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Search for "photo-switch" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

is derived from the hydrophobic-interaction-based inclusion formation; thus they are only low number of reports on their structural control. The photoisomerization-based structural control system is often applied to CD-based rotaxane. Typically, the photo-switch behavior is used, and it is based on

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Graphical Abstract

Figure 1: Overview of the CD-based rotaxane as a polymer material covered in this review.

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Figure 2: CD structure.

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Figure 3: Typical pathway for synthesizing CD-based rotaxanes.

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Scheme 1: (A) Synthesis of α-CD-based [2]rotaxane via a metal–ligand complex. (B) Chemical structures of meth...

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Scheme 2: Synthesis of α-CD-based polyrotaxane.

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Scheme 3: Facile [3]rotaxane synthesis by the urea end-capping method.

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Figure 4: (A) Single-crystal structure of α-CD-based [3]rotaxane 3 and PMα-CD-based [3]rotaxane 4. (B) Schema...

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Figure 5: Structural control of CD-based [2]rotaxane via (A) light irradiation and (B) light irradiation and ...

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Figure 6: Relationship among the plus–minus signs of ICD, the position of the guest molecule, and the axis of...

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Figure 7: Structural control of CD-based rotaxane via (A) redox reaction and (B) in a solvent.

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Scheme 4: (A) Synthesis of pseudopolyrotaxane bearing an ABA triblock copolymer as an axle. (B) Two synthetic...

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Scheme 5: Slippage of size-complementary rotaxanes.

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Figure 8: (A) Reversible formation of the CD-based [2]rotaxane. (B) Deslipping reaction of the CD-based size-...

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Figure 9: (A) Chemical structures of [3]rotaxanes 2 and 3. (B) Schematic of the deslipping reaction of [3]rot...

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Figure 10: (A) Modification of the axle ends of [3]rotaxane by (1) bromination and (2) the Suzuki coupling rea...

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Figure 11: (A) ICD spectra of [3]rotaxanes bearing acylated (top) and conventional (bottom) CDs. (B) Schematic...

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Figure 12: Synthesis of macromolecular[3]rotaxane via a size-complementary protocol.

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Figure 13: Conjugated polymer insulated by (A) β-CD. (B) Triphenylamine-substituted β-CD.

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Figure 14: Synthesis of the VSC and successive rotaxane-crosslinked polymer (RCP) preparation.

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Figure 15: (A) Chemical structure of the [3]rotaxane crosslinker (RC). (B) Schematic of the synthesis and de-c...

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Figure 16: (A) Random vinylation of the CD-based [3]rotaxane; (B) Schematic of the reaction between α-CD and m...

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Figure 17: (A) Aggregation of CD-based [3]rotaxane. (B) Schematic of the plausible mechanism of the aggregatio...

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Review

Published 19 Nov 2024

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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

the resulting macrocycle. Keywords: DFT; molecular mechanics; photostability; photo-switch; ring-strain; stiff stilbene; Introduction The stiff stilbene (SS) molecule has drawn a lot of interest due to its photodynamic properties [1]. Stiff stilbenes typically undergo light triggered isomerization

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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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Full Research Paper

Published 11 Oct 2019

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