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Issue 31, 2020
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Tubularenes

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Abstract

We report the synthesis and characterization of conjugated, conformationally rigid, and electroactive carbon-based nanotubes that we term tubularenes. These structures are constructed from a resorcin[nb]arene base. Cyclization of the conjugated aromatic nanotube is achieved in one-pot eight-fold C–C bond formation via Suzuki–Miyaura cross-coupling. DFT calculations indicate a buildup of strain energy in excess of 90 kcal mol−1. The resulting architectures contain large internal void spaces >260 Å3, are fluorescent, and able to accept up to 4 electrons. This represents the first scaffolding approach that provides conjugated nanotube architectures.

Graphical abstract: Tubularenes

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Supplementary files

Article information


Submitted
18 Jun 2020
Accepted
13 Jul 2020
First published
14 Jul 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 8089-8094
Article type
Edge Article

Tubularenes

S. Mirzaei, E. Castro and R. H. Sánchez, Chem. Sci., 2020, 11, 8089
DOI: 10.1039/D0SC03384G

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