Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine

Jean Garnier, Alan R. Kennedy, Leonard E. A. Berlouis, Andrew T. Turner and John A. Murphy
Beilstein J. Org. Chem. 2010, 6, No. 73. https://doi.org/10.3762/bjoc.6.73

Supporting Information

Supporting Information features detailed information on experimental procedures and compound characterisation.

Supporting Information File 1: Experimental Part
Format: PDF Size: 256.2 KB Download

Cite the Following Article

Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine
Jean Garnier, Alan R. Kennedy, Leonard E. A. Berlouis, Andrew T. Turner and John A. Murphy
Beilstein J. Org. Chem. 2010, 6, No. 73. https://doi.org/10.3762/bjoc.6.73

How to Cite

Garnier, J.; Kennedy, A. R.; Berlouis, L. E. A.; Turner, A. T.; Murphy, J. A. Beilstein J. Org. Chem. 2010, 6, No. 73. doi:10.3762/bjoc.6.73

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Franzen, J. H.; Wilm, L. F. B.; Rotering, P.; Wurst, K.; Seidl, M.; Dielmann, F. Electron-rich pyridines with para-N-heterocyclic imine substituents: ligand properties and coordination to CO2, SO2, BCl3 and PdII complexes. Dalton transactions (Cambridge, England : 2003) 2024, 53, 11876–11883. doi:10.1039/d4dt01399a
  • Khor, C. K.; Calhoun, L. A.; Neville, J. J.; Dyker, C. A. Experimental and Theoretical Predictors for Redox Potentials of Bispyridinylidene Electron Donors. Chemphyschem : a European journal of chemical physics and physical chemistry 2024, 25, e202400092. doi:10.1002/cphc.202400092
  • Jiang, S.; Wang, W.; Mou, C.; Zou, J.; Jin, Z.; Hao, G.; Chi, Y. R. Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors. Nature communications 2023, 14, 7381. doi:10.1038/s41467-023-43198-y
  • Li, Y.; Ye, J.-J.; Medjahed, A.; Aldakov, D.; Pouget, S.; Djurado, E.; Xu, L.; Reiss, P. High Fill Factor and Reduced Hysteresis Perovskite Solar Cells Using Small-Molecule-Engineered Nickel Oxide as the Hole Transport Layer. ACS Applied Energy Materials 2023, 6, 1555–1564. doi:10.1021/acsaem.2c03434
  • Chi, Y. R.; Jiang, S.; Wang, W.; Mou, C.; Zou, J.; Jin, Z.; Hao, G.-F. Facile Access to Benzofuran Derivatives through Radical Reactions with Heteroatom-centered Super-electron-donors. Research Square Platform LLC 2023. doi:10.21203/rs.3.rs-2405179/v1
  • Antoni, P. W.; Golz, C.; Hansmann, M. M. Organische Vier‐Elektronen Redox‐Systeme basierend auf Bipyridin‐ und Phenanthrolin‐Carben‐Architekturen. Angewandte Chemie 2022, 134. doi:10.1002/ange.202203064
  • Antoni, P. W.; Golz, C.; Hansmann, M. M. Organic Four-Electron Redox Systems Based on Bipyridine and Phenanthroline Carbene Architectures. Angewandte Chemie (International ed. in English) 2022, 61, e202203064. doi:10.1002/anie.202203064
  • McAteer, C.; Murugan, R.; Yamamoto, J. Pyridines and Their Benzo Derivatives: Applications. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 217–242. doi:10.1016/b978-0-12-818655-8.00065-2
  • Topal, S.; Isci, R.; Topal, S.; Karakaya, O.; Amna, B.; Gunturkun, D.; Ozturk, T. Comprehensive Heterocyclic Chemistry IV - 1,3-Dithioles. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 834–994. doi:10.1016/b978-0-12-818655-8.00138-4
  • Richard, N. A.; Charlton, G. D.; Dyker, C. A. Enhancing catalytic activity of pyridines via para-iminophosphorano substituents. Organic & biomolecular chemistry 2021, 19, 9167–9171. doi:10.1039/d1ob01630j
  • Zhao, Y.; Rollet, M.; Charles, L.; Canard, G.; Gigmes, D.; Vanelle, P.; Broggi, J. Switching from Single to Simultaneous Free-Radical and Anionic Polymerization with Enamine-Based Organic Electron Donors. Angewandte Chemie (International ed. in English) 2021, 60, 19389–19396. doi:10.1002/anie.202106733
  • Zhao, Y.; Rollet, M.; Charles, L.; Canard, G.; Gigmes, D.; Vanelle, P.; Broggi, J. Switching from Single to Simultaneous Free‐Radical and Anionic Polymerization with Enamine‐Based Organic Electron Donors. Angewandte Chemie 2021, 133, 19538–19545. doi:10.1002/ange.202106733
  • Alkhayri, F.; Dyker, C. A. Evaluation of Two-Electron Bispyridinylidene Anolytes and a TEMPO Catholyte for Non-Aqueous Redox Flow Batteries. Journal of The Electrochemical Society 2021, 168, 070501. doi:10.1149/1945-7111/ac0def
  • Frenette, B. L.; Arsenault, N.; Walker, S. L.; Decken, A.; Dyker, C. A. Bis(Iminophosphorano)-Substituted Pyridinium Ions and their Corresponding Bispyridinylidene Organic Electron Donors. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 8528–8536. doi:10.1002/chem.202100318
  • Meyer, A. G.; Bissember, A. C.; Hyland, C. J. T.; Williams, C. C.; Szabo, M.; Wales, S. M.; Constable, G. E. O.; Olivier, W. J. Seven-Membered Rings. Progress in Heterocyclic Chemistry 2021, 32, 565–614. doi:10.1016/b978-0-323-89812-6.00016-x
  • Alkhayri, F.; Dyker, C. A. A Two-Electron Bispyridinylidene Anolyte for Non-Aqueous Organic Redox Flow Batteries. Journal of The Electrochemical Society 2020, 167, 160548. doi:10.1149/1945-7111/abd492
  • Richard, N. A.; Khor, C. K.; Hetherington, S. M.; Mills, S. L.; Decken, A.; Dyker, C. A. Iminophosphorano-Substituted Bispyridinylidenes: Redox Potentials and Substituent Constants from Tolman Electronic Parameters. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 17371–17375. doi:10.1002/chem.202004153
  • Messelberger, J.; Grünwald, A.; Goodner, S. J.; Zeilinger, F.; Pinter, P.; Miehlich, M. E.; Heinemann, F. W.; Hansmann, M. M.; Munz, D. Aromaticity and Sterics Control Whether a Cationic Olefin Radical is Resistant to Disproportionation. Chemical science 2020, 11, 4138–4149. doi:10.1039/d0sc00699h
  • Yanagi, T.; Somerville, R. J.; Nogi, K.; Martin, R.; Yorimitsu, H. Ni-Catalyzed Carboxylation of C(sp2)–S Bonds with CO2: Evidence for the Multifaceted Role of Zn. ACS Catalysis 2020, 10, 2117–2123. doi:10.1021/acscatal.9b05141
  • Vaid, T. P.; Sanford, M. S. An organic super-electron-donor as a high energy density negative electrolyte for nonaqueous flow batteries. Chemical communications (Cambridge, England) 2019, 55, 11037–11040. doi:10.1039/c9cc06080d

Patents

  • DOROK SASCHA; STEUDTNER INA; HEGGEMANN ULRICH; RUNGE STEFFEN; KLOSE MANUELA. Electronic device and compound. US 10403824 B2, Sept 3, 2019.
  • DOROK SASCHA; STEUDTNER INA; HEGGEMANN ULRICH; RUNGE STEFFEN; MANUELA KLOSE. Electronic device and compound. CN 106575704 A, April 19, 2017.
  • DOROK SASCHA. ELECTRONIC DEVICE AND COMPOUND. WO 2016001425 A3, June 16, 2016.
  • DOROK SASCHA; STEUDTNER INA; HEGGEMANN ULRICH; RUNGE STEFFEN; KLOSE MANUELA. Electronic device and compound. EP 2963010 A1, Jan 6, 2016.
Other Beilstein-Institut Open Science Activities