Pavlovic, Radoslav Z;
Lei, Zhiquan;
Finnegan, Tyler J;
Waudby, Christopher A;
Wang, Xiuze;
Gunawardana, Vageesha W Liyana;
Zhu, Xingrong;
... Badjic, Jovica D; + view all
(2022)
Closed Aromatic Tubes-Capsularenes.
Angewandte Chemie International Edition
, 61
(41)
, Article e202211304. 10.1002/anie.202211304.
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Abstract
In this study, we describe a synthetic method for incorporating arenes into closed tubes that we name capsularenes. First, we prepared vase-shaped molecular baskets 4–7. The baskets comprise a benzene base fused to three bicycle[2.2.1]heptane rings that extend into phthalimide (4), naphthalimide (6), and anthraceneimide sides (7), each carrying a dimethoxyethane acetal group. In the presence of catalytic trifluoroacetic acid (TFA), the acetals at top of 4, 6 and 7 change into aliphatic aldehydes followed by their intramolecular cyclization into 1,3,5-trioxane (1H NMR spectroscopy). Such ring closure is nearly a quantitative process that furnishes differently sized capsularenes 1 (0.7×0.9 nm), 8 (0.7×1.1 nm;) and 9 (0.7×1.4 nm;) characterized by X-Ray crystallography, microcrystal electron diffraction, UV/Vis, fluorescence, cyclic voltammetry, and thermogravimetry. With exceptional rigidity, unique topology, great thermal stability, and perhaps tuneable optoelectronic characteristics, capsularenes hold promise for the construction of novel organic electronic devices.
| Type: | Article |
|---|---|
| Title: | Closed Aromatic Tubes-Capsularenes |
| Location: | Germany |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/anie.202211304 |
| Publisher version: | https://doi.org/10.1002/anie.202211304 |
| Language: | English |
| Additional information: | This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is noncommercial and no modifications or adaptations are made. |
| Keywords: | Science & Technology, Physical Sciences, Chemistry, Multidisciplinary, Chemistry, Acenes, Aromatic Compounds, Molecular Electronics, Supramolecular Catalysis, Trioxanes, DIASTEREOSELECTIVE SYNTHESIS, SUPRAMOLECULAR CATALYSIS, CARBON NANOTUBES, MACROCYCLES, STARANDS, ENERGY, CYCLOTRIMERIZATION, ORTHOCYCLOPHANES, PERSPECTIVES, PROTONATION |
| UCL classification: | UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10156850 |
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