1. Closed Aromatic Tubes—Capsularenes.
- Author
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Pavlović, Radoslav Z., Zhiquan, Lei, Finnegan, Tyler J., Waudby, Christopher A., Wang, Xiuze, Gunawardana, Vageesha W. Liyana, Zhu, Xingrong, Wong, Curt M., Hamby, Taylor, Moore, Curtis E., Hoefer, Nicole, McComb, David W., Sevov, Christo S., and Badjić, Jovica D.
- Subjects
ELECTRONIC equipment ,X-ray crystallography ,MOLECULAR electronics ,NUCLEAR magnetic resonance spectroscopy ,TUBES ,RING formation (Chemistry) - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2022
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