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Beilstein J. Org. Chem. 2019, 15, 2408–2418, doi:10.3762/bjoc.15.233
Graphical Abstract
Scheme 1: The stiff stilbene photoisomerization from Z to E and vice versa by irradiation at 300 nm and 360 n...
Figure 1: The investigated SS-macrocycles (Z)-1a–d.
Scheme 2: Synthetic route to SS-macrocycles. i. (1) Triflic acid (3 equiv), DCM (dry), Ar atmosphere, MW (110...
Scheme 3: The photoisomerization of the stiff stilbene macrocycles, showing the stretching of the linker (gre...
Scheme 4: Noncyclic stiff stilbene diester 7 used as reference in the photoisomerization study.
Figure 2: The photoisomerization of the SS-macrocycles shows a clear correlation between the Z/E ratio in the...
Figure 3: Gibbs free energy differences (ΔG) between Z- and E-isomers of 1a–d and of the reference compound 7...
Figure 4: Ring strain for E and Z-isomers of 1a–d expressed as the Gibbs free energy difference to an acyclic...
Figure 5: The differences in ring strain between the E- and Z-isomers show an exponential correlation to the ...
Figure 6: Conformer ensembles for the macrocyclic stiff stilbene diethers 1a–d. Dihedral angles between the t...
Figure 7: Distances derived from NOE buildup experiments. Distances between pairs of protons or groups of pro...
Figure 8: Numbering of carbons in compounds 6a–d, showing 6d as an example.
Figure 9: Numbering of carbons in compounds (Z)-1a–d, showing (Z)-1d as an example.
Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265
Scheme 1: Previous and present EDOT functionalization routes.
Scheme 2: The synthetic route from glycidol to pyEDOT (3).
Scheme 3: The synthetic route from D-mannitol diketal to eEDOT 8 and TMS-eEDOT 8’.
Scheme 4: New EDOT derivatives 9–13 accessible from pyEDOT with bromo-pendant group precursors via Sonogashir...
Figure 1: CVs of electrochemical polymerization of (a) pyEDOT 3 and (b) EDOT in MeCN solution with 0.1 M TEAPF...
Figure 2: CVs of electrochemical polymerization of (a) pyEDOT-DeT (9), (b) pyEDOT-AQ (12) and (c) pyEDOT-MVPF...
Beilstein J. Org. Chem. 2016, 12, 89–96, doi:10.3762/bjoc.12.10
Figure 1: Structure of pyrrole/hydroquinone derivatives 3-(2,5-dimethoxyphenyl)-1H-pyrrole (1) and 3-(1,4-dih...
Figure 2: Hydroquinone dimethyl ether functionalized pyrroles with linkers L discussed in this study.
Scheme 1: Synthetic route for 3-(2,5-dimethoxybenzyl)-1H-pyrrole (3a). Conditions: i) Pd(PPh3)4, Na2CO3 (2 M ...
Scheme 2: Synthetic route for 3-(2,5-dimethoxystyryl)-1H-pyrrole (3c); cis-4c and trans-4c were separated chr...
Scheme 3: Synthesis of 3-((2,5-dimethoxyphenyl)ethynyl)-1H-pyrrole (3d). Conditions: i) Ethynyltrimethylsilan...
Scheme 4: Synthesis of 3-(2,5-dimethoxyphenethyl)-1H-pyrrole (3b). Conditions: i) Pd/C, MeOH/acetone, rt, 1.5...
Figure 3: 1H NMR spectra (400 MHz, CDCl3 solution) of the DMB-pyrrole dyads (aliphatic signals not shown).
Figure 4: 13C NMR spectra (100.6 MHz, CDCl3 solution) of the DMB-pyrrole dyads (aliphatic signals not shown).
Figure 5: UV–vis absorption spectra of 1, 3a–d, (full lines) and the reference compounds DMB, DMB-VI, DMB-EN ...
Figure 6: Calculated HOMO for 3a (a) and 3d (b).