1241949-22-3Relevant academic research and scientific papers
Titanocene-Mediated Dinitrile Coupling: A Divergent Route to Nitrogen-Containing Polycyclic Aromatic Hydrocarbons
Kiel, Gavin R.,Samkian, Adrian E.,Nicolay, Amélie,Witzke, Ryan J.,Tilley, T. Don
, p. 2450 - 2454 (2018)
A general synthetic strategy for the construction of large, nitrogen-containing polycyclic aromatic hydrocarbons (PAHs) is reported. The strategy involves two key steps: (1) a titanocene-mediated reductive cyclization of an oligo(dinitrile) precursor to form a PAH appended with di(aza)titanacyclopentadiene functionality; (2) a divergent titanocene transfer reaction, which allows final-step installation of one or more o-quinone, diazole, or pyrazine units into the PAH framework. The new methodology enables rational, late-stage control of HOMO and LUMO energy levels and thus photophysical and electrochemical properties, as revealed by UV/vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. More generally, this contribution presents the first productive use of di(aza)metallacyclopentadiene intermediates in organic synthesis, including the first formal [2 + 2 + 2] reaction to form a pyrazine ring.
Extended 2,5-diazaphosphole oxides: Promising electron-acceptor building blocks for π-conjugated organic materials
Linder, Thomas,Sutherland, Todd C.,Baumgartner, Thomas
supporting information; experimental part, p. 7101 - 7105 (2010/09/14)
(Chemical equation presented) BTD makeover-phosphorus edition: Replacing the sulfur atom in πextended 2,1,3-benzo[c]thiadiazoles (BTD) by a phosphoryl group affords the materials with improved electronacceptor properties. The significantly lower reduction potentials and competitive electron-transfer rates make the new diazaphosphole oxides excellent candidates for application in π-conjugated organic materials (see figure).
