Handedness enantioselection of carbon nanotubes using helical assemblies of flavin mononucleotide |
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Authors: | Sang-Yong Ju Darlington C Abanulo Christopher A Badalucco José A Gascón Fotios Papadimitrakopoulos |
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Institution: | Nanomaterials Optoelectronics Laboratory (NOEL), Polymer Program, Institute of Materials Science and ?Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269-3136, United States. |
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Abstract: | 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. |
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