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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(04): 330-335
DOI: 10.1055/s-0040-1721101
Focus Issue: Curved Organic π-Systems
Short Communication

Synthesis of a Tetraepoxy Nanobelt and Its Reductive Aromatization Attempts

Yi Han 
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Shaoqiang Dong
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Yuan Cheng Liau
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Chunyan Chi 
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
› Author Affiliations Funding Information We acknowledge financial support from the MOE Tier 1 grant (R-143-000-B62-114) and Tier 2 grant (MOE2018-T2-1-152).
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Abstract

Hydrocarbon nanobelts have recently attracted tremendous interest. Herein, we report our recent progress towards the synthesis of a newly designed hydrocarbon nanobelt tetrabenzo[10]cyclacene, which can be regarded as a sidewall fragment of the (10,0) carbon nanotube. The structures of both key intermediates — “U”-shape diepoxy building block and tetraepoxy nanobelt — were confirmed by single-crystal X-ray diffraction. Our preliminary reductive aromatization reactions revealed that a tetrahydrogenated species instead of tetrabenzo[10]cyclacene was formed during this process. Computational results further revealed that hydrogenation can lead to significant strain release of the backbone structure of tetrabenzo[10]cyclacene, which may attribute to the absence of the target compound during the reductive aromatization.

Key words

hydrocarbon nanobelts - reductive aromatization - hydrogenation - strain

Supporting Information

Supporting Information for this article is available online at http://doi.org/10.1055/s-0040-1721101.


Supporting Information



Publication History

Received: 13 September 2020

Accepted: 09 October 2020

Article published online:
18 December 2020

© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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