Imperial College London
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Professor David W. McComb

Faculty of Engineering, Department of Materials

Adjunct Professor
 
 
 
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Contact

 

+44 (0)20 7594 6750d.mccomb Website

 
 
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Location

 

Royal School of MinesSouth Kensington Campus

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Summary

 

Publications

Citation

BibTex format

@article{Pavlović:2022:10.1002/anie.202211304,
author = {Pavlovi, RZ and Zhiquan, L and Finnegan, TJ and Waudby, CA and Wang, X and Gunawardana, VWL and Zhu, X and Wong, CM and Hamby, T and Moore, CE and Hoefer, N and McComb, DW and Sevov, CS and Badji, JD},
doi = {10.1002/anie.202211304},
journal = {Angew Chem Int Ed Engl},
title = {Closed Aromatic Tubes-Capsularenes.},
url = {http://dx.doi.org/10.1002/anie.202211304},
volume = {61},
year = {2022}
}
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RIS format (EndNote, RefMan)

TY  - JOUR
AB  - 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 (0.7×0.9nm), 8 (0.7×1.1nm;) and 9 (0.7×1.4nm;) 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.
AU  - Pavlovi,RZ
AU  - Zhiquan,L
AU  - Finnegan,TJ
AU  - Waudby,CA
AU  - Wang,X
AU  - Gunawardana,VWL
AU  - Zhu,X
AU  - Wong,CM
AU  - Hamby,T
AU  - Moore,CE
AU  - Hoefer,N
AU  - McComb,DW
AU  - Sevov,CS
AU  - Badji,JD
DO  - 10.1002/anie.202211304
PY  - 2022///
TI  - Closed Aromatic Tubes-Capsularenes.
T2  - Angew Chem Int Ed Engl
UR  - http://dx.doi.org/10.1002/anie.202211304
UR  - https://www.ncbi.nlm.nih.gov/pubmed/35981224
VL  - 61
ER  -
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