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Title: Closed Aromatic Tubes—Capsularenes
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 baskets47. 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 of4,6and7change 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 capsularenes1(0.7×0.9 nm),8(0.7×1.1 nm;) and9(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.

 
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PAR ID:
10377285
Author(s) / Creator(s):
 ;  ;  ;  ;  ;  ;  ;  ;  ;  ;  ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Angewandte Chemie
Volume:
134
Issue:
41
ISSN:
0044-8249
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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