Multielectron photoredox catalysts based on charge accumulation in conjugated macrocycles
Lead Research Organisation:
Imperial College London
Department Name: Chemistry
Abstract
The proposal will develop new types of conjugated macrocycles for multielectron photoredox catalysis. The macrocycles are designed to overcome the current challenges of accumulation and transfer of multiple charges by switching between different aromatic states, extending the scope of photoredox catalysis from single- to multielectron transfer reactions and opening up exciting new avenues for solar fuel production and organic synthesis. The research team of Dr Florian Glöcklhofer, Dr Felix Plasser and Prof Martin Heeney bring complementary expertise to develop molecules and materials with previously unattained properties.
Publications
Aniés F
(2023)
A comparison of para , meta , and ortho -carborane centred non-fullerene acceptors for organic solar cells
in Journal of Materials Chemistry C
Aniés F
(2024)
A Conjugated Carboranyl Main Chain Polymer with Aggregation-Induced Emission in the Near-Infrared.
in Journal of the American Chemical Society
Aniés F
(2023)
In Situ Generation of n-Type Dopants by Thermal Decarboxylation
in Advanced Functional Materials
Bennett TLR
(2023)
Functionalisation of conjugated macrocycles with type I and II concealed antiaromaticity via cross-coupling reactions.
in Molecular systems design & engineering
Do Casal MT
(2023)
Classification of doubly excited molecular electronic states.
in Chemical science
Eder S
(2022)
Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials.
in Angewandte Chemie (International ed. in English)
Eder S
(2022)
Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials.
in Angewandte Chemie (Weinheim an der Bergstrasse, Germany)
Fukazawa Y
(2023)
Mechanistic Insight into Palladium-Catalyzed Asymmetric Alkylation of Indoles with Diazoesters Employing Bipyridine- N , N' -dioxides as Chiral Controllers
in Advanced Synthesis & Catalysis
| Description | Methods have been developed to allow for the synthesis of molecular systems in which the key properties can be readily tuned. Tuning is important to develop catalytic materials which can be tuned for certain applications - for example carbon dioxide reduction. |
| Exploitation Route | The basic materials have been prepared and their fundamental properties investigated. They now need to be tested in photocatalytic applications. This is a proof of concept grant, so requires follow-on funding for further investigation. In the current absence of such funding, collaborators are being sought to perform these studies. |
| Sectors | Chemicals Energy |
| Title | CCDC 2164513: Experimental Crystal Structure Determination |
| Description | Related Article: Xiantao Hu, Ram Datt, Qiao He, Panagiota Kafourou, Harrison Ka Hin Lee, Andrew J. P. White, Wing Chung Tsoi, Martin Heeney|2022|J.Mater.Chem.C|10|9249|doi:10.1039/D2TC01433E |
| Type Of Material | Database/Collection of data |
| Year Produced | 2022 |
| Provided To Others? | Yes |
| URL | http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2bnc0d&sid=DataCite |
| Title | CCDC 2164514: Experimental Crystal Structure Determination |
| Description | Related Article: Xiantao Hu, Ram Datt, Qiao He, Panagiota Kafourou, Harrison Ka Hin Lee, Andrew J. P. White, Wing Chung Tsoi, Martin Heeney|2022|J.Mater.Chem.C|10|9249|doi:10.1039/D2TC01433E |
| Type Of Material | Database/Collection of data |
| Year Produced | 2022 |
| Provided To Others? | Yes |
| URL | http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2bnc1f&sid=DataCite |
| Title | CCDC 2168620: Experimental Crystal Structure Determination |
| Description | Related Article: Yasuaki Fukazawa, Vladimir Yu. Vaganov, Julia V. Burykina, Artem N. Fakhrutdinov, Ruslan I. Safiullin, Felix Plasser, Aleksandr E. Rubtsov, Valentine P. Ananikov, Andrei V. Malkov|2024|Adv.Synth.Catal.|336|121|doi:10.1002/adsc.202300845 |
| Type Of Material | Database/Collection of data |
| Year Produced | 2024 |
| Provided To Others? | Yes |
| URL | http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2bsmh8&sid=DataCite |
| Title | CCDC 2170729: Experimental Crystal Structure Determination |
| Description | Related Article: Simon Eder, Bowen Ding, Daisy B. Thornton, Darlene Sammut, Andrew J. P. White, Felix Plasser, Ifan E. L. Stephens, Martin Heeney, Stefano Mezzavilla, Florian Glöcklhofer|2023|Angew.Chem.,Int.Ed.|61||doi:10.1002/anie.202212623 |
| Type Of Material | Database/Collection of data |
| Year Produced | 2023 |
| Provided To Others? | Yes |
| URL | http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2bvtjk&sid=DataCite |
| Title | CCDC 2170730: Experimental Crystal Structure Determination |
| Description | Related Article: Simon Eder, Bowen Ding, Daisy B. Thornton, Darlene Sammut, Andrew J. P. White, Felix Plasser, Ifan E. L. Stephens, Martin Heeney, Stefano Mezzavilla, Florian Glöcklhofer|2023|Angew.Chem.,Int.Ed.|61||doi:10.1002/anie.202212623 |
| Type Of Material | Database/Collection of data |
| Year Produced | 2023 |
| Provided To Others? | Yes |
| URL | http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2bvtkl&sid=DataCite |
| Title | Computational Research Data underlying the manuscript "Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials" |
| Description | Computational Research Data underlying the manuscript "Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials" by Simon Eder, Daisy B. Thornton, Bowen Ding, Darlene Sammut, Andrew J. P. White, Felix Plasser, Ifan E. L. Stephens, Martin Heeney, Stefano Mezzavilla, and Florian Glöcklhofer. Content (names of files and folders are given in bold face) Computations were performed on SqTA, SqTI-Bu, SqTI-Ph, SqNa - as described in the text. The folder for each molecule contains subfolders for the individual electronic states: OPT_neut: neutral singlet state OPT_T1: neutral triplet state OPT_1M: charged state (1-) OPT_2M: charged state (2-) etc. VIST: files for VIST analysis. Each optimisation folder contains the following: qchem.[in/out]: Q-Chem input/output for geometry optimisation final.xyz: optimised geometry Freq/qchem[.in,.out]: Q-Chem input/output files for vibrational frequency analysis SOLV/qchem[.in,.out]: Q-Chem input/output files for solvated calculation used to determine redox potentials tNICS/gaussian[.com,.log]: Gaussian input/output files for NICS computation underlying the VIST plots |
| Type Of Material | Database/Collection of data |
| Year Produced | 2022 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Computational_Research_Data_underlying_the_manuscrip... |
| Title | Research Data for "3D Visualisation of chemical shielding tensors (VIST) to elucidate local and global (anti)aromaticity" |
| Description | Research data underlying the manuscript "3D Visualisation of local aromaticity and antiaromaticity using chemical shielding tensors" ContentMolecular coordinates (coord.xyz), Gaussian input files (gaussian.com), Gaussian output files (gaussian.log), and VMD input scripts (*.vmd) for benzene, phenanthrene, cyclobutaphenanthrene, PCT (paracyclophanetetraene), 8CPP (cycloparaphenylene), norcorrole_dimer. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_3D_Visualisation_of_chemical_shiel... |
| Title | Research Data for "3D Visualisation of chemical shielding tensors (VIST) to elucidate local and global (anti)aromaticity" |
| Description | Research data underlying the manuscript "3D Visualisation of local aromaticity and antiaromaticity using chemical shielding tensors" ContentMolecular coordinates (coord.xyz), Gaussian input files (gaussian.com), Gaussian output files (gaussian.log), and VMD input scripts (*.vmd) for benzene, phenanthrene, cyclobutaphenanthrene, PCT (paracyclophanetetraene), 8CPP (cycloparaphenylene), norcorrole_dimer. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_3D_Visualisation_of_chemical_shiel... |
| Title | Research Data for "Exploitation of Baird aromaticity and Clar's rule for tuning the triplet energies of polycyclic aromatic hydrocarbons" |
| Description | Research data underlying the manuscript "Exploitation of Baird aromaticity and Clar's rule for tuning the triplet energies of polycyclic aromatic hydrocarbons" Content (names of folders and files are given in bold face) Computations performed on benzene, cyclobutadiene (CBD), biphenylene, and molecules 3,4,5 (Mol3, Mol4, Mol5) as defined in the text considering the singlet and triplet states. The individual folders contain the molecular coordinates (final.xyz), Gaussian input / output files (gaussian.com / gaussian.log) of NICS computations, TheoDORE output (NICS.out) with NICS eigenvalues. The singlet folders also contain Q-Chem input / output (qchem.in / qchem.out) files for the vertical excitations. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_Exploitation_of_Baird_aromaticity_... |
| Title | Research Data for "Exploitation of Baird aromaticity and Clar's rule for tuning the triplet energies of polycyclic aromatic hydrocarbons" |
| Description | Research data underlying the manuscript "Exploitation of Baird aromaticity and Clar's rule for tuning the triplet energies of polycyclic aromatic hydrocarbons" Content (names of folders and files are given in bold face) Computations performed on benzene, cyclobutadiene (CBD), biphenylene, and molecules 3,4,5 (Mol3, Mol4, Mol5) as defined in the text considering the singlet and triplet states. The individual folders contain the molecular coordinates (final.xyz), Gaussian input / output files (gaussian.com / gaussian.log) of NICS computations; TheoDORE output (NICS.out) with NICS eigenvalues; Q-Chem input / output (qchem.in / qchem.out) files for the vertical excitations; OpenMolcas input / output files (MOLCAS.input / molcas.log) for CASPT2 computations. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_Exploitation_of_Baird_aromaticity_... |
| Title | Research Data for "Exploitation of Baird aromaticity and Clar's rule for tuning the triplet energies of polycyclic aromatic hydrocarbons" |
| Description | Research data underlying the manuscript "Exploitation of Baird aromaticity and Clar's rule for tuning the triplet energies of polycyclic aromatic hydrocarbons" Content (names of folders and files are given in bold face) Computations performed on benzene, cyclobutadiene (CBD), biphenylene, and molecules 3,4,5 (Mol3, Mol4, Mol5) as defined in the text considering the singlet and triplet states. The individual folders contain the molecular coordinates (final.xyz), Gaussian input / output files (gaussian.com / gaussian.log) of NICS computations; TheoDORE output (NICS.out) with NICS eigenvalues; Q-Chem input / output (qchem.in / qchem.out) files for the vertical excitations; OpenMolcas input / output files (MOLCAS.input / molcas.log) for CASPT2 computations. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_Exploitation_of_Baird_aromaticity_... |
| Title | Research Data for "Functional Group Introduction and Aromatic Unit Variation in a Set of p-Conjugated Macrocycles: Revealing the Central Role of Local and Global Aromaticity" |
| Description | Research Data underlying the manuscript "Functional Group Introduction and Aromatic Unit Variation in a Set of p-Conjugated Macrocycles: Revealing the Central Role of Local and Global Aromaticity" by Martina Rimmele, Wojciech Nogala, Maryam Seif-Eddine, Maxie M. Roessler, Martin Heeney, Felix Plasser, and Florian Glöcklhofer Content (names of folders and files are given in bold face). Computations performed on the molecules BCyc, BCyc-Et, NCyc-Et, ACyc-Et, and PCyc-Et as described in the text. The folder for each molecule contains subfolders for the individual electronic states:- OPT_neut: neutral singlet state- OPT_Trip: neutral triplet state- OPT_2P: charged state (2+)- OPT_2M: charged state (2-)- etc. Each optimisation folder contains the following:- qchem.in: input for geometry optimisation- final.xyz: optimised geometry- CHARAC/qchem[.in,.out]: Input/output file for Hessian-free characterisation of stationary points- SOLV/qchem[.in,.out]: Input/output file for solvated calculation used to determine redox potentials- VEXS/qchem[.in,.out]: Input/output file for vertical excitation- VEXS/libwfa_summ.txt: Compact summary of excitation energies- tNICS/gaussian[.com,.log]: Input/output file for NICS computation underlying the VIST plots |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_Functional_Group_Introduction_and_... |
| Title | Research Data for "Functional Group Introduction and Aromatic Unit Variation in a Set of p-Conjugated Macrocycles: Revealing the Central Role of Local and Global Aromaticity" |
| Description | Research Data underlying the manuscript "Functional Group Introduction and Aromatic Unit Variation in a Set of p-Conjugated Macrocycles: Revealing the Central Role of Local and Global Aromaticity" by Martina Rimmele, Wojciech Nogala, Maryam Seif-Eddine, Maxie M. Roessler, Martin Heeney, Felix Plasser, and Florian Glöcklhofer Content (names of folders and files are given in bold face). Computations performed on the molecules BCyc, BCyc-Et, NCyc-Et, ACyc-Et, and PCyc-Et as described in the text. The folder for each molecule contains subfolders for the individual electronic states:- OPT_neut: neutral singlet state- OPT_Trip: neutral triplet state- OPT_2P: charged state (2+)- OPT_2M: charged state (2-)- etc. Each optimisation folder contains the following:- qchem.in: input for geometry optimisation- final.xyz: optimised geometry- CHARAC/qchem[.in,.out]: Input/output file for Hessian-free characterisation of stationary points- SOLV/qchem[.in,.out]: Input/output file for solvated calculation used to determine redox potentials- VEXS/qchem[.in,.out]: Input/output file for vertical excitation- VEXS/libwfa_summ.txt: Compact summary of excitation energies- tNICS/gaussian[.com,.log]: Input/output file for NICS computation underlying the VIST plots |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_Functional_Group_Introduction_and_... |
| Title | Research Data for "The role of excited-state character, structural relaxation, and symmetry breaking in enabling delayed fluorescence activity in push-pull chromophores" |
| Description | Research data underlying the manuscript "The role of excited-state character, structural relaxation, and symmetry breaking in enabling delayed fluorescence activity in push-pull chromophores" by P. Kimber, P. Goddard, I. A. Wright, and F. Plasser. Content (names of folders and files are given in bold face) Computations were performed on Cz-AQ (AQ), Cz-BDT BDT), Cz-BDF (BDF), Cz-BDT-SO2 (BDT-SO2) as defined in the text. These folders contain subfolders for:- OPT.wB97X-V: Geometry optimisation at the wB97X-V level using Ci and C2 symmetry - VEX: Vertical excitations in gas phase using the methods described in the text- EX_OPT_wPBEh: Optimisation of excited state minima in solution using LR-PCM including vertical excitations (VEX) at the optimised geometries- state-specific-solvation: ptSS, SS-PCM, and UKS/PCM single point jobs as defined in the text The folders contain the following files- coord.qcin: Input geometry for Q-Chem- final.xyz: Final geometry after geometry optimisation- qchem.in: Input file for Q-Chem- qchem.out: Output file for Q-Chem |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_The_role_of_excited-state_characte... |
| Title | Research Data for "The role of excited-state character, structural relaxation, and symmetry breaking in enabling delayed fluorescence activity in push-pull chromophores" |
| Description | Research data underlying the manuscript "The role of excited-state character, structural relaxation, and symmetry breaking in enabling delayed fluorescence activity in push-pull chromophores" by P. Kimber, P. Goddard, I. A. Wright, and F. Plasser. Content (names of folders and files are given in bold face) Computations were performed on Cz-AQ (AQ), Cz-BDT BDT), Cz-BDF (BDF), Cz-BDT-SO2 (BDT-SO2) as defined in the text. These folders contain subfolders for:- OPT.wB97X-V: Geometry optimisation at the wB97X-V level using Ci and C2 symmetry - VEX: Vertical excitations in gas phase using the methods described in the text- EX_OPT_wPBEh: Optimisation of excited state minima in solution using LR-PCM including vertical excitations (VEX) at the optimised geometries- state-specific-solvation: ptSS, SS-PCM, and UKS/PCM single point jobs as defined in the text The folders contain the following files- coord.qcin: Input geometry for Q-Chem- final.xyz: Final geometry after geometry optimisation- qchem.in: Input file for Q-Chem- qchem.out: Output file for Q-Chem |
| Type Of Material | Database/Collection of data |
| Year Produced | 2021 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Research_Data_for_The_role_of_excited-state_characte... |
| Title | Research data for "[2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(p-phenylene vinylene)s (PPVs)" |
| Description | This dataset contains the underlying experimental (1H NMR, 13C NMR, 31P NMR, high-resolution mass spectrometry (HRMS), UV-vis absorption, photoluminescence (PL), cyclic voltammetry) and computational (molecular geometries, input/output files for Q-Chem, Gaussian, and TheoDORE) research data for the article "[2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(p-phenylene vinylene)s (PPVs)". Content (names of folders and files are given in bold face): The folder for each molecule (Br-P2, O-3, O-P1, O-PCT, PCT, Quinine, S-2, S-3, S-P1, S-P2, S-PCT) contains the molecular structure as .mol and .cdxml file, as well as subfolders for the Experimental research data and, if available, the Computational research data. The Experimental research data folder for each molecule contains the measurement files. The file names are composed of the acronym of the measured molecule, the type of measurement, and further details about the measurement (if needed to distinguish the files). Measurements were performed as described in the article. Computations were performed on the molecules O-PCT and S-PCT as described in the article. The Computational research data folder for each molecule contains subfolders for geometry optimisations of the individual electronic states and rotamers: c2_neut: neutral singlet state for C2 rotamer c2_trip: T1 state of C2 rotamer c2_2P: charged state (2+) of C2 rotamer c2_2M: charged state (2-) of C2 rotamer cs_neut: neutral singlet state for Cs rotamer etc. Additional content: TS: Full transition state optimisation TS_constrained: constrained transition state optimisation VIST: Data for VIST plots FROZEN: Computations for frozen PCT structure (denoted O/S-PCT@PCT in the article) Each optimisation folder contains the following: qchem.[in,out]: input/output for geometry optimisation final.xyz: optimised geometry SOLV/qchem.[in,out]: input/output for solvated single-point computation tNICS/gaussian.[com,log]: input/output for NMR shielding tensors |
| Type Of Material | Database/Collection of data |
| Year Produced | 2022 |
| Provided To Others? | Yes |
| URL | https://zenodo.org/record/5206264 |
| Title | Supplementary information files for Mechanistic insight into Pd-catalyzed asymmetric alkylation of indoles with diazoesters employing bipyridine-N,N'-dioxides as chiral controllers |
| Description | Supplementary files for article Mechanistic insight into Pd-catalyzed asymmetric alkylation of indoles with diazoesters employing bipyridine-N,N'-dioxides as chiral controllersMetal-catalyzed asymmetric alkylation of indoles with a-diazoesters is well-known, however, the underlying mechanisms of this reaction, particularly the origin of stereoselectivity, remain uncertain. For the Pd catalysis, we address this cutting-edge challenge from two complementary viewpoints - i) the molecular level regarding a single catalytically active Pd center; and ii) nano-level Pd species investigating the factors favoring the appearance of the preferred catalytic centers. The formation of the active catalytic species was monitored by structural methods (NMR and ESI-MS), and metal particles were characterized with electron microscopy (SEM, EDX). On the molecular level,chiral bipyridine-N,N'-dioxides proved to be competent chiral controllers. The kinetic and DFT computational data revealed a crucial role of water in the rate and selectivity determining steps and showed that the enantioselectivity of the process is controlled by the protodepalladation step. On the nano-scale, the important effect of catalyst precursor on the overall reaction performance was shown. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2024 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Supplementary_information_files_for_Mechanistic_insi... |
| Title | Supplementary information files for Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity |
| Description | Supplementary information files for article Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity Aromaticity is a central concept in chemistry, pervading areas from biochemistry to materials science. Recently, chemists also started to exploit intricate phenomena such as the interplay of local and global (anti)aromaticity or aromaticity in non-planar systems and three dimensions. These phenomena pose new challenges in terms of our fundamental understanding and the practical visualisation of aromaticity. To overcome these challenges, a method for the visualisation of chemical shielding tensors (VIST) is developed here that allows for a 3D visualisation with quantitative information about the local variations and anisotropy of the chemical shielding. After exemplifying the method in different planar hydrocarbons, we study two non-planar macrocycles to show the unique benefits of the VIST method for molecules with competing p-conjugated systems and conclude with a norcorrole dimer showing clear evidence of through-space aromaticity. We believe that the VIST method will be a highly valuable addition to the computational toolbox. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2022 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Supplementary_information_files_for_Visualisation_of... |
| Title | Supplementary information files for Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity |
| Description | Supplementary information files for article Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity Aromaticity is a central concept in chemistry, pervading areas from biochemistry to materials science. Recently, chemists also started to exploit intricate phenomena such as the interplay of local and global (anti)aromaticity or aromaticity in non-planar systems and three dimensions. These phenomena pose new challenges in terms of our fundamental understanding and the practical visualisation of aromaticity. To overcome these challenges, a method for the visualisation of chemical shielding tensors (VIST) is developed here that allows for a 3D visualisation with quantitative information about the local variations and anisotropy of the chemical shielding. After exemplifying the method in different planar hydrocarbons, we study two non-planar macrocycles to show the unique benefits of the VIST method for molecules with competing p-conjugated systems and conclude with a norcorrole dimer showing clear evidence of through-space aromaticity. We believe that the VIST method will be a highly valuable addition to the computational toolbox. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2022 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Supplementary_information_files_for_Visualisation_of... |
| Title | Supplementary information for Squarephaneic tetraanhydride: a conjugated square-shaped cyclophane for the synthesis of porous organic materials |
| Description | Supplementary files for article Squarephaneic tetraanhydride: a conjugated square-shaped cyclophane for the synthesis of porous organic materialsAromatic carboxylic anhydrides are ubiquitous building blocks in organic materials chemistry and have received considerable attention in the synthesis of organic semiconductors, pigments, and battery electrode materials. Here we extend the family of aromatic carboxylic anhydrides with a unique new member, a conjugated cyclophane with four anhydride groups. The cyclophane is obtained in a three-step synthesis and can be functionalised efficiently, as shown by the conversion into tetraimides and an octacarboxylate. Crystal structures reveal the high degree of porosity achievable with the new building block. Excellent electrochemical properties and reversible reduction to the tetraanions are shown for the imides; NMR and EPR measurements confirm the global aromaticity of the dianions and evidence the global Baird aromaticity of the tetraanions. Considering the short synthesis and unique properties, we expect widespread use of the new building block in the development of organic materials. |
| Type Of Material | Database/Collection of data |
| Year Produced | 2023 |
| Provided To Others? | Yes |
| URL | https://repository.lboro.ac.uk/articles/dataset/Supplementary_information_for_Squarephaneic_tetraanh... |
| Description | Jang Wook Choi |
| Organisation | Seoul National University |
| Country | Korea, Republic of |
| Sector | Academic/University |
| PI Contribution | Testing of performance of new macrocycles in battery application |
| Collaborator Contribution | Battery testing and characterisation |
| Impact | Papers in preparation. Multi-discplinary. Chemistry and physics |
| Start Year | 2021 |