Phototransduction in a supramolecular cascade: a mimic for essential features of the vision process

Wu, Jialei Chen; Máximo, Patrícia; Remón, Patricia; Parola, A. Jorge; Basílio, Nuno; Pischel, Uwe

doi:10.1039/d3cc00384a

“…3B ). The binding affinity of phenylephrine to CB7 is found to be higher than that of dopamine 40 (a structurally similar catecholamine), which might be attributed to the position of a hydroxyl group at the side chain of phenylephrine rather than at the phenyl ring in dopamine.…”

Section: Resultsmentioning

confidence: 91%

Supramolecular complexation of phenylephrine by cucurbit[7]uril in aqueous solution

Assaf,

Faraj,

Abu-Nameh

et al. 2024

RSC Adv.

1

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A Photoswitchable Macrocycle Controls Anion‐Templated Pseudorotaxane Formation and Axle Relocalization

de Jong,

Siegler,

Wezenberg

2023

Angewandte Chemie

0

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Important biological processes, such as signaling and transport, are regulated by dynamic binding events. The development of artificial supramolecular systems in which binding between different components is controlled could help emulate such processes. Herein, we describe stiff‐stilbene‐containing macrocycles that can be switched between (Z)‐ and (E)‐isomers by light, as demonstrated by UV/Vis and 1H NMR spectroscopy. The (Z)‐isomers can be effectively threaded by pyridinium halide axles to give pseudorotaxane complexes, as confirmed by 1H NMR titration studies and single‐crystal X‐ray crystallography. The overall stability of these complexes can be tuned by varying the templating counteranion. However, upon light‐induced isomerization to the (E)‐isomer, the threading capability is drastically reduced. The axle component, in addition, can form a heterodimeric complex with a secondary isophthalamide host. Therefore, when all components are combined, light irradiation triggers axle exchange between the macrocycle and this secondary host, which has been monitored by 1H NMR spectroscopy and simulated computationally.

show abstract

A Photoswitchable Macrocycle Controls Anion‐Templated Pseudorotaxane Formation and Axle Relocalization

de Jong,

Siegler,

Wezenberg

2023

Angew Chem Int Ed

2

0

View full text Add to dashboard Cite

Important biological processes, such as signaling and transport, are regulated by dynamic binding events. The development of artificial supramolecular systems in which binding between different components is controlled could help emulate such processes. Herein, we describe stiff‐stilbene‐containing macrocycles that can be switched between (Z)‐ and (E)‐isomers by light, as demonstrated by UV/Vis and 1H NMR spectroscopy. The (Z)‐isomers can be effectively threaded by pyridinium halide axles to give pseudorotaxane complexes, as confirmed by 1H NMR titration studies and single‐crystal X‐ray crystallography. The overall stability of these complexes can be tuned by varying the templating counteranion. However, upon light‐induced isomerization to the (E)‐isomer, the threading capability is drastically reduced. The axle component, in addition, can form a heterodimeric complex with a secondary isophthalamide host. Therefore, when all components are combined, light irradiation triggers axle exchange between the macrocycle and this secondary host, which has been monitored by 1H NMR spectroscopy and simulated computationally.

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Phototransduction in a supramolecular cascade: a mimic for essential features of the vision process

Abstract: The tailored design of a light-triggered supramolecular cascade results in an artifical machinery that assimilates the transduction of photons into chemical communication and the final release of a neurotransmitter. This...

Cited by 3 publications

References 58 publications

Supramolecular complexation of phenylephrine by cucurbit[7]uril in aqueous solution

Supramolecular complexation of phenylephrine by cucurbit[7]uril in aqueous solution

A Photoswitchable Macrocycle Controls Anion‐Templated Pseudorotaxane Formation and Axle Relocalization

A Photoswitchable Macrocycle Controls Anion‐Templated Pseudorotaxane Formation and Axle Relocalization

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