1172-02-7Relevant articles and documents
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)
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.
Sulfoxide hemithioindigo tweezers - visible light addressable capture and release
Bartelmann, Thomas,Gnannt, Frederik,Zitzmann, Max,Mayer, Peter,Dube, Henry
, p. 3651 - 3659 (2021)
Introducing responsive elements into supramolecular recognition systems offers great advantages for the control of intermolecular interactions and represents an important stepping stone towards multi-purpose and reprogrammable synthetic systems. Of particular interest is implementation of light-responsiveness because of the unique ease and precision of this signal. Here we present visible light responsive hemithioindigo-based molecular tweezers that bear a highly polar sulfoxide function as an additional recognition unit inside their binding site. Sulfur oxidation allows to simultaneously enhance all crucial properties of this receptor typei.e.photoswitching capability, thermal stability of individual switching states, binding affinity, and binding modulation upon switching. With a novel titration method the thermodynamic binding parameters were determined using reduced sample amounts. Employing these strongly enhanced molecular tweezers allowed to demonstrate photocontrol of intermolecular charge transfer in a reversible manner.