Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/161106
Title: Selenium and tellurium derivatives of corannulene: serendipitous discovery of a one-dimensional stereoregular coordination polymer crystal based on Te-O backbone and side-chain aromatic array
Authors: Barát, Viktor
Stuparu, Mihaiela Corina
Keywords: Science::Chemistry
Engineering::Materials
Issue Date: 2020
Source: Barát, V. & Stuparu, M. C. (2020). Selenium and tellurium derivatives of corannulene: serendipitous discovery of a one-dimensional stereoregular coordination polymer crystal based on Te-O backbone and side-chain aromatic array. Chemistry - A European Journal, 26(66), 15135-15139. https://dx.doi.org/10.1002/chem.202003989
Project: 2019-T1-002-066 
RG106/19 
2018-T1-001-176 
RG18/18 
A1883c0006 
04INS000171C230 
Journal: Chemistry - A European Journal 
Abstract: Monobromo-, tetrabromo-, and pentachloro-corannulene are subjected to nucleophilic substitution reactions with tolyl selenide and phenyl telluride-based nucleophiles generated in situ from the corresponding dichalcogenides. In the case of selenium nucleophile, the reaction provides moderate yields (52-77 %) of the targeted corannulene selenoethers. A subsequent oxidation of the selenium atoms proceeds smoothly to furnish corannulene selenones in 81-93 % yield. In the case of tellurides, only monosubstitution of the corannulene scaffold could be achieved albeit with concomitant oxidation of the tellerium atom. Unexpectedly, this monotelluroxide derivative of corannulene (RR'Te=O, R=Ph, R'=corannulene) is observed to form a linear coordination polymer chain in the crystalline state. In this chain, Te-O constitutes the polymer backbone around which the aromatic groups (R and R') arrange as polymer side-chains. The polymer crystal is stabilized through intramolecular π-π stacking interactions of the side-chains and intermolecular hydrogen and halogen bonding interactions with the solvent (chloroform) molecules. Interestingly, each diad of the polymer chain is racemic. Therefore, in terms of stereoregularity, the polymer chain can be described as syndiotactic.
URI: https://hdl.handle.net/10356/161106
ISSN: 0947-6539
DOI: 10.1002/chem.202003989
Schools: School of Physical and Mathematical Sciences 
School of Materials Science and Engineering 
Rights: © 2020 Wiley-VCH GmbH. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1002/chem.202003989.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:MSE Journal Articles
SPMS Journal Articles

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