Scalable, Divergent Synthesis of a High Aspect Ratio Carbon Nanobelt

Abstract

Carbon nanobelts are molecules of high fundamental and technological interest due to their structural similarity to carbon nanotubes, of which they are molecular cutouts. Despite this attention, synthetic accessibility is a major obstacle, such that the few known strategies offer limited structural diversity, functionality, and scalability. To address this bottleneck, we have developed a new strategy that utilizes highly fused monomer units constructed via a site-selective [2 + 2 + 2] cycloaddition and a high-yielding zirconocene-mediated macrocyclization to achieve the synthesis of a new carbon nanobelt on large scale with the introduction of functional handles in the penultimate step. This nanobelt represents a diagonal cross section of an armchair carbon nanotube and consequently has a longitudinally extended structure with an aspect ratio of 1.6, the highest of any reported nanobelt. This elongated structure promotes solid-state packing into aligned columns that mimic the parent carbon nanotube and facilitates unprecedented host–guest chemistry with oligo-arylene guests in nonpolar solvents.

Synthesis and Chiral Resolution of Twisted Carbon Nanobelts

“…Nevertheless, the first example of this family, a segment of an armchair [6,6]­CNT, was reported in 2017 . Soon after that, several CNBs with different sizes and edge structures were successfully isolated . In addition, CNBs containing heteroatoms and nonhexagonal rings were also prepared.…”

Latest News: Reactions of Group 4 Bis(trimethylsilyl)acetylene Metallocene Complexes and Applications of the Obtained Products

“…Very recently, Tilley and co‐workers reported a new synthetic strategy for the synthesis of new carbon nanobelts (CNBs). Starting from highly fused monomers and using a site‐selective [2+2+2] cycloaddition with Cp 2 (py)Zr(η 2 ‐Me 3 SiC 2 SiMe 3 ), a high‐yielding macrocyclization was realized on large scale [12c] . The authors concluded that this synthetic method constitutes a general principle for greater synthetic efficiency.…”

Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox

“…1a), which has a cavity shaped like a Celtic cross. The recently revived interest in the synthesis of carbon nanobelts, 11–13 particularly, the efforts to synthesize zigzag carbon nanobelts 14–16 by Diels–Alder reactions 17–20 gave rise to new members of oxanorbornene-fused double-stranded macrocycles, 21 such as 1 17 and 2 20 (Fig. 1a).…”