PriOSS – Prinzipien oberflächengestützter Synthesestrategien, LOEWE Schwerpunkt
Organic nanostructures can be utilized in electronics devices such as microchips or in next-generation quantum computers. The properties of such functional molecular materials can be controlled by their dimensions and precise atomic structure. Lately, it was discovered that these functional nanostructures can be built very successfully on surfaces, a strategy denoted as “on-surface synthesis”. However, in contrast to the well-established solution-based synthesis, which has been applied for over 200 years, on-surface synthesis is still in its infancy. The objective of the LOEWE focus group PriOSS is to develop fundamental strategies of on-surface synthesis and to provide a toolset for this new method.
PriOSS
- Welcome to PriOSS
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Organic nanostructures can be utilized in electronics devices such as microchips or in next-generation quantum computers. The properties of such functional molecular materials can be controlled by their dimensions and precise atomic structure. Lately, it was discovered that these functional nanostructures can be built very successfully on surfaces, a strategy denoted as “on-surface synthesis”. However, in contrast to the well-established solution-based synthesis, which has been applied for over 200 years, on-surface synthesis is still in its infancy. The objective of the LOEWE focus group is to develop fundamental strategies of on-surface synthesis and to provide a toolset for this new method.
- PriOSS partners
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Funding
Networking
- PriOSS contact
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c/o Dr. Daniel Ebeling
Welcome to PriOSS
Organic nanostructures can be utilized in electronics devices such as microchips or in next-generation quantum computers. The properties of such functional molecular materials can be controlled by their dimensions and precise atomic structure. Lately, it was discovered that these functional nanostructures can be built very successfully on surfaces, a strategy denoted as “on-surface synthesis”. However, in contrast to the well-established solution-based synthesis, which has been applied for over 200 years, on-surface synthesis is still in its infancy. The objective of the LOEWE focus group is to develop fundamental strategies of on-surface synthesis and to provide a toolset for this new method.
News
10/2022 "ERC Synergy Grant for PriOSS chemist Michael Gottfried"
European Research Council funds search for unusual ring-shaped carbon compounds for applications in organic electronics
Prof. Dr. Michael Gottfried from the University of Marburg has received an ERC Synergy Grant from the European Research Council (ERC) together with Prof. Dr. Michael Mastalerz from the University of Heidelberg and Prof. Dr. Holger Bettinger from the University of Tübingen. With their project "Tackling the Cyclacene Challenge" (TACY), the three researchers are pursuing the goal of generating a special class of ring-shaped carbon compounds - the cyclacenes - for the first time. The European Research Council is funding the project with around 11 million euros. Of this, around 4.5 million euros is earmarked for the research work at Philipps-Universität Marburg.
04/2022 "A deep look into the molecule"
Original Publication
Daniel Martin-Jimenez, Michael G. Ruppert, Alexander Ihle, Sebastian Ahles, Hermann A. Wegner, André Schirmeisen and Daniel Ebeling. "Chemical bond imaging using torsional and flexural higher eigenmodes of qPlus sensors." Nanoscale 14, 5329, 2022 (Cover Article). https://doi.org/10.1039/D2NR01062C
04/2022 "Organic chemistry under extreme conditions: Prof. Peter R. Schreiner receives ERC Advanced Grant"
Top researcher at the Institute of Organic Chemistry at the University of Giessen awarded the most important European funding prize - 2.5 million euros for the next five years
09/2021 "Handmade Nanoarchitectures"
In a recent paper in Nature Chemistry we show how to build nanostructures using individual organic molecules one by one with an atomic force microscope. This opens the path to prototyping of new molecular structures, otherwise impossible to fabricate.
Original Publication
Q. Zhong, A. Ihle, S. Ahlers, H.A. Wegner, A. Schirmeisen, D. Ebeling. "Constructing covalent organic nanoarchitectures molecule by molecule via scanning probe manipulation" Nature Chemistry, 2021
Publications
2022
- J. Martinez-Castro, R. Bolat, Q. Fan, S. Werner, H. H. Arefi, T. Esat, J. Sundermeyer, C. Wagner, J. Michael Gottfried, R. Temirov, M. Ternes, F. Stefan Tautz, Disentangling the electronic structure of an adsorbed graphene nanoring by scanning tunneling microscopy. Communications Materials 3, 57 (2022). DOI: https://doi.org/10.1038/s43246-022-00275-x
- B. P. Klein, A. Ihle, S. R. Kachel, L. Ruppenthal, S. J. Hall, L. Sattler, S. M. Weber, J. Herritsch, A. Jaegermann, D. Ebeling, R. J. Maurer, G. Hilt, R. Tonner-Zech, A. Schirmeisen, J. M. Gottfried, Topological Stone–Wales Defects Enhance Bonding and Electronic Coupling at the Graphene/Metal Interface. ACS Nano 16, 11979-11987 (2022). DOI: https://doi.org/10.1021/acsnano.2c01952
- A. Haags, X. Yang, L. Egger, D. Brandstetter, H. Kirschner, F. C. Bocquet, G. Koller, A. Gottwald, M. Richter, J. M. Gottfried, M. G. Ramsey, P. Puschnig, S. Soubatch, F. S. Tautz, Momentum space imaging of σ orbitals for chemical analysis. Sci Adv 8, eabn0819 (2022). DOI: https://doi.org/10.1126/sciadv.abn0819
- M. Denk, E. Speiser, J. Plaickner, S. Chandola, S. Sanna, P. Zeppenfeld, N. Esser, Surface Resonant Raman Scattering from Cu(110). Physical Review Letters 128, 216101 (2022). DOI: https://doi.org/10.1103/PhysRevLett.128.216101
- J.-N. Luy, P. Henkel, D. Grigjanis, J. Jung, D. Mollenhauer, R. Tonner-Zech, Bonding character of intermediates in on-surface Ullmann reactions revealed with energy decomposition analysis. Journal of Computational Chemistry, (2022). DOI: https://doi.org/10.1002/jcc.26855
- D. Martin-Jimenez, M. G. Ruppert, A. Ihle, S. Ahles, H. A. Wegner, A. Schirmeisen, D. Ebeling, Chemical bond imaging using torsional and flexural higher eigenmodes of qPlus sensors. Nanoscale 14, 5329-5339 (2022). DOI: https://doi.org/10.1039/D2NR01062C
- M. G. Ruppert, D. Martin-Jimenez, Y. K. Yong, A. Ihle, A. Schirmeisen, A. J. Fleming, D. Ebeling, Experimental analysis of tip vibrations at higher eigenmodes of QPlus sensors for atomic force microscopy. Nanotechnology 33, 185503 (2022). DOI: https://doi.org/10.1088/1361-6528/ac4759
2021
- Q. Zhong, A. Ihle, S. Ahles, H. A. Wegner, A. Schirmeisen, D. Ebeling, Constructing covalent organic nanoarchitectures molecule by molecule via scanning probe manipulation. Nature Chemistry, 1133–1139 (2021). DOI: https://doi.org/10.1038/s41557-021-00773-4
- Q. Fan, L. Yan, M. W. Tripp, O. Krejčí, S. Dimosthenous, S. R. Kachel, M. Chen, A. S. Foster, U. Koert, P. Liljeroth, J. M. Gottfried, Biphenylene network: A nonbenzenoid carbon allotrope. Science 372, 852-856 (2021). DOI: https://doi.org/10.1126/science.abg4509
- P. Liu, X.-Y. Chen, J. Cao, L. Ruppenthal, J. M. Gottfried, K. Müllen, X.-Y. Wang, Revisiting Acepleiadylene: Two-Step Synthesis and π-Extension toward Nonbenzenoid Nanographene. Journal of the American Chemical Society 143, 5314-5318 (2021). DOI: https://doi.org/10.1021/jacs.1c01826
- S. Werner, T. Vollgraff, J. Sundermeyer, Access to functionalized Pyrenes, Peropyrenes, Terropyrenes and Quarterropyrenes via Reductive Aromatization. Angewandte Chemie International Edition 60, 13631-13635 (2021). DOI: https://doi.org/10.1002/anie.202100686
- S. Werner, T. Vollgraff, J. Sundermeyer, Rylene- and diaza-rylene-derived cobalt clusters for solid-state pyrolysis towards undoped and N-doped carbon nanoparticles. Dalton Transactions 50, 14374-14383 (2021). DOI: https://doi.org/10.1039/D1DT02276H
- S. Werner, J. Sundermeyer, Synthesis of Unsymmetrically Functionalized Violanthrenes by Reductive Aromatization of Violanthrone Synlett 32, 1855-1860 (2021). DOI: https://doi.org/10.1055/a-1628-5664
- P.-M. Dombrowski, S. R. Kachel, L. Neuhaus, J. M. Gottfried, G. Witte, Temperature-programmed desorption of large molecules: influence of thin film structure and origin of intermolecular repulsion. Nanoscale 13, 13816-13826 (2021). DOI: https://doi.org/10.1039/D1NR03532K
- J. Herritsch, S. R. Kachel, Q. Fan, M. Hutter, L. J. Heuplick, F. Münster, J. M. Gottfried, On-surface porphyrin transmetalation with Pb/Cu redox exchange. Nanoscale 13, 13241-13248 (2021). DOI: https://doi.org/10.1039/D1NR04180K
- S. Werner, T. Vollgraff, Q. Fan, K. Bania, J. M. Gottfried, J. Sundermeyer, Reductive O-triflylation of naphthalene diimide: access to alkyne- and amine-functionalized 2,7-diazapyrenes. Organic Chemistry Frontiers 8, 5013-5023 (2021). DOI: https://doi.org/10.1039/D1QO00862E
- A. Adamkiewicz, T. Bohamud, M. Reutzel, U. Höfer, M. Dürr, Tip-induced β -hydrogen dissociation in an alkyl group bound on Si(001). Journal of Physics: Condensed Matter 33, 344004 (2021). DOI: https://doi.org/10.1088/1361-648x/ac0a1c
- E. Baal, M. Klein, K. Harms, J. Sundermeyer, 2,9-Diazadibenzoperylene and 2,9-Dimethyldibenzoperylene-1,3,8,10-tetratriflates: Key to Functionalized 2,9-Diazaperopyrenes. Chemistry – A European Journal 27, 12610-12618 (2021). DOI: https://doi.org/10.1002/chem.202101719
- S. Werner, T. Vollgraff, J. Sundermeyer, Tetrasubstituted Peropyrenes Formed by Reductive Aromatization: Synthesis, Functionalization and Characterization. Chemistry – A European Journal 27, 11065-11075 (2021). DOI: https://doi.org/10.1002/chem.202101101
- B. P. Klein, L. Ruppenthal, S. J. Hall, L. E. Sattler, S. M. Weber, J. Herritsch, A. Jaegermann, R. J. Maurer, G. Hilt, J. M. Gottfried, Topology Effects in Molecular Organic Electronic Materials: Pyrene and Azupyrene*. ChemPhysChem 22, 1065-1073 (2021). DOI: https://doi.org/10.1002/cphc.202100222
- T. Glaser, J. Meinecke, L. Freund, C. Länger, J.-N. Luy, R. Tonner, U. Koert, M. Dürr, Click Chemistry in Ultra-high Vacuum – Tetrazine Coupling with Methyl Enol Ether Covalently Linked to Si(001). Chemistry – A European Journal 27, 8082-8087 (2021). DOI: https://doi.org/10.1002/chem.202005371
- K. Feng, E. Solel, P. R. Schreiner, H. Fuchs, H.-Y. Gao, Diamantanethiols on Metal Surfaces: Spatial Configurations, Bond Dissociations, and Polymerization. The Journal of Physical Chemistry Letters 12, 3468-3475 (2021). DOI: https://doi.org/10.1021/acs.jpclett.1c00387
- T. Glaser, J. Meinecke, C. Länger, J. Heep, U. Koert, M. Dürr, Solution-Based Alkyne–Azide Coupling on Functionalized Si(001) Prepared under UHV Conditions. The Journal of Physical Chemistry C 125, 4021-4026 (2021). DOI: https://doi.org/10.1021/acs.jpcc.0c11353
- S. R. Kachel, P.-M. Dombrowski, T. Breuer, J. M. Gottfried, G. Witte, Engineering of TMDC–OSC hybrid interfaces: the thermodynamics of unitary and mixed acene monolayers on MoS2. Chemical Science 12, 2575-2585 (2021). DOI: https://doi.org/10.1039/D0SC05633B
- T. Glaser, J. Meinecke, C. Länger, J.-N. Luy, R. Tonner, U. Koert, M. Dürr, Combined XPS and DFT investigation of the adsorption modes of methyl enol ether functionalized cyclooctyne on Si(001). ChemPhysChem 22, 404-409 (2021). DOI: https://doi.org/10.1002/cphc.202000870
- E. Geringer, M. Gerhard, M. Koch, C. K. Krug, J. M. Gottfried, S. Dehnen, Pyrene-Terminated Tin Sulfide Clusters: Optical Properties and Deposition on a Metal Surface. Chemistry – A European Journal 27, 2734-2741 (2021). DOI: https://doi.org/10.1002/chem.202003889
Principle Investigators
Principal Investigators
Prof. Dr. André Schirmeisen
Institute of Applied Physics (IAP)
Justus-Liebig University Giessen
Heinrich-Buff-Ring 16
35392 Giessen, Germany
Secretariat:
+49 641 99 33411
Email:
Homepage:
PriOSS Expertise
Within PriOSS we are using and further developing a powerful microscopy technique allowing us to image every single bond of an organic molecule. This is done at very low temperatures close to absolute zero, in order freeze any unwanted motion while imaging. Not only the molecular structure is visualized but even intricate properties like molecular chirality. In between those photographic snapshots the surface is heated, and the thermal energy induces chemical reactions between the molecules, resembling the 2D analogy to traditional in-liquid synthesis. This is termed 2D chemistry and obeys completely different reaction laws, eventually leading to new synthesis strategies. Additionally, we have employed this atomic force microscope to induce reactions between several surface molecules even at cryogenic temperatures by applying voltage pulses. This enables us to create new molecular structures, so far impossible to synthesize.
Prof. Dr. Michael Dürr
Institute of Applied Physics (IAP)
Justus-Liebig University Giessen
Heinrich-Buff-Ring 16
35392 Giessen, Germany
Phone:
+49 641 99 33490
Secretariat:
+49 641 99 33411
Email:
PriOSS Expertise
Surface analytical tools for the investigation of the kinetics and dynamics of surface reactions: Variable temperature scanning tunneling microscopy, (in-situ) photoelectron spectroscopy, surface sensitive mass spectrometry.
Institute for Organic Chemistry
Justus-Liebig University Giessen
Heinrich-Buff-Ring 17
35392 Giessen, Germany
Phone:
+49 641 99 34330
Fax:
+49 641 99 34349
Secretariat:
+49 641 99 34341
Email:
Department of Chemistry, Physical Chemistry
Philipps-University Marburg
Hans-Meerwein-Str.
35032 Marburg, Germany
Phone:
+49 6421 2822541
Fax:
+49 6421 2822542
Email:
Department of Chemistry
Philipps-University Marburg
Hans-Meerwein-Str. 4
35032 Marburg, Germany
Phone:
+49 6421 28 25693
Fax:
+49 6421 28 25711
Secretariat:
+49 6421 28 25669
Email:
Institute for Organic Chemistry
Justus-Liebig University Giessen
Heinrich-Buff-Ring 17
35392 Giessen, Germany
Phone:
+49 641 99 34300
Fax:
+49 641 99 34309
Secretariat:
+49 99 34301
Email:
Institute of Physical Chemistry
Justus-Liebig University Giessen
Heinrich-Buff-Ring 17
35392 Giessen, Germany
Phone:
+49 641 99 34560
Fax:
+49 641 99 34509
Secretariat:
+49 641 99 34551
Email:
Institute for Theoretical Physics
Justus-Liebig University Giessen
Heinrich-Buff-Ring 16
35392 Giessen, Germany
Phone:
+49 641 99 33362
Fax:
+49 641 99 33369
Secretariat:
+49 641 99 33361
Email:
PriOSS Symposium
In Ebsdorfergrund - just under a 30-minute drive from Giessen - lies Rauischholzhausen Castle, probably the most beautiful estate at JLU. Congresses, workshops, seminars and also festivals are held here on a regular basis. The estate, built at the end of the 19th century, looks like a fairy-tale castle, nestled in a spacious park in the style of English landscape gardens.
About the conference venue Rauischholzhausen Castle
Travel via public transport:
- The nearest DB train station is Marburg Hbf, which is on the main DB line Frankfurt-Gießen-Kassel and is served by local, RE and IC trains about every hour.
- According to the Deutsche Bahn timetable information, a bus of line 80 departs from Marburg (Lahn) Südbahnhof to Rauischholzhausen. Departure 12:09, 12:41, 13:41, 14:19 or 17:09, 18:19, 19:09; low-floor bus direction Stadtallenallendorf-Schweinsberg, arrival in Rauischholzhausen (Potsdamer Straße) about 30 minutes later.
- This bus only runs Monday-Friday.
- For more information on how to get from Frankfurt (Main) Flughafen Regionalbahnhof to Ebsdorfergrund-Rauischholzhausen Potsdamer Straße please visit www.rmv.de
Travel via Taxi
- Taxis from Marburg station to Rauischholzhausen Castle take about 25 minutes and cost about 25€*
- For taxi companies based in Marburg please consult www.gelbeseiten.de
*prices without guarantee
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Ullmann coupling mechanism
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Molecule by molecule creation of covalent organic nanoarchitectures by scanning probe manipulation.
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Reaction of two individual organic molecules on a surface with an atomic force microscope.
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news22-04
Low-temperature atomic force microscopy and CO-functionalized tips can be used to visualize the chemical structure of individual molecules. By exciting a torsional vibration mode (twisting along the longitudinal axis) of the sensor, a particularly high image contrast is obtained. Graphic: Miriam Ebeling and Daniel Ebeling
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Marburg surface and nano researcher Prof. Dr. Michael Gottfried in his laboratory. Photo: Jan Hosan
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Reaction of two individual organic molecules on a surface with an atomic force microscope.
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