusion of an Et (2) O vapor into its CH (2) Cl (2) solution, to form either graphitic nanocoils or nanotubes, depending on the self-assembling conditions. The coiled assembly, selectively formed at 15 degrees C, is a kinetic intermediate for the tubular assembly and transforms into nanotubes on standing at 25 degrees C. However, post-ring-opening metathesis polymerization of the norbornene pendants of 1 enhances the thermal stability of the coiled assembly as well as the tubular one and disables a thermodynamic coil-to-tube transition. The polymerized nanocoils show an electroconductivity of 1 x 10 (-)(4) S cm (-)(1) upon doping with I (2), while the nonpolymerized nanocoils are disrupted upon being doped. |
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