A Fluorescence Study on Guest Release of Reduction-responsive Host-guest Conjugates Having a Disulfide Bond

Hayashida, Osamu; Imamura, S.; Miyazaki, Takaaki

doi:10.1246/cl.220259

Cited by 4 publications

(1 citation statement)

References 18 publications

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“…Hence, in addition to 1a and 1b , especially nonionic 1c tends to form self-aggregates in H 2 O-rich solvent mixtures because there is no electrostatic repulsion for 1c . On the other hand, there are no meaningful differences between 1a , 1b , and 1c in a (CH 3 ) 2 SO-rich solvent mixture (80%), and these results show that 1a , 1b , and 1c exist in a monomeric form. − …”

Section: Resultsmentioning

confidence: 79%

Self-Aggregation, Enhanced Guest-Binding Behavior, and Anion-Induced Agglutination of Cyclophane Dimers Linked with Florescent Perylene Diimide

Hayashida,

Araki,

Miyazaki

2024

J. Org. Chem.

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Cationic, anionic, and nonionic cyclophane dimers, 1a, 1b, and 1c, covalently linked with fluorescent perylene diimide were synthesized, respectively, as a host for aggregation-induced multivalent effects on guest-binding. These PDI-linked cyclophane dimers 1a and 1b, especially 1c, formed self-aggregates in H 2 O-rich solvents through π-stacking interactions. Critical aggregation concentrations of 1a, 1b, and 1c in H 2 O were 4.0 × 10 −6 , 4.0 × 10 −6 , and less than 0.1 × 10 −6 M, respectively. The selfaggregates of the PDI-linked cyclophane dimers in H 2 O were several hundred nanometers in size by DLS and TEM measurements. In an aggregated state, 1a exhibited guest-binding abilities toward hydrophobic guests, such as 6-p-toluidinonaphthalene-2-sulfonate and 6-anilino-naphthalene-2-sulfonate. Moreover, anion-induced agglutination of 1a was observed upon the addition of phosphate ions, and its effectiveness was as follows: ATP > ADP > H 2 P 2 O 7 2− > AMP ≈ PO 4 3− > HPO 4 2− > H 2 PO 4 − . The contribution of the adenine base of the nucleotides as a guest moiety used for effective agglutination was confirmed by 1 H NMR spectroscopy.

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Section: Resultsmentioning

confidence: 79%

Self-Aggregation, Enhanced Guest-Binding Behavior, and Anion-Induced Agglutination of Cyclophane Dimers Linked with Florescent Perylene Diimide

Hayashida,

Araki,

Miyazaki

2024

J. Org. Chem.

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Ratiometric Fluorescence Depending on In/Out Isomerism of Host‐Guest Conjugate Having a Fluorosolvatochromic Dye

Tsutsumi,

Miyazaki,

Fujita

et al. 2024

Eur J Org Chem

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Host‐guest conjugate is a promising strategy for providing outstanding molecules. Herein, we designed host‐guest conjugate HG1, which comprises a hydrophilic host unit, tetraaza[2.2.1.2.2.1]paracyclophane CPX2with a microhydrophobic cavity, and a guest unit, 2,3‐naphthalimide fused with two benzothiophenes G1 exhibiting fluorosolvatochromism, linked with an oxyethylene chain. HG1 initially showed a fluorescence band at 585 nm in MeOH/H2O (1/499 v/v); however, this band decreased with time, and instead, a new band at 430 nm appeared. The CIE chromaticity diagram showed that the fluorescent color changed from yellow‐orange to blue via white. NMR analysis of HG1 in methanol‐d4 exhibited different signals of the G1 unit between the blue and yellow fluorescent structures. The blue fluorescent structures showed asymmetrical signals assigned as the G1 unit, affected by the cavity environment of the CPX2 unit. Consequently, HG1 can form two conformations: In‐form and Out‐form. In In‐form, the G1 unit is inside the hydrophobic cavity of the CPX2 unit and shows blue fluorescence. In Out‐form, the G1 unit is outside the CPX2 unit and shows yellow fluorescence in an aqueous solvent. Therefore, HG1 performs as a ratiometric fluorophore depending on the in/out isomerism of the host‐guest conjugate.

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Fluorescent and colorimetric sensors for anions: Highlights from 2020 to 2022

Picci,

Montis,

Gilchrist

et al. 2024

Coordination Chemistry Reviews

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A Fluorescence Study on Guest Release of Reduction-responsive Host-guest Conjugates Having a Disulfide Bond

Cited by 4 publications

References 18 publications

Self-Aggregation, Enhanced Guest-Binding Behavior, and Anion-Induced Agglutination of Cyclophane Dimers Linked with Florescent Perylene Diimide

Self-Aggregation, Enhanced Guest-Binding Behavior, and Anion-Induced Agglutination of Cyclophane Dimers Linked with Florescent Perylene Diimide

Ratiometric Fluorescence Depending on In/Out Isomerism of Host‐Guest Conjugate Having a Fluorosolvatochromic Dye

Fluorescent and colorimetric sensors for anions: Highlights from 2020 to 2022

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