321895-46-9Relevant academic research and scientific papers
First binuclear complex of an N,N',N'',N'''-tetraalkyl 2,5-diamino-1,4-benzoquinonediimine
Siri,Braunstein
, p. 2223 - 2224 (2000)
A new method for the synthesis of N,N',N'',N'''-tetraalkyl 2,5-diamino-1,4-benzoquinonediimines is described together with the structure of a binuclear Pt(II) complex with such a bridging ligand which provides an extended π-system.
One-electron oxidation-induced dimerising C-C coupling of a 2,5-diamino-1,4-benzoquinonediimine: A chemical and electrochemical investigation
Taquet, Jean-Philippe,Siri, Olivier,Collin, Jean-Paul,Messaoudi, Abdellatif,Braunstein, Pierre
, p. 188 - 192 (2005)
The one-electron oxidation of N,N′,N″,N?-tetraneopentyl- 2,5-diamino-1,4-benzoquinonediimine 3 has been carried out using Ag(I) as an oxidising agent and led to the formation of the postulated nitrogen-based radical cation B. This unstable species can evolve by following two competing pathways, either a hydrogen atom abstraction from a THF solvent molecule, which leads to the N,N′,N″,N?-tetraneopentyl-2,5-diamino-1,4- benzoquinonemonoiminemonoiminium triflate 5, or a dimerisation of two carbon-based radical cations C, which affords the new dimer 4. An X-ray diffraction study of the latter established the presence of a centre of symmetry in the middle of the newly formed Csp3-Csp3 bond. Breaking of this bond upon reduction regenerates 3 under mild conditions. This type of chemically induced formation/breaking of a C-C single bond appears to be unprecedented in quinonoid chemistry. Electrochemical studies performed in THF confirm the proposed mechanism for the one-electron oxidation process.
Novel "Potentially Antiaromatic", Acidichromic Quinonediimines with Tunable Delocalization of Their 6π-Electron Subunits
Siri, Olivier,Braunstein, Pierre,Rohmer, Marie-Madeleine,Benard, Marc,Welter, Richard
, p. 13793 - 13803 (2007/10/03)
We present a novel family of "potentially antiaromatic" alkyl-substituted p-benzoquinonediimine pH-dependent chromophores. It appears from the structural data that these overall 12π-electron molecules should be better considered as constituted by two chem
