15517-55-2Relevant articles and documents
Electron Acceptors of the Fluorene Series. 7.1 2,7-Dicyano-4,5-dinitro-9-X-fluorenes: Synthesis, Cyclic Voltammetry, Charge Transfer Complexation with N-Propylcarbazole in Solution, and X-ray Crystal Structures of Two Tetrathiafulvalene Complexes
Perepichka, Igor F.,Kuz'mina, Lyudmila G.,Perepichka, Dmitrii F.,Bryce, Martin R.,Goldenberg, Leonid M.,Popov, Anatolii F.,Howard, Judith A. K.
, p. 6484 - 6493 (1998)
The synthesis and physical properties of a series of novel fluorene π-electron acceptors (7-9) are described. Cyclic voltammograms of 7 and 8 exhibit three separate reversible (or quasi-reversible) one-electron redox waves, characteristic of strong electron acceptors. Spectroelectrochemical experiments show the appearance in the long-wavelength visible region of absorption bands at appropriate potentials which were attributed to the transformations A → A.- and A.- → A2-. Charge-transfer complexation with N-propylcarbazole in dioxane shows the formation of 1:1 complexes with parameters characteristic for other fluorene acceptors. The single-crystal X-ray structures of 1:1 charge-transfer complexes of tetrathiafulvalene with the electron acceptor 8 and with the strongest fluorene acceptor If both show ...A...D...A...D... stacking in the crystal.
Crystal growth and characterization of solvated organic charge-transfer complexes built on TTF and 9-dicyanomethylenefluorene derivatives
Salmern-Valverde, Amparo,Berns, Sylvain
, p. 6227 - 6235 (2015/08/11)
A series of 1 : 1 organic complexes have been synthesized by reaction between TTF (tetrathiafulvalene) and three 9-dicyanomethylenefluorene derivatives: 9-dicyanomethylene-2,7-dinitrofluorene (DDF), 9-dicyanomethylene-2,4,7-trinitrofluorene (DTF) and 9-dicyanomethylene-4,5,7-trinitrofluorene-2-carboxylic acid (DC2TF). The following formulas were determined by X-ray diffraction and elemental analysis for these complexes: (TTF-DDF)·CH3CN (1), (TTF-DDF)·0.5PhCl (2), (TTF-DTF)·CH3CN (3), (TTF-DTF)·0.5Me2CO (4) and (TTF-DC2TF)·H2O (5). A sixth solvated compound was also obtained, with a different stoichiometry, (TTF)3(DC2TF)2·2CH3CN (6). The degree of charge transfer in 1-5 was estimated by IR and Raman spectroscopy. The lattice solvent, acetonitrile, chlorobenzene, or acetone is slowly released from the crystals of complexes 1-4, inducing a significant decrease in charge transfer over time. These crystals converge over months towards materials close to the neutral state. Hydrate 5 is air-stable, and displays a degree of charge transfer, δ = 0.48 e-, close to the range of semiconducting or metal-organic complexes. Finally, compound 6 is an ionic crystal, and is thus expected to be an insulating material.
Engineering a remarkably low HOMO-LUMO gap by covalent linkage of a strong π-donor and a π-acceptor - Tetrathiafulvalene-σ-polynitrofluorene diads: Their amphoteric redox behavior, electron transfer and spectroscopic properties
Perepichka, Dmitrii F.,Bryce, Martin R.,Batsanov, Andrei S.,McInnes, Eric J. L.,Zhao, Jing P.,Farley, Robert D.
, p. 4656 - 4669 (2007/10/03)
Novel R3TTF-σ-A compounds 14, 16 and 19 (R3TTF=trial-kyltetrathiafulvalene, σ = saturated spacer, A = polynitrofluoren-9-dicyanomethylene acceptor) incorporating very strong donor and acceptor moieties have been synthesized by conden
