TY - JOUR

T1 - Resonance structures and aromaticity in capped carbon nanotubes

AU - Graver, Jack E.

AU - Hartung, Elizabeth J.

AU - Williams, Aaron

N1 - Publisher Copyright:
© 2020 Elsevier Ltd

PY - 2021/3

Y1 - 2021/3

N2 - The shape of a single-walled carbon nanotube's cylinder is described by its chiral indices, (n,m), and important properties of the nanotube are determined by this pair of values. In particular, a nanotube is metallic or quasi-metallic when n-m is a multiple of 3, and is otherwise a semiconductor. This paper characterizes the conjugated π-systems that can form on capped nanotubes in each case. When n-m is a multiple of 3, there is a fully conjugated π-system running along the nanotube's cylinder such that two-thirds of the hexagons are benzene rings and one-third are in a resonant set. In contrast, when n-m is not a multiple of 3, the pattern is broken along the length of the cylinder by two fracture lines. Surprisingly, and contrary to conventional thinking, these results are completely independent of the nanotube caps. The results are related to a similar characterization for open nanotubes by Ormsby and King, although in that case only a single fracture line is necessary. This new work is backed by the authors’ previous results on the Clar numbers of fullerenes in general. It also provides new predictions for nanotubes and introduces the concept of the aromaticity ratio.

AB - The shape of a single-walled carbon nanotube's cylinder is described by its chiral indices, (n,m), and important properties of the nanotube are determined by this pair of values. In particular, a nanotube is metallic or quasi-metallic when n-m is a multiple of 3, and is otherwise a semiconductor. This paper characterizes the conjugated π-systems that can form on capped nanotubes in each case. When n-m is a multiple of 3, there is a fully conjugated π-system running along the nanotube's cylinder such that two-thirds of the hexagons are benzene rings and one-third are in a resonant set. In contrast, when n-m is not a multiple of 3, the pattern is broken along the length of the cylinder by two fracture lines. Surprisingly, and contrary to conventional thinking, these results are completely independent of the nanotube caps. The results are related to a similar characterization for open nanotubes by Ormsby and King, although in that case only a single fracture line is necessary. This new work is backed by the authors’ previous results on the Clar numbers of fullerenes in general. It also provides new predictions for nanotubes and introduces the concept of the aromaticity ratio.

KW - Aromaticity

KW - Carbon nanotubes

KW - Clar number

KW - Fullerenes

KW - Kekulé structures

KW - π-systems

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U2 - 10.1016/j.carbon.2020.11.076

DO - 10.1016/j.carbon.2020.11.076

M3 - Article

AN - SCOPUS:85097355331

VL - 173

SP - 1082

EP - 1092

JO - Carbon

JF - Carbon

SN - 0008-6223

ER -