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

Research output: Contribution to journalArticle

25 Citations (Scopus)

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 sp3 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.

Original languageEnglish
Pages (from-to)13196-13199
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number32
DOIs
Publication statusPublished - 2012 Aug 15

Fingerprint

Flavin Mononucleotide
Functional Laterality
Carbon Nanotubes
Single-walled carbon nanotubes (SWCN)
Carbon nanotubes
Conformations
Chirality
Enantioselectivity
Coulomb interactions
Sugars
Nanotubes
Phosphates
DNA
Atoms
Uracil
Static Electricity
Dilatation

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Ju, Sang Yong ; Abanulo, Darlington C. ; Badalucco, Christopher A. ; Gascón, José A. ; Papadimitrakopoulos, Fotios. / Handedness enantioselection of carbon nanotubes using helical assemblies of flavin mononucleotide. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 32. pp. 13196-13199.
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Handedness enantioselection of carbon nanotubes using helical assemblies of flavin mononucleotide. / Ju, Sang Yong; Abanulo, Darlington C.; Badalucco, Christopher A.; Gascón, José A.; Papadimitrakopoulos, Fotios.

In: Journal of the American Chemical Society, Vol. 134, No. 32, 15.08.2012, p. 13196-13199.

Research output: Contribution to journalArticle

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