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

Abstract

Oxanorbornene-fused double-stranded macrocycles, represented by kohnkene, are not only synthetic precursors toward short segments of zigzag carbon nanotubes but also typical cavitands processing an intrinsic cavity. However, their capability to bind guest molecules in solution remained unexplored. Herein we report a new member of oxanorbornene-fused double-stranded macrocycles, which is named a nanobox herein because of its shape. Reductive aromatization of this oxanorbornene-fused nanobox leads to observation of a new zigzag carbon nanobelt by high resolution mass spectroscopy. The fluorescence titration and NMR experiments indicate that this nanobox encapsulates C70 in solution with a binding constant of (3.2 ± 0.1) × 106 M−1 in toluene and a high selectivity against C60 and its derivatives. As found from the X-ray crystallographic analysis, this nanobox changes the shape of its cross-section from a rhombus to nearly a square upon accommodating C60.

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

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Article information

Article type
Edge Article
Submitted
24 Nov 2021
Accepted
12 Jan 2022
First published
13 Jan 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022, Advance Article

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

H. Chen, Z. Xia and Q. Miao, Chem. Sci., 2022, Advance Article , DOI: 10.1039/D1SC06553J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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