Generation of N->B-Ladder-type Structures via Cycloaddition Reactions

• Applicant: Professor Dr. Peter Bäuerle, since 10/2020
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation ; Physical Chemistry of Molecules, Liquids and Interfaces, Biophysical Chemistry ; Preparatory and Physical Chemistry of Polymers
• Term: from 2016 to 2021
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 320261689

• Final Report Year: 2021

Final Report Abstract

We have realized almost all reactions proposed in the original proposal and have made a broad range of new, chemically diverse target structures accessible. The target boranes discussed were all fully characterized (1H, 13C, 11B, (19F) NMR, HRMS or elemental analysis, UV-vis absorption and fluorescence spectroscopy). Some envisioned outcomes of the project proved more challenging than expected. Still, the trove of highly diverse results on most of the addressed topics will allow us to complete several publications and new triazole-, tetrazole and oxadiazole-based boranes in the coming months. Furthermore, we have made significant inroads into the challenging chemistry fluoromesityl- (FMes) functionalized boranes. The results of this project lay a broad foundation for the further exploration of this synthetic strategy, in the development of organic n-type materials and for its exploitation in the high-throughput screening of borane-based Chemosensors.

Publications

• “Tuning of Electronic Properties via Labile N→B-Coordination in Conjugated Organoboranes”, J. Mater. Chem. C. 2017, 5, 1730–1741
  S. Schraff, Y. Sun, F. Pammer
  (See online at https://doi.org/10.1039/C6TC05418H)
• “Asymmetric Chain-growth Synthesis of Polyisocyanide with Chiral Nickel Pre-Catalysts”, J. Polym. Sci. A: Polym. Chem. 2020, 58, 2221-2233
  S. Schraff, N. M. Kreienborg, J. Trampert, Y. Sun, A. Orthaber, C. Merten, F. Pammer
  (See online at https://doi.org/10.1002/pol.20200153)
• “Electronic Properties and Solid-State Packing of Isocyanofulvenes, and Their Gold(I) Chloride Complexes”, Inorg. Chem. 2020, 59, 17171-17183
  S. Schraff, J. Trampert, A. Orthaber, F. Pammer
  (See online at https://doi.org/10.1021/acs.inorgchem.0c02435)
• “Turn-on Fluorescence Sensors Based on Dynamic Intramolecular N→B-Coordination”, Org. Chem. Front. 2020, 7, 1437-1452
  R. Koch, Y. Sun, A. Orthaber, A. J. Pierik, F. Pammer
  (See online at https://doi.org/10.1039/D0QO00267D)