The
development of a facile method to sort semiconducting single-walled
carbon nanotubes (s-SWCNTs) and their enantiomer recognition are still
great challenges. We here describe a finding that a commercially available,
safe, and cost-effective hydrophobic riboflavin analogue (riboflavin
tetrabutyrate; RTB) efficiently sorts only s-SWCNTs by
a one-pot method (bath-type sonication for 30 min followed by ultracentrifugation)
and recognizes their enantiomers (left- and right-handed s-SWCNTs).
The solubilization behavior of the SWCNTs strongly depends on the
concentration of RTB; namely, with the decrease in the
concentration of RTB, the s-SWCNT (n,m)-chiral selective sorting efficiency is enhanced.
When using RTB = ∼0.4 mM (SWCNTs = 1 mg/3 mL toluene),
two (n,m) chiralities of the s-SWCNTs
with (n,m) = (8,6) and (8,7) were
efficiently sorted. Furthermore, when using RTB = 0.5–1
mM, the SWCNT enantiomer recognition was observed. In addition, the
X-ray photoelectron spectroscopic study revealed that the adsorbed RTB molecules on the s-SWCNTs were readily removed by simple
rinsing with acetone to provide adsorbent-free pure s-SWCNTs. On the
basis of the experimentally obtained data using Raman, photoluminescence,
and visible–near-IR absorption spectroscopy techniques and
computational density functional theory (DFT) approaches, we have
revealed a possible mechanism for this unique s-SWCNT selective sorting
and their enantiomer recognition. The supramolecular orientation of RTB into the helical superlattice with its own chirality provides
a mechanism for chirality recognition. The study demonstrates one-pot
sorting of s-SWCNTs and their enantiomer recognition using a cost-effective,
safe molecule. Such a study is important for s-SWCNT separation science
and its application in nanoscience and engineering areas.