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1 article(s) from Olsson, Sandra

Effect of ring size on photoisomerization properties of stiff stilbene macrocycles

Sandra Olsson,
Óscar Benito Pérez,
Magnus Blom and
Adolf Gogoll

Beilstein J. Org. Chem. 2019, 15, 2408–2418, doi:10.3762/bjoc.15.233

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Graphical Abstract

Scheme 1: The stiff stilbene photoisomerization from Z to E and vice versa by irradiation at 300 nm and 360 n...

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Figure 1: The investigated SS-macrocycles (Z)-1a–d.

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Scheme 2: Synthetic route to SS-macrocycles. i. (1) Triflic acid (3 equiv), DCM (dry), Ar atmosphere, MW (110...

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Scheme 3: The photoisomerization of the stiff stilbene macrocycles, showing the stretching of the linker (gre...

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Scheme 4: Noncyclic stiff stilbene diester 7 used as reference in the photoisomerization study.

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Figure 2: The photoisomerization of the SS-macrocycles shows a clear correlation between the Z/E ratio in the...

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Figure 3: Gibbs free energy differences (ΔG) between Z- and E-isomers of 1a–d and of the reference compound 7...

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Figure 4: Ring strain for E and Z-isomers of 1a–d expressed as the Gibbs free energy difference to an acyclic...

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Figure 5: The differences in ring strain between the E- and Z-isomers show an exponential correlation to the ...

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Figure 6: Conformer ensembles for the macrocyclic stiff stilbene diethers 1a–d. Dihedral angles between the t...

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Figure 7: Distances derived from NOE buildup experiments. Distances between pairs of protons or groups of pro...

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Figure 8: Numbering of carbons in compounds 6a–d, showing 6d as an example.

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Figure 9: Numbering of carbons in compounds (Z)-1a–d, showing (Z)-1d as an example.

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Published 11 Oct 2019

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