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Karlsson, ChristofferORCID iD iconorcid.org/0000-0003-2883-2696
Publications (10 of 40) Show all publications
Norrehed, S., Karlsson, C., Light, M. E., Thapper, A., Huang, P. & Gogoll, A. (2019). Formation of persistent organic diradicals from N,N'-diphenyl-3,7- diazacyclooctanes. Monatshefte fuer Chemie, 150(1), 77-84
Open this publication in new window or tab >>Formation of persistent organic diradicals from N,N'-diphenyl-3,7- diazacyclooctanes
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2019 (English)In: Monatshefte fuer Chemie, ISSN 0026-9247, E-ISSN 1434-4475, Vol. 150, no 1, p. 77-84Article in journal (Refereed) Published
Abstract [en]

N,N'-Diphenyl-3,7-diazacyclooctane and structurally related N,N'-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C–C coupling reaction to produce dication–diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state.

Place, publisher, year, edition, pages
Vienna: Springer, 2019
Keywords
Biaryls, Crystal structure, Heterocycles, Oxidative coupling, biradicals
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-364531 (URN)10.1007/s00706-018-2298-4 (DOI)000454953600009 ()
Funder
Swedish Research Council
Available from: 2018-10-29 Created: 2018-10-29 Last updated: 2019-01-28Bibliographically approved
Karlsson, C., Strietzel, C., Huang, H., Sjödin, M. & Jannasch, P. (2018). Nonstoichiometric Triazolium Protic Ionic Liquids for All-Organic Batteries. ACS Applied Energy Materials (11), 6451-6462
Open this publication in new window or tab >>Nonstoichiometric Triazolium Protic Ionic Liquids for All-Organic Batteries
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2018 (English)In: ACS Applied Energy Materials, ISSN 2574-0962, no 11, p. 6451-6462Article in journal (Refereed) Published
Abstract [en]

Nonstoichiometric protic ionic liquids (NSPILs) are efficient electrolytes for protic electrochemical devices such as the all-organic proton battery, which has been suggested as a sustainable approach to energy storage. NSPILs contain a mixture of proton donors and acceptors and are ideal for this purpose due to their high proton conductivity, high electrochemical stability, low cost, and ease of synthesis. However, the electrolyte proton activity must be controlled carefully in these devices since it greatly influences the kinetics and energetics of the electrode redox reactions and, hence, also impacts battery device performance. In this study, specific NSPILs were designed and evaluated as electrolytes for the all-organic proton battery. The NSPILs were based on either 1,2,4-triazole or 1-methyl-1,2,4-triazole partially protonated with bis(trifluoromethylsulfonyl)imide (TFSI) to produce a range of NSPILs with different degrees of protonation. Both types of NSPIL investigated here exhibited a maximum conductivity of 1.2 S/cm (at 120 and 70 °C, respectively), and the eutectic composition of 1-methyl-1,2,4-triazolium TFSI also had high conductivity at 25 °C (24.9 mS/cm), superior to, e.g., imidazolium TFSI NSPILs. Pulsed field gradient NMR in conjunction with electrochemical impedance spectroscopy showed that the conductivity originated mainly from vehicle diffusion and proton hopping. Quinone functionalized poly(3,4-ethylenedioxythiophene) (PEDOT) electrodes exhibited reversible, fast, and stable redox conversion in these electrolytes, and a model is suggested to determine proton activities of NSPILs based on the quinone formal potential. An all-organic proton battery cell was assembled to demonstrate the usefulness of these electrolytes in devices. Fast and complete redox conversion with a cell potential of 0.45 V was demonstrated, even up to scan rates corresponding to 140 C. Compared to the pyridine based electrolytes used for the all-organic proton battery up until now, the present electrolytes display several advantages including lower melting point, lower toxicity, and compatibility with plastic materials.

Place, publisher, year, edition, pages
American Chemical Society, 2018
National Category
Materials Chemistry Inorganic Chemistry
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-364966 (URN)10.1021/acsaem.8b01389 (DOI)
Funder
SweGRIDS - Swedish Centre for Smart Grids and Energy Storage
Available from: 2018-11-07 Created: 2018-11-07 Last updated: 2019-02-07Bibliographically approved
Huang, H., Karlsson, C., Strømme, M., Gogoll, A. & Sjödin, M. (2017). Synthesis and Characterization of Poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole: investigation on Backbone/Pendant Interactions in a Conducting Redox Polymer. Physical Chemistry, Chemical Physics - PCCP, 19(16), 10427-10435
Open this publication in new window or tab >>Synthesis and Characterization of Poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole: investigation on Backbone/Pendant Interactions in a Conducting Redox Polymer
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2017 (English)In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 19, no 16, p. 10427-10435Article in journal (Refereed) Published
Abstract [en]

We herein report the synthesis and electrochemical characterization of poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole, consisting of a polypyrrole backbone derivatized at the beta position by a vinyl-hydroquinone pendant group. The structure of the polymer was characterized by solid state NMR spectroscopy. The interactions between the polypyrrole backbone and the oxidized quinone or reduced hydroquinone pendant groups are probed by several in situ methods. In situ attenuated total reflectance-Fourier transform infrared spectroscopy shows spectroscopic response from both the doping of the polymer backbone and the redox activity of the pendant groups. Using an in situ Electrochemical Quartz Crystal Microbalance we reveal that the polymer doping is unaffected by the pendant group redox chemistry, as opposed to previous reports. Despite the continuous doping the electrochemical conversion from the hydroquinone state to the quinone state results in a significant conductance drop, as observed by in situ conductivity measurements using an InterDigitated Array electrode set-up. Twisting of the conducting polymer backbone as a result of a decreased separation between pendant groups due to π-π stacking in the oxidized state is suggested as the cause of this conductance drop.

National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-316490 (URN)10.1039/c6cp08736a (DOI)000400117700025 ()28379225 (PubMedID)
Funder
Swedish Foundation for Strategic Research Swedish Research CouncilCarl Tryggers foundation Stiftelsen Olle Engkvist ByggmästareSwedish Energy AgencyEU, Horizon 2020, 644631
Available from: 2017-03-01 Created: 2017-03-01 Last updated: 2017-11-25
Huang, H., Karlsson, C., Strømme, M., Sjödin, M. & Gogoll, A. (2016). Hydroquinone–pyrrole dyads with varied linkers. Beilstein Journal of Organic Chemistry, 12, 89-96
Open this publication in new window or tab >>Hydroquinone–pyrrole dyads with varied linkers
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2016 (English)In: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 12, p. 89-96Article in journal (Refereed) Published
Abstract [en]

A series of pyrroles functionalized in the 3-position with p-dimethoxybenzene via various linkers (CH2, CH2CH2, CH=CH, C≡C) has been synthesized. Their electronic properties have been deduced from 1H NMR, 13C NMR, and UV–vis spectra to detect possible interactions between the two aromatic subunits. The extent of conjugation between the subunits is largely controlled by the nature of the linker, with the largest conjugation found with the trans-ethene linker and the weakest with the aliphatic linkers. DFT calculations revealed substantial changes in the HOMO–LUMO gap that correlated with the extent of conjugation found experimentally. The results of this work are expected to open up for use of the investigated compounds as components of redox-active materials in sustainable, organic electrical energy storage devices.

Keywords
conjugation, heterocycles, hydroquinone, linker effect, pyrrole
National Category
Organic Chemistry Engineering and Technology
Research subject
Chemistry with specialization in Organic Chemistry; Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-276440 (URN)10.3762/bjoc.12.10 (DOI)000368473900001 ()
Funder
Swedish Foundation for Strategic Research Carl Tryggers foundation Stiftelsen Olle Engkvist ByggmästareSweGRIDS - Swedish Centre for Smart Grids and Energy Storage
Available from: 2016-02-12 Created: 2016-02-12 Last updated: 2017-11-30Bibliographically approved
Karlsson, C., Nicholas, J., Evans, D., Forsyth, M., Strömme, M., Sjödin, M., . . . Pozo-Gonzalo, C. (2016). Stable Deep Doping of Vapor-Phase Polymerized Poly(3,4-ethylenedioxythiophene)/Ionic Liquid Supercapacitors.. ChemSusChem, 9(16), 2112-2121
Open this publication in new window or tab >>Stable Deep Doping of Vapor-Phase Polymerized Poly(3,4-ethylenedioxythiophene)/Ionic Liquid Supercapacitors.
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2016 (English)In: ChemSusChem, ISSN 1864-5631, E-ISSN 1864-564X, Vol. 9, no 16, p. 2112-2121Article in journal (Refereed) Published
Abstract [en]

Liquid-solution polymerization and vapor-phase polymerization (VPP) have been used to manufacture a series of chloride- and tosylate-doped poly(3,4-ethylenedioxythiophene) (PEDOT) carbon paper electrodes. The electrochemistry, specific capacitance, and specific charge were determined for single electrodes in 1-ethyl-3-methylimidazolium dicyanamide (emim dca) ionic liquid electrolyte. VPP-PEDOT exhibits outstanding properties with a specific capacitance higher than 300 F g(-1) , the highest value reported for a PEDOT-based conducting polymer, and doping levels as high as 0.7 charges per monomer were achieved. Furthermore, symmetric PEDOT supercapacitor cells with the emim dca electrolyte exhibited a high specific capacitance (76.4 F g(-1) ) and high specific energy (19.8 Wh kg(-1) ). A Ragone plot shows that the VPP-PEDOT cells combine the high specific power of conventional ("pure") capacitors with the high specific energy of batteries, a highly sought-after target for energy storage.

National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-299945 (URN)10.1002/cssc.201600333 (DOI)000383267600014 ()27325487 (PubMedID)
Funder
EU, Horizon 2020, 644631Stiftelsen Olle Engkvist ByggmästareSwedish Foundation for Strategic Research
Available from: 2016-07-31 Created: 2016-07-31 Last updated: 2017-11-28Bibliographically approved
Sjödin, M., Karlsson, C., Huang, H., Yang, L., Xiao, H., Strömme, M., . . . Gogoll, A. (2015). Design principles for constructing conducting redox polymer based battery materials. In: : . Paper presented at 249th ACS National Meeting & Exposition, March 22-26, 2015, Denver, CO, Chemistry of Natural Resources.
Open this publication in new window or tab >>Design principles for constructing conducting redox polymer based battery materials
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2015 (English)Conference paper, Oral presentation with published abstract (Refereed)
National Category
Physical Chemistry Engineering and Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-255226 (URN)
Conference
249th ACS National Meeting & Exposition, March 22-26, 2015, Denver, CO, Chemistry of Natural Resources
Available from: 2015-06-15 Created: 2015-06-15 Last updated: 2017-01-25
Karlsson, C., Huang, H., Strømme, M., Gogoll, A. & Sjödin, M. (2015). Impact of Linker in Polypyrrole/Quinone Conducting Redox Polymers. RSC Advances, 5(15), 11309-11316
Open this publication in new window or tab >>Impact of Linker in Polypyrrole/Quinone Conducting Redox Polymers
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2015 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 5, no 15, p. 11309-11316Article in journal (Refereed) Published
Abstract [en]

Organic conducting redox polymers are being investigated as the active component for secondary battery applications, as they have the potential to solve two of the main problems with small molecule-based organic electrodes for electrical energy storage, viz dissolution of the active compound in the electrolyte, and slow charge transport through the material. Herein we report the synthesis of a series of conducting redox polymers based on polypyrrole with hydroquinone pendant groups that are attached to the backbone via different linkers, and we investigate the impact of the linker on the interaction between the backbone and the pendant groups. For the directly linked polymer, oxidation of the pendant groups leads to a decrease of bipolaron absorbance, as well as a decrease in mass of the polymer film, both of which are reversible. The origin of these effects is discussed in light of the influence of the linker unit, electrolyte polarity, and electrolyte salt. For the longest linkers in the series, no interaction was observed, which was deemed the most beneficial situation for energy storage applications, as the energy storage capacity of the pendant groups can be utilized without disturbing the conductivity of the polymer backbone.

National Category
Physical Chemistry Engineering and Technology Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-230488 (URN)10.1039/c4ra15708g (DOI)000348986900057 ()
Available from: 2014-09-10 Created: 2014-08-26 Last updated: 2017-12-05
Karlsson, C., Huang, H., Strömme, M., Gogoll, A. & Sjödin, M. (2015). Ion- and Electron Transport in Pyrrole/Quinone Conducting Redox Polymers Investigated by In Situ Conductivity Methods. Electrochimica Acta, 179, 336-342
Open this publication in new window or tab >>Ion- and Electron Transport in Pyrrole/Quinone Conducting Redox Polymers Investigated by In Situ Conductivity Methods
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2015 (English)In: Electrochimica Acta, ISSN 0013-4686, E-ISSN 1873-3859, Vol. 179, p. 336-342Article in journal (Refereed) Published
Abstract [en]

Polypyrrole functionalized with redox active pendant groups constitutes a so called conducting redox polymer, and functions both as a conducting polymer and as a redox polymer. The electrochemical response reveals capacitive charging of the conducting backbone as well as redox cycling of the pendant groups. While the backbone provides an electrically conducting matrix for fast electron transport through the material, the pendant groups offer a large charge storage capacity, much greater than that of polypyrrole itself. We have investigated such polypyrrole-hydroquinone conducting redox polymers, with focus on their in situ conductivity during electrochemical cycling, in order to understand the charge transport mechanisms in this type of system. The most notable feature is that oxidation of the pendant groups leads to a large decrease in the polymer conductivity. The causes of this phenomenon are discussed, as well as the rate limitations of fast redox cycling of the polymer, which are investigated through a combination of bipotentiostat cyclic voltammetry and potential steps of polymer films on interdigitated array electrodes.

Keywords
In situ conductivity, conducting polymers, redox polymers, polypyrrole, rate limitations
National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-248597 (URN)10.1016/j.electacta.2015.02.193 (DOI)000362292200042 ()
Funder
Swedish Foundation for Strategic Research Carl Tryggers foundation Swedish Energy Agency
Available from: 2015-04-01 Created: 2015-04-01 Last updated: 2017-12-04Bibliographically approved
Sjödin, M., Karlsson, C., Huang, H., Strömme, M. & Sterby, M. (2015). Quinone Based Conducting Redox Polymers for Electrical Energy Storage. In: : . Paper presented at 10th International Frumkin Symposium on Electrochemistry.
Open this publication in new window or tab >>Quinone Based Conducting Redox Polymers for Electrical Energy Storage
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2015 (English)Conference paper, Oral presentation with published abstract (Refereed)
National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials; Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-267446 (URN)
Conference
10th International Frumkin Symposium on Electrochemistry
Available from: 2015-11-23 Created: 2015-11-23 Last updated: 2017-01-25
Hao, H., Karlsson, C., Strømme, M., Gogoll, A. & Sjödin, M. (2015). Quinone Based Polypyrroles for Energy Storage Materials. In: : . Paper presented at ISE 66th Annual Meeting.
Open this publication in new window or tab >>Quinone Based Polypyrroles for Energy Storage Materials
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2015 (English)Conference paper, Poster (with or without abstract) (Refereed)
National Category
Nano Technology
Identifiers
urn:nbn:se:uu:diva-269487 (URN)
Conference
ISE 66th Annual Meeting
Available from: 2015-12-16 Created: 2015-12-16 Last updated: 2017-01-25
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0003-2883-2696

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