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Synthesis of Organic Building Blocks for Internal Interfaces

DNTT and Pentacene Derivatives

Novel fluoro-substituted pentacene and DNTT derivatives are synthesized and their packing motifs are characterized by X-ray analysis. Organic-[inorganic] interfaces prepared from tailored thin films are characterized regarding their electronic behavior to get detailed insight into resulting semiconductor properties in respect to the chemical structure.
Foto: Philipp Reiß
Covalent Attachment of Organic Builiding Blocks on Si(001)

Well-ordered multilayers are generated on Si(001) employing the chemoselective [2+2] cycloaddition of functionalized cyclooctynes with silicon dangling bonds. Development of novel, efficient and orthogonal cyclooctyne based synthetic strategies is our interest. The introduction of bifunctional cyclooctynes to the Si(001) surface enables layerwise construction of organic multilayers. In addition, reactions on Si(001) for example ether cleavage via datively bonded intermediate are investigated to allow a more general description of Si(001) reactivity.
Foto: Philipp Reiß

Related Publications:

  1. 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", J. Phys. Chem. C 2021, accepted.
  2. M. W. Tripp, D. Bischof, M. Dreher, G. Witte, U. Koert "Synthesis and Molecular Properties of Partially Fluorinated DNTTs", Eur. J. Org. Chem 2021, accepted.
  3. 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, 2020, accepted.
  4. T. Glaser, C. Länger, J. Heep, J. Meinecke, M. G. Silly, U. Koert, M. Dürr, "Starting from a Fixed Geometry: Real-Time XPS Investigation of a Surface Reaction with Controlled Molecular Configurations", J. Phys. Chem. C, 2020, 124, 22619-22624.
  5. M. W. Tripp, U. Koert, "Synthesis of 6,13-difluoropentacene", Beilstein J. Org. Chem., 2020, 16, 2136 - 2140.
  6. P. E. Hofmann, M. W. Tripp, D. Bischof, Y. Grell, A. L. C. Schiller, T. Breuer, S. I. Ivlev, G. Witte, U. Koert "Unilaterally Fluorinated Acenes: Synthesis and Solid State Properties", Angew. Chem., 2020, 59, 16501–16505.
  7. J. Heep, J.-N. Luy, C. Länger, J. Meinecke, U. Koert, R. Tonner, M. Dürr "Adsorption of Methyl-Substituted Benzylazide on Si(001) - Reaction Channels and Final Configurations" , J. Phys. Chem. C, 2020, 124, 18, 9940-9946.
  8. C. Länger, J. Heep, P. Nikodemiak, T. Bohamud, P. Kirsten, U. Höfer, U. Koert, M. Dürr, "Formation of Si/organic interfaces using alkyne-functionalized cyclooctynes - precursor-mediated adsorption of linear alkynes versus direct adsorption of cyclooctyne on Si(001)", J. Phys. Condens. Matter, 2019, 31, 034001.
  9. J. Meinecke, U. Koert, "Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach", Org. Lett., 2019, 21, 7609-7612.
  10. G. Mette, A. Adamkiewicz, M. Reutzel, U. Koert, M. Dürr, U. Höfer "Controlling an SN2 Reaction by Electronic and Vibrational Excitation: Tip-Induced Ether Cleavage on Si(001)", Angew. Chem., 2019, 58, 3417-3420.
  11. Länger, J. Heep, P. Nikodemiak, T. Bohamud, P. Kirsten, U. Höfer, U. Koert, M. Dürr, "Formation of Si/organic interfaces using alkyne-functionalized cyclooctynes - precursor-mediated adsorption of linear alkynes versus direct adsorption of cyclooctyne on Si(001)", J. Phys. Condens. Matter, 2019,  31, 034001.
  12. Reutzel, N. Münster, M. Lipponer, C. Länger, U. Hoefer, U. Koert, M. Dürr, "Chemoselective Reactivity of Bifunctional Cyclooctynes on Si(001)", J. Phys. Chem. C,2016, 26284-26289.
  13. Münster, P. Nikodemiak, U. Koert, "Chemoselective Layer-by-Layer Approach Utilizing Click Reactions with Ethynylcyclooctynes and Diazides", Org. Lett.2016, 18, 4296-4299.
  14. Reutzel, G. Mette, P. Stromberger, U. Koert, M. Dürr, U. Höfer "Dissociative Adsorption of Diethyl Ether on Si(001) Studied by means of Scanning Tunneling Microscopy and Photoelectron Spectroscopy", J. Phys. Chem. C2015, 119, 6018-6023.
  15. Schwaben, N. Münster, M. Klues, T. Breuer, P. Hofmann, K. Harms, G. Witte, U. Koert, "Efficient Syntheses of Novel Fluoro-Substituted Pentacenes and Azapentacenes: Molecular and Solid-State Properties", Chem. Eur. J.2015, 13751-13771.