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Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149
Graphical Abstract
Scheme 1: Multifunctional TTF-appended azine ligands.
Scheme 2: Synthetic scheme for TTF-based azine ligands L1 and L2.
Figure 1: Crystal structure of ligand L1 with atom numbering scheme (top) and a side view of the molecule (bo...
Figure 2: Partial crystal packing of ligand L1 with formation of head to tail dimers that stack along a-axis ...
Figure 3: Packing diagram of L1 showing the orientation of the columns of head to tail dimers.
Figure 4: UV–visible absorption spectra of ligands L1 and L2 (c 2.5 × 10−5 M in (dichloromethane/acetonitrile...
Figure 5: HOMO–LUMO Frontier orbitals representation for ligands L1 and L2.
Figure 6: Cyclic voltammograms of ligands L1 and L2 (2 × 10−5 M) in CH2Cl2/CH3CN (9:1, v/v) at 100 mV·s−1 on ...
Figure 7: UV–visible spectral changes of ligand L2 (2 × 10−5 M in CH2Cl2/CH3CN, 9/1) upon addition of TBAF.
Figure 8: 1H NMR spectra of ligand L2 (4·10−3 M in DMSO-d6) upon addition of successive aliquots of TBAF (DMS...
Figure 9: Crystal structure of complex 3 with atom numbering scheme (top) and a side view of the molecule (bo...
Figure 10: Pattern of intramolecular and intermolecular contacts in 3. Two molecules are linked by pairs of st...
Figure 11: Layered structure of complex 3 viewed along the a-axis. The dimers are linked together through hydr...
Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115
Figure 1: Structures of molecular clips 1–4.
Scheme 1: Different routes developed for the synthesis of molecular clips 1–4.
Scheme 2: Reaction between diphenylglycoluril with 4,5-bis(bromomethyl)-2-thioxo-1,3-dithiole.
Figure 2: Intramolecular distances between TTF moieties from X-ray analysis for clips 2 and 3 and theoretical...
Figure 3: Cyclic voltammograms of molecular clips 1, 2, 3, 4 and F4-TCNQ at 10−3 M in 0.1 M TBAPF6/CH2Cl2/CH3...
Figure 4: Cyclic voltammograms of molecular clip 2 at different concentrations (left: 10−5 M; middle: 10−4 M;...
Scheme 3: Graphical representation of the stepwise oxidation of molecular clips 1, 2 and 3.
Scheme 4: Electrochemical mechanism used to simulate the CVs of molecular clips 1, 2 and 3.
Figure 5: Chemical oxidation of molecular clip 1 (10−4 M, CH2Cl2) using aliquots of NOSbF6 oxidizing reagent ...
Figure 6: Spectroelectrochemical experiment of molecular clip 1 during the first oxidation step at different ...
Figure 7: Molecular structure of molecular clip 15 and representation of its stepwise oxidation processes pro...
Figure 8: Molecular packing diagram of clips 2 (left) and 3 (right) obtained from X-ray analysis. A molecule ...
Figure 9: Left: Job plot analysis for DNB vs molecular clip 3 ([3 + DNB] = 10−3 M in o-C6H4Cl2 at 800 nm) at ...
Figure 10: UV–visible absorption spectra of F4-TCNQ (CH2Cl2, 10−5 M) upon titration with molecular clip 3 (CH2...
Figure 11: Redox interaction (left) and complexation (right) of F4-TCNQ with molecular clips 3 and 4.