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Conjugated macrocycles for battery electrodes

Conjugated macrocycles for battery electrodes

Florian Philipp Glöcklhofer (ORCID: 0000-0002-6911-8563)
  • Grant DOI 10.55776/J4463
  • Funding program Erwin Schrödinger
  • Status ended
  • Start September 1, 2020
  • End May 31, 2024
  • Funding amount € 162,290
  • Project website

Disciplines

Chemistry (100%)

Keywords

    Synthetic organic chemistry, Molecular architecture and structure, Structural properties of materials, Method development in chemistry, Organic battery electrodes, Synthetic organic chemistry, Molecular architecture and structure, Structural properties of

Abstract Final report

Organic materials hold great promise for becoming the next generation of battery electrode materials. This project explores a fundamentally new concept for such materials, significantly improving thei r c hemical s tability a nd electronic conductivity. It bridges the gap between research on fundamental effects in organic mater ials a nd the development of ground-breaking applications. Batteries can help to reduce carbon dioxide emissions by storing clean electricity fr om r enewable s ources for periods with high demand and by making the electricity available for the tr a nsport s ector, power ing el ec tric vehicles and other means of transport. However, while batteries and electric vehicles can help to r educ e c arbon dioxide emissions, the widespread use of batteries comes at a cost. There are severe environmental a nd ethic al issues associated with lithium-ion batteries, the type of batteries dominating the electric vehicle market. Furthermore, the future supply of materials required for battery manufacturing is a concern. Most notably, lithium- ion batteries usually require cobalt for their positive electrode, which is often mi ned under ter rible wor king conditions. Organic materials are a promising alternative to electrode materials based on c obalt a nd other hea vy meta ls, considering their advantages of recyclability, structural diversity, fl ex ibility , a nd c ompatibility wi th s odium (replacing the less abundant lithium). In fact, they hold great promise for becoming the next generation of ba tter y electrode materials. However, limited electronic properties and insufficient chemical stability under fast- charge/discharge conditions still impede commercial application of these materials. To solve these issues, this project explores a fundamentally new concept for storing electricity in organic materials, based on so-called conjugated macrocycles. In particular, the research addresses the challenges of achieving high stability and capacity of the organic materials. It will further provide new synthetic strategies and design guidelines for the path towards large-scale application, with the ultimate goal of decreasing carbon dioxide emi ssions i n a n ethical and sustainable way.

Conjugated macrocycles: a promising future for organic battery technology Imagine a battery that's better for the environment, charges faster and stores more energy. That's the potential of conjugated macrocycles, a new class of organic materials explored in this research project. These materials could replace current battery electrode materials, which are often based on heavy metals and require the use of limited resources such as lithium ions. The project focused on a particular type of conjugated macrocycle called paracyclophanetetraene (PCT). The researchers discovered that PCT offers many advantages for battery electrodes. It shows remarkable stability during charge and discharge cycles, charges and discharges quickly, and can have a high energy storage capacity. PCT's unique molecular structure allows it to effectively stabilise both neutral and charged states, which is crucial for ensuring long-term functionality and efficiency in batteries. A key finding was that PCT's macrocyclic structure creates voids in the solid-state packing, which allows the material to accommodate sodium ions, contributing to its excellent performance using these more abundant and less expensive ions. However, the project did not stop at the discovery of PCT as promising material. The researchers also looked at ways to improve PCT for battery applications. By introducing different chemical groups, they were able to fine-tune properties such as stability and capacity. They also investigated methods to reduce the solubility of PCT, a key factor in preventing the electrode material from dissolving in the battery electrolyte. The results of the project show that conjugated macrocycles provide a promising new avenue for battery technology. While further research is needed for practical application, this project has laid the groundwork for significant advances in battery development.

Research institution(s)
  • Technische Universität Wien - 100%
  • Imperial College London - 100%

Research Output

  • 80 Citations
  • 20 Publications
  • 13 Datasets & models
  • 2 Scientific Awards
  • 1 Fundings
Publications
  • 2024
    Title Reducing undesired solubility of squarephaneic tetraimide for use as an organic battery electrode material.
    DOI 10.1039/d3fd00145h
    Type Journal Article
    Author Bhosale M
    Journal Faraday discussions
    Pages 129-144
  • 2024
    Title Organic neuromorphics and bioelectronics: general discussion.
    DOI 10.1039/d4fd90006e
    Type Journal Article
    Author Aitchison Cm
    Journal Faraday discussions
    Pages 83-95
  • 2024
    Title Organic batteries: general discussion.
    DOI 10.1039/d4fd90007c
    Type Journal Article
    Author Aitchison Cm
    Journal Faraday discussions
    Pages 145-161
  • 2025
    Title Soluble Conjugated Polymers without Side Chains: Macrocycles as Comonomers
    DOI 10.26434/chemrxiv-2025-jbkg8
    Type Preprint
    Author Moro S
  • 2024
    Title Excitonic organic materials for photochemical and optoelectronic applications: general discussion.
    DOI 10.1039/d4fd90008a
    Type Journal Article
    Author Aitchison Cm
    Journal Faraday discussions
    Pages 298-334
  • 2021
    Title The influence of alkyl group regiochemistry and backbone fluorination on the packing and transistor performance of N -cyanoimine functionalised indacenodithiophenes
    DOI 10.1039/d1ma00091h
    Type Journal Article
    Author Hodsden T
    Journal Materials Advances
    Pages 1706-1714
    Link Publication
  • 2021
    Title Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity
    DOI 10.26434/chemrxiv.13580885.v2
    Type Preprint
    Author Plasser F
    Link Publication
  • 2021
    Title Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity
    DOI 10.26434/chemrxiv.13580885
    Type Preprint
    Author Plasser F
    Link Publication
  • 2021
    Title 3D Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity
    DOI 10.26434/chemrxiv.13580885.v1
    Type Preprint
    Author Plasser F
    Link Publication
  • 2021
    Title Functional Group Introduction and Aromatic Unit Variation in a Set of p-Conjugated Macrocycles: Revealing the Central Role of Local and Global Aromaticity
    DOI 10.26434/chemrxiv.14485002.v1
    Type Preprint
    Author Rimmele M
    Link Publication
  • 2021
    Title Functional Group Introduction and Aromatic Unit Variation in a Set of p-Conjugated Macrocycles: Revealing the Central Role of Local and Global Aromaticity
    DOI 10.26434/chemrxiv.14485002
    Type Preprint
    Author Rimmele M
    Link Publication
  • 2021
    Title Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity**
    DOI 10.1002/ejoc.202100352
    Type Journal Article
    Author Plasser F
    Journal European Journal of Organic Chemistry
    Pages 2529-2539
    Link Publication
  • 2022
    Title Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials
    DOI 10.26434/chemrxiv-2022-p4p5d
    Type Preprint
    Author Eder S
    Link Publication
  • 2022
    Title Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials**
    DOI 10.1002/ange.202212623
    Type Journal Article
    Author Eder S
    Journal Angewandte Chemie
    Link Publication
  • 2022
    Title Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials**
    DOI 10.1002/anie.202212623
    Type Journal Article
    Author Eder S
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2022
    Title Post-polymerisation approaches for the rapid modification of conjugated polymer properties
    DOI 10.1039/d2mh00519k
    Type Journal Article
    Author Rimmele M
    Journal Materials Horizons
    Pages 2678-2697
    Link Publication
  • 2022
    Title [2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly( p-phenylene vinylene)s (PPVs)
    DOI 10.12688/openreseurope.13723.2
    Type Journal Article
    Author Pletzer M
    Journal Open Research Europe
    Pages 111
    Link Publication
  • 2021
    Title Functional group introduction and aromatic unit variation in a set of p-conjugated macrocycles: revealing the central role of local and global aromaticity
    DOI 10.1039/d1qo00901j
    Type Journal Article
    Author Rimmele M
    Journal Organic Chemistry Frontiers
    Pages 4730-4745
    Link Publication
  • 2021
    Title [2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(p-phenylene vinylene)s (PPVs)
    DOI 10.12688/openreseurope.13723.1
    Type Journal Article
    Author Pletzer M
    Journal Open Research Europe
    Pages 111
    Link Publication
  • 2023
    Title Functionalisation of conjugated macrocycles with type I and II concealed antiaromaticity via cross-coupling reactions.
    DOI 10.1039/d3me00045a
    Type Journal Article
    Author Bennett Tlr
    Journal Molecular systems design & engineering
    Pages 713-720
Datasets & models
  • 2023 Link
    Title CCDC 2170729: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc2bvtjk
    Type Database/Collection of data
    Public Access
    Link Link
  • 2023 Link
    Title CCDC 2170730: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc2bvtkl
    Type Database/Collection of data
    Public Access
    Link Link
  • 2023 Link
    Title Research Data for "Functionalisation of conjugated macrocycles with Type I and II concealed antiaromaticity via cross-coupling reactions"
    DOI 10.17028/rd.lboro.22306207.v1
    Type Database/Collection of data
    Public Access
    Link Link
  • 2023 Link
    Title Research Data for "Reducing Undesired Solubility of Squarephaneic Tetraimide for Use as an Organic Battery Electrode Material"
    DOI 10.17028/rd.lboro.23685903
    Type Database/Collection of data
    Public Access
    Link Link
  • 2022 Link
    Title Research data for "[2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(p-phenylene vinylene)s (PPVs)"
    DOI 10.5281/zenodo.5206264
    Type Database/Collection of data
    Public Access
    Link Link
  • 2022 Link
    Title Research data for "[2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(p-phenylene vinylene)s (PPVs)"
    DOI 10.5281/zenodo.6323475
    Type Database/Collection of data
    Public Access
    Link Link
  • 2022 Link
    Title Supplementary information files for Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity
    DOI 10.17028/rd.lboro.19794796
    Type Database/Collection of data
    Public Access
    Link Link
  • 2021 Link
    Title CCDC 2050898: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc26v407
    Type Database/Collection of data
    Public Access
    Link Link
  • 2021 Link
    Title CCDC 2050899: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc26v418
    Type Database/Collection of data
    Public Access
    Link Link
  • 2021 Link
    Title Research data for "[2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(p-phenylene vinylene)s (PPVs)"
    DOI 10.5281/zenodo.5206265
    Type Database/Collection of data
    Public Access
    Link Link
  • 2021 Link
    Title Research Data for "3D Visualisation of chemical shielding tensors (VIST) to elucidate local and global (anti)aromaticity"
    DOI 10.17028/rd.lboro.13546826
    Type Database/Collection of data
    Public Access
    Link Link
  • 2021 Link
    Title Research Data for "Functional Group Introduction and Aromatic Unit Variation in a Set of π-Conjugated Macrocycles: Revealing the Central Role of Local and Global Aromaticity"
    DOI 10.17028/rd.lboro.14500482
    Type Database/Collection of data
    Public Access
    Link Link
  • 2021 Link
    Title Research Data for "Functional Group Introduction and Aromatic Unit Variation in a Set of π-Conjugated Macrocycles: Revealing the Central Role of Local and Global Aromaticity"
    DOI 10.17028/rd.lboro.14500482.v1
    Type Database/Collection of data
    Public Access
    Link Link
Scientific Awards
  • 2024
    Title Thieme Chemistry Journals Award
    Type Research prize
    Level of Recognition Continental/International
  • 2021
    Title Rising Star, Freiburg Rising Stars Academy, University of Freiburg
    Type Awarded honorary membership, or a fellowship, of a learned society
    Level of Recognition Continental/International
Fundings
  • 2021
    Title Multielectron photoredox catalysts based on charge accumulation in conjugated macrocycles
    Type Research grant (including intramural programme)
    Start of Funding 2021
    Funder Engineering and Physical Sciences Research Council (EPSRC)

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+43 1 505 67 40

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