Closed Aromatic Tubes—Capsularenes. (6th September 2022)

• Record Type: Journal Article
• Authors: 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.; Badjić, Jovica D.
• Is Part Of: Angewandte Chemie. Volume 134:Number 41(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-06
• Subjects: Acenes -- Aromatic Compounds -- Molecular Electronics -- Supramolecular Catalysis -- Trioxanes; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202211304
• Languages: English
• ISSNs: 0044-8249

Abstract

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 ( 1 H 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 : Arenes can now be incorporated into closed tubes—capsularenes. These rigid, electron deficient, thermally stable, and tubular molecules with three arenes or acenes at a close distance can lend themselves to the construction of organic electronic devices.