Template-Directed Synthesis of Cyclocarbon Catenanes
Lead Research Organisation:
UNIVERSITY OF OXFORD
Department Name: Oxford Chemistry
Abstract
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Organisations
People |
ORCID iD |
| Harry Anderson (Primary Supervisor) | |
| Connor Patrick (Student) |
Publications
Anderson H
(2021)
A Short History of Cyclocarbons
in Bulletin of the Chemical Society of Japan
Patrick CW
(2022)
Polyyne [3]Rotaxanes: Synthesis via Dicobalt Carbonyl Complexes and Enhanced Stability.
in Angewandte Chemie (International ed. in English)
Patrick C
(2022)
Towards polyyne rotaxanes and catenanes
Studentship Projects
| Project Reference | Relationship | Related To | Start | End | Student Name |
|---|---|---|---|---|---|
| EP/N509711/1 | 30/09/2016 | 29/09/2021 | |||
| 2124672 | Studentship | EP/N509711/1 | 30/09/2018 | 30/03/2022 | Connor Patrick |
| NE/W502728/1 | 31/03/2021 | 30/03/2022 | |||
| 2124672 | Studentship | NE/W502728/1 | 30/09/2018 | 30/03/2022 | Connor Patrick |
| Description | This award has been used to fund a project that aims to develop route to carbon-rich molecules. The project can be split into two main areas of achievement: 1. We have successfully prepared long polyyne [3]rotaxanes with up to 14 contiguous acetylene units in length. The physical properties of these [3]rotaxanes were compared to the analogous (non-interlocked) dumbbells. It was found that the interlocked polyynes were markedly more stable (up to 4.5 times more stable, as evaluated by UV-vis methods) than the non-interlocked counterparts. Importantly, while these rotaxanes show improved stability, we verified very little changed in their physical properties (by NMR and optical spectroscopic methods). This work has confirmed that mechanically interlocked polyynes remain a promising approach to building up much longer, more stable polyynes. 2. We have successfully prepared masked cyclocarbon [n]catenanes and polyyne [n]rotaxanes of varying size/length. While this important milestone was met only very recently, work is already underway at 'unmasking' these compounds the yield polyyne shielded polyynes of unprecedented length. Additionally, unmasking the cyclic analogue could give access to cyclocarbon [n]catenanes - a cyclic ring of carbon atoms that has piqued academic interest for years, but has yet to be experimentally isolated. |
| Exploitation Route | These findings not only confirm that supramolecular encapsulation brings about a significant improvement in the stability of these, otherwise, highly reactive systems, but has also demonstrated a novel approach to building increasingly large carbon-rich systems. We expect this work would be used be researchers in the field to prepare a multitude of other carbon-rich systems. This work would also be taken forward in our research group. We aim to prepare these exciting compounds in higher yields (allowing more in-depth studies into them) and also to generate larger systems. The physical properties of these could then be evaluated. |
| Sectors | Electronics Energy |