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1 article(s) from Szyszko, Bartosz

Tying a knot between crown ethers and porphyrins

Maksym Matviyishyn and
Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

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Graphical Abstract

Figure 1: Porphyrin and crown ether.

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Figure 2: Timeline demonstrating the contributions into the crown ether–porphyrin chemistry.

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Figure 3: Tetra-crowned porphyrin 1 and dimer 2 formed upon K⁺ binding.

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Figure 4: meso-Crowned 25-oxasmaragdyrins 3a–c and their boron(III) complexes (3a–c)-BF₂.

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Scheme 1: CsF ion-pair binding of 4. The molecular structure of 4-CsF is shown on the right [101].

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Figure 5: CsF ion pair binding by 5. The molecular structure of 5-CsF is shown on the right [102].

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Scheme 2: Ion-pair binding by 6. The molecular structure of (6-CsCl)₂ is shown on the right [103].

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Scheme 3: Hydrated fluoride binding by 7 [104].

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Figure 6: β-Crowned porphyrin 8.

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Figure 7: Crown ether-capped porphyrins 9.

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Figure 8: The capped porphyrin 10 and complex [10-PQ](PF₆)₂.

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Figure 9: The double-capped porphyrin 11.

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Figure 10: Selected examples of iminoporphyrinoids [58,122].

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Scheme 4: The synthesis of 13.

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Scheme 5: Tripyrrane-based crown ether-embedding porphyrinoid 15.

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Figure 11: Macrocycles 16–19 and their coordination compounds.

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Scheme 6: The flexibility of 16-Co [66].

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Figure 12: Hexagonal wheel composed of six 16-Co(III) monomers [66].

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Scheme 7: The synthesis of 16-V [67].

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Figure 13: The molecular structure of dimers [16-Mn]₂ [67].

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Scheme 8: Synthesis of crownphyrins 28–33. Compounds 23a/b and 29a/b were obtained from 4,7,10-trioxa-1,13-tr...

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Figure 14: The molecular structures of 22a, 34a·(HCl)₂, and 29b [69].

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Figure 15: Molecular structures of 22a-Pb and (29b)₂-Zn [69].

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Scheme 9: Reactivity of 29a/b.

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Scheme 10: Synthesis of 36 and 37 [131].

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Scheme 11: Synthesis of 40–45.

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Figure 16: Potential applications of porphyrin-crown ether hybrids.

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Perspective

Published 27 Oct 2023

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