Handedness enantioselection of carbon nanotubes using helical assemblies of flavin mononucleotide.

Sang-Yong Ju, Darlington C Abanulo, Christopher A Badalucco, José A Gascón, Fotios Papadimitrakopoulos

Journal of the American Chemical Society 2012 Aug 15

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In order to truly unlock advanced applications of single-walled carbon nanotubes (SWNTs), one needs to separate them according to both chirality and handedness. Here we show that the chiral D-ribityl phosphate chain of flavin mononucleotide (FMN) induces a right-handed helix that enriches the left-handed SWNTs for all suspended (n,m) species. Such enantioselectivity stems from the sp(3) hybridization of the N atom anchoring the sugar moiety to the flavin ring. This produces two FMN conformations (syn and anti) analogous to DNA. Electrostatic interactions between the neighboring uracil moiety and the 2'-OH group of the side chain provide greater stability to the anti-FMN conformation that leads to a right-handed FMN helix. The right-handed twist that the FMN helix imposes to the underlying nanotube, similar to "Indian burn", causes diameter dilation of only the left-handed SWNTs, whose improved intermolecular interactions with the overlaying FMN helix, impart enantioselection.

Citation

Sang-Yong Ju, Darlington C Abanulo, Christopher A Badalucco, José A Gascón, Fotios Papadimitrakopoulos. Handedness enantioselection of carbon nanotubes using helical assemblies of flavin mononucleotide. Journal of the American Chemical Society. 2012 Aug 15;134(32):13196-9