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Reiersoelmoen, A. C., Csókás, D., Oeien-Oedegaard, S., Vanderkooy, A., Gupta, A. K., Carlsson, A.-C. C., . . . Erdélyi, M. (2020). Catalytic Activity of trans-Bis(pyridine)gold Complexes. Journal of the American Chemical Society, 6439-6446
Open this publication in new window or tab >>Catalytic Activity of trans-Bis(pyridine)gold Complexes
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2020 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, p. 6439-6446Article in journal (Refereed) Published
Abstract [en]

Gold catalysis has become one of the fastest growing fields in chemistry, providing new organic transformations and offering excellent chemoselectivities under mild reaction conditions. Methodological developments have been driven by wide applicability in the synthesis of complex structures, whereas the mechanistic understanding of Au(III)-mediated processes remains scanty and have become the Achilles’ heel of methodology development. Herein, the systematic investigation of the reactivity of bis(pyridine)-ligated Au(III) complexes is presented, based on NMR spectroscopic, X-ray crystallographic, and DFT data. The electron density of pyridines modulates the catalytic activity of Au(III) complexes in propargyl ester cyclopropanation of styrene. To avoid strain induced by a ligand with a nonoptimal nitrogen–nitrogen distance, bidentate bis(pyridine)–Au(III) complexes convert into dimers. For the first time, bis(pyridine)Au(I) complexes are shown to be catalytically active, with their reactivity being modulated by strain.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2020
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-409830 (URN)10.1021/jacs.0c01941 (DOI)
Funder
The Research Council of Norway
Available from: 2020-04-30 Created: 2020-04-30 Last updated: 2020-04-30
Kovacs, D., Kiraev, S., Phipps, D., Orthaber, A. & Borbas, K. E. (2020). Eu(III) and Tb(III) Complexes of Octa- and Nonadentate Macrocyclic Ligands Carrying Azide, Alkyne, and Ester Reactive Groups. Inorganic Chemistry, 59(1), 106-117
Open this publication in new window or tab >>Eu(III) and Tb(III) Complexes of Octa- and Nonadentate Macrocyclic Ligands Carrying Azide, Alkyne, and Ester Reactive Groups
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2020 (English)In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 59, no 1, p. 106-117Article in journal (Refereed) Published
Abstract [en]

Azide- and allcyne-functionalized bioconjugable luminescent lanthanide complexes are reported. Reactive handles were introduced into the complexes by the late-stage modification of a methylenecarboxylic acid antenna pendent group. Tb and Eu quantum yields (11-13% and 3.4-3.6%, respectively) were not greatly affected by the presence of the azide or the alkyne compared to the parent complex (Phi(Tb) = 10%, Phi(Eu) = 2.8%). Two avenues were explored for improving the luminescence of the lanthanide (Ln) complexes: (1) attaching the antenna through a tertiary amide linker and (2) replacing a monodentate carboxylate ligand with a bidentate pyridylcarboxylate donor, which yielded a nonadentate ligand that could saturate the lanthanide coordination sphere and eliminate the quenching metal-bound water molecule that was present in the octadentate complexes. The combination of both approaches yielded Eu and Tb emitters with 5.8% and 46% quantum yields. For the Eu complex, this value was the same as Phi(Eu) in the octadentate parent complex. We attribute this to increased photoinduced electron transfer quenching in the nonadentate species, which compensates for the reduced O-H quenching.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC, 2020
National Category
Inorganic Chemistry
Identifiers
urn:nbn:se:uu:diva-404694 (URN)10.1021/acs.inorgchem.9b01576 (DOI)000506719300011 ()31613593 (PubMedID)
Funder
Swedish Research Council, 201704077Knut and Alice Wallenberg Foundation, 2018.0066
Available from: 2020-02-27 Created: 2020-02-27 Last updated: 2020-03-25Bibliographically approved
Jafri, S. H., Hayat, A., Wallner, A., Sher, O., Orthaber, A., Ottosson, H. & Leifer, K. (2020). Nanomolecular electronic devices based on AuNP molecule nanoelectrodes using molecular place-exchange process. Nanotechnology, 31(22), Article ID 225207.
Open this publication in new window or tab >>Nanomolecular electronic devices based on AuNP molecule nanoelectrodes using molecular place-exchange process
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2020 (English)In: Nanotechnology, ISSN 0957-4484, E-ISSN 1361-6528, Vol. 31, no 22, article id 225207Article in journal (Refereed) Published
Abstract [en]

The implementation of electronics applications based on molecular electronics devices is hampered by the difficulty of placing a single or a few molecules with application-specific electronic properties in between metallic nanocontacts. Here, we present a novel method to fabricate 20 nm sized nanomolecular electronic devices (nanoMoED) using a molecular place-exchange process of nonconductive short alkyl thiolates with various short chain conductive oligomers. After the successful place-exchange with short-chain conjugated oligomers in the nanoMoED devices, a change in device resistance of up to four orders of magnitude for 4,4 '-biphenyldithiol (BPDT), and up to three orders of magnitude for oligo phenylene-ethynylene (OPE), were observed. The place-exchange process in nanoMoEDs are verified by measuring changes in device resistance during repetitive place-exchange processes between conductive and nonconductive molecules and surface-enhanced Raman spectroscopy. This opens vast possibilities for the fabrication and application of nanoMoED devices with a large variety of molecules.

Place, publisher, year, edition, pages
IOP PUBLISHING LTD, 2020
Keywords
nanoparticle-nanoelectrode platform, molecular electronics devices, short chain organic molecules, place exchange process
National Category
Biochemistry and Molecular Biology
Identifiers
urn:nbn:se:uu:diva-408925 (URN)10.1088/1361-6528/ab76e8 (DOI)000521469800001 ()32066129 (PubMedID)
Funder
Swedish Research CouncilKnut and Alice Wallenberg FoundationSwedish Energy AgencySwedish Foundation for Strategic Research Göran Gustafsson Foundation for Research in Natural Sciences and MedicineCarl Tryggers foundation
Note

De två första författarna delar förstaförfattarskapet.

Available from: 2020-04-26 Created: 2020-04-26 Last updated: 2020-04-26Bibliographically approved
Maeda, G., van der Wal, J., Gupta, A. K., Munissi, J. J. E., Orthaber, A., Sunnerhagen, P., . . . Erdélyi, M. (2020). Oxygenated Cyclohexene Derivatives and Other Constituents from the Roots of Monanthotaxis trichocarpa. Journal of Natural Products, 83(2), 210-215
Open this publication in new window or tab >>Oxygenated Cyclohexene Derivatives and Other Constituents from the Roots of Monanthotaxis trichocarpa
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2020 (English)In: Journal of Natural Products, ISSN 0163-3864, E-ISSN 1520-6025, Vol. 83, no 2, p. 210-215Article in journal (Refereed) Published
Abstract [en]

Three new oxygenated cyclohexene derivatives, trichocarpeols A (1), B (2), and C (3), along with nine known secondary metabolites, were isolated from the methanolic root extract of Monanthotaxis trichocarpa. They were identified by NMR spectroscopic and mass spectrometric analyses, and the structure of trichocarpeol A (1) was confirmed by single-crystal X-ray diffraction. Out of the 12 isolated natural products, uvaretin (4) showed activity against the Gram-positive bacterium Bacillus subtilis with a MIC value of 18 μM. None of the isolated metabolites was active against the Gram-negative Escherichia coli at a ∼5 mM (2000 μg/mL) concentration. Whereas 4 showed cytotoxicity at EC50 10.2 μM against the MCF-7 human breast cancer cell line, the other compounds were inactive or not tested.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2020
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-409742 (URN)10.1021/acs.jnatprod.9b00363 (DOI)
Funder
Swedish Research Council, 2016-05857
Available from: 2020-04-28 Created: 2020-04-28 Last updated: 2020-04-28
Wani, I. H., Jafri, S. H., Wärnå, J., Hayat, A., Li, H., Shukla, V. A., . . . Leifer, K. (2019). A sub 20 nm metal-conjugated molecule junction acting as a nitrogen dioxide sensor. Nanoscale, 11(14), 6571-6575
Open this publication in new window or tab >>A sub 20 nm metal-conjugated molecule junction acting as a nitrogen dioxide sensor
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2019 (English)In: Nanoscale, ISSN 2040-3364, E-ISSN 2040-3372, Vol. 11, no 14, p. 6571-6575Article in journal (Refereed) Published
Abstract [en]

The interaction of a gas molecule with a sensing material causes the highest change in the electronic structure of the latter, when this material consists of only a few atoms. If the sensing material consists of a short, conductive molecule, the sensing action can be furthermore probed by connecting such molecules to nanoelectrodes. Here, we report that NO2 molecules that adhere to 4,4'-biphenyldithiol (BPDT) bound to Au surfaces lead to a change of the electrical transmission of the BPDT. The related device shows reproducible, stable measurements and is so far the smallest (<20 nm) gas sensor. It demonstrates modulation of charge transport through molecules upon exposure to nitrogen dioxide down to concentrations of 55 ppb. We have evaluated several devices and exposure conditions and obtained a close to linear dependence of the sensor response on the gas concentration.

National Category
Nano Technology
Identifiers
urn:nbn:se:uu:diva-381056 (URN)10.1039/c8nr08417c (DOI)000464454400007 ()30916070 (PubMedID)
Funder
Swedish Research CouncilKnut and Alice Wallenberg FoundationGöran Gustafsson Foundation for Research in Natural Sciences and MedicineCarl Tryggers foundation Swedish Energy AgencySwedish Foundation for Strategic Research
Available from: 2019-04-03 Created: 2019-04-03 Last updated: 2019-05-03Bibliographically approved
Orthaber, A. (2019). Andreas Orthaber. European Journal of Inorganic Chemistry (11-12), 1441-1442
Open this publication in new window or tab >>Andreas Orthaber
2019 (English)In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 11-12, p. 1441-1442Article in journal, Editorial material (Other academic) Published
Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH, 2019
National Category
Inorganic Chemistry
Identifiers
urn:nbn:se:uu:diva-382022 (URN)10.1002/ejic.201900194 (DOI)000462351000003 ()
Available from: 2019-04-23 Created: 2019-04-23 Last updated: 2019-04-23Bibliographically approved
Devaraj, K., Ingner, F., Sollert, C., Gates, P. J., Orthaber, A. & Pilarski, L. T. (2019). Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation. Journal of Organic Chemistry, 84(9), 5863-5871
Open this publication in new window or tab >>Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation
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2019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 9, p. 5863-5871Article in journal (Refereed) Published
Abstract [en]

A new, operationally simple approach is presented to access arynes and their fluoride-activated precursors based on Ru-catalyzed C-H silylation of arylboronates. Chromatographic purification may be deferred until after aryne capture, rendering the arylboronates de facto precursors. Access to various new arynes and their derivatives is demonstrated, including, for the first time, those based on a 2,3-carbazolyne and 2,3-fluorenyne core, which pave the way for novel derivatizations of motifs relevant to materials chemistry.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC, 2019
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-387960 (URN)10.1021/acs.joc.9b00221 (DOI)000467319600089 ()30835118 (PubMedID)
Funder
Swedish Research CouncilCarl Tryggers foundation
Available from: 2019-06-27 Created: 2019-06-27 Last updated: 2019-06-27Bibliographically approved
Green, J. P., Gupta, A. K. & Orthaber, A. (2019). Effect of Arsenic Coordination State on the Structure, Aromaticity, and Optical Properties of Dithieno[3,2-b:2 ',3 '-d]arsoles. European Journal of Inorganic Chemistry (11-12), 1539-1543
Open this publication in new window or tab >>Effect of Arsenic Coordination State on the Structure, Aromaticity, and Optical Properties of Dithieno[3,2-b:2 ',3 '-d]arsoles
2019 (English)In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 11-12, p. 1539-1543Article in journal (Refereed) Published
Abstract [en]

A silylated derivative of 4-phenyl-dithieno[3,2-b:2 ',3 '-d]arsole (DTAs) was synthesized, and the effect of coordinating of DTAs compounds to Pd on their structural and optical properties was investigated. Coordination of the As to Pd was found to increase the structural aromaticity of the ring system as measured by the harmonic oscillator measure of heterocyclic electron delocalization (HOMHED), and the pyramidalization of the As atoms was also found to show a good correlation with the HOMHED values. However, coordination had a more subtle impact on the optical properties than seen for phosphorus-containing analogues as the metal-ligand interactions were weaker.

Keywords
Dithienoarsole, Aromaticity, Luminescence, Palladium complex, Arsenic
National Category
Inorganic Chemistry
Identifiers
urn:nbn:se:uu:diva-381571 (URN)10.1002/ejic.201801169 (DOI)000462351000012 ()
Funder
Swedish Research CouncilSwedish Energy AgencyCarl Tryggers foundation
Note

Correction in: Eur. J. Inorg. Chem. 2019, 1706

DOI: 10.1002/ejic.201900057

Available from: 2019-04-12 Created: 2019-04-12 Last updated: 2019-04-23Bibliographically approved
Pammer, F., Schepper, J., Gloeckler, J., Sun, Y. & Orthaber, A. (2019). Expansion of the scope of alkylboryl-bridged N -> B-ladder boranes: new substituents and alternative substrates. Dalton Transactions, 48(27), 10298-10312
Open this publication in new window or tab >>Expansion of the scope of alkylboryl-bridged N -> B-ladder boranes: new substituents and alternative substrates
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2019 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 48, no 27, p. 10298-10312Article in journal (Refereed) Published
Abstract [en]

A series of new boranes capable of forming intramolecular N -> B-heterocycles has been prepared and their properties have been studied by electrochemical methods and UV-vis-spectroscopy complemented by DFT calculations. A dimethylborane (BMe2), haloborane derivatives (BBr2, BF2, BI2) and mixed cyano/isocyano-borane (B(CN)(NC)) have been prepared by different techniques. Furthermore, 2 '-alkynyl-substituted 2-phenylpyridines bearing terminal tert-butyl- and trimethylsilyl-groups are introduced as a new class of substrates for hydroboration. Successful hydroboration with either 9H-borabicyclo[3.3.1]-nonane (9H-BBN), dimesitylborane (Mes(2)B-H), or Piers' borane ((C6F5)(2)B-H, BPF-H) furnished new pi-extended boranes capable of forming intramolecular six- or seven-membered N -> B-heterocycles (tBuBBN, SiBPF), and, in the case of Mes(2)BH, formation of a sterically crowded styrylborane (SiBMes(2)) incapable of intramolecular N -> B-coordination was observed. All the boranes listed above except BMe2 have been structurally characterized, and a study of their electrochemical properties showed that the systematic variation of the substituents on boron allows for the incremental variation of the electron affinity of the phenylpyridine-model system over a total range of >0.7 eV between alkylboranes (BMe2, BBN) and B(CN)(NC). B(CN)(NC) shows the strongest N -> B-bond (approximate to 175 kJ mol(-1)), and highest electron-affinity observed so far, and is the first example of a borane bearing an isocyano-substituent on boron.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY, 2019
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-391376 (URN)10.1039/c9dt01555h (DOI)000475742900042 ()31210241 (PubMedID)
Available from: 2019-09-03 Created: 2019-09-03 Last updated: 2019-09-03Bibliographically approved
Gupta, A. K. & Orthaber, A. (2019). Facile synthesis of silver alkynide cluster and coordination polymers using picolinic acid as a co-ligand. Dalton Transactions, 48(44), 16518-16524
Open this publication in new window or tab >>Facile synthesis of silver alkynide cluster and coordination polymers using picolinic acid as a co-ligand
2019 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 48, no 44, p. 16518-16524Article in journal (Refereed) Published
Abstract [en]

We describe five 1D-coordination polymers and two discrete silver clusters consisting of alkynides and picolinic carboxylates as co-ligands. In some cases, DMSO or EtOH further solvated the structural motifs. Utilising the sterically demanding tri-isopropylsilyl acetylene afforded a tridecanuclear cluster that possessed an unprecedented core with a silver center surrounded by six octahedrally arranged silver atoms.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY, 2019
National Category
Inorganic Chemistry
Identifiers
urn:nbn:se:uu:diva-398424 (URN)10.1039/c9dt03697k (DOI)000496535000035 ()31663564 (PubMedID)
Funder
Stiftelsen Olle Engkvist ByggmästareSwedish Research Council
Available from: 2019-12-06 Created: 2019-12-06 Last updated: 2019-12-06Bibliographically approved
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ORCID iD: ORCID iD iconorcid.org/0000-0001-5403-9902

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