Efficient electrocatalytic H2O2 evolution utilizing electron-conducting molecular wires spatially separated by rotaxane encapsulation

Chou, Sheng-Ying; Masai, Hiroshi; Otani, Masaya; Miyagishi, Hiromichi V.; Sakamoto, Gentaro; Yamada, Yusuke; Kinoshita, Yusuke; Tamiaki, Hitoshi; Katase, Takayoshi; Ohta, Hiromichi; Kondo, Tomoki; Nakada, Akinobu; Abe, Ryu; Tanaka, Takahisa; Uchida, Ken; Terao, Jun

doi:10.1016/j.apcatb.2023.122373

Cited by 6 publications

(2 citation statements)

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“…Researchers have improved charge transport, [31][32][33] electrochromic behavior, [34][35][36] and electrocatalytic activity by integrating redox-active molecules or metal complexes into supramolecular structures. [37][38][39][40] The creation of next-generation electrical and energy conversion devices is possible with the help of these electroactive supramolecular structures. Advanced electrode materials for energy storage devices like batteries and supercapacitors have been created using supramolecular chemistry to improve the electrode materials' stability and electrochemical performance.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical switching in mechanically interlocked molecules (MIMs)

Bhadani,

Kathiresan

2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Electrochemical switching in mechanically interlocked molecules (MIMs)

Bhadani,

Kathiresan

2024

Org. Chem. Front.

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“…Our group has developed numerous linked rotaxanes using permethylated α-cyclodextrin (PM α-CD) and diphenylacetylene (DPA). [39][40][41][42][43][44][45][46][47] The linked rotaxane can be switched between the inclusion and uninclusion structures by adjusting the solvent polarity. 40,[48][49][50][51] The threading/dethreading processes occur via two pathways: the head and tail pathways.…”

Section: Introductionmentioning

confidence: 99%

Bidirectional Molecular Motors by Controlling Threading and Dethreading Pathways of a Linked Rotaxane

Miyagishi,

Masai,

Terao

2023

Preprint

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Artificial molecular motors have attracted significant attention as models of biological machines and molecular motors. Unlike conventional artificial molecular motors, which rely on covalent bond rotation, molecular motors with mechanically interlocked molecules (MIM) generate significant rotational motion via the dynamic shuttling of the macrocyclic components and have thus attracted considerable attention. The topology of MIM-type molecular motors is currently limited to catenane structures, which require intricate synthetic procedures that typically produce a low synthetic yield. In this study, we develop a novel class of MIM-type molecular motors based on a rotaxane-type topology. The switching of the rotaxane threading/dethreading pathway of the linked rotaxane by protection/deprotection of the bulky stopper group and changes in solvent polarity enabled unidirectional rotation of the molecular motor. Detailed spectroscopic investigations provide a quantitative evaluation of the threading/dethreading reaction rates. Repeated unidirectional rotation and switching of the direction of rotation is achieved by controlling the reaction rates. Our findings demonstrate that linked rotaxanes can serve as MIM-type molecular motors whose rotation direction can be switched by controlling the threading/dethreading reactions; these motors are expected to find applications as a component of molecular machinery.

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Insulated π‐Conjugated Azido Scaffolds for Stepwise Functionalization via Huisgen Cycloaddition on Metal Oxide Surfaces

Jiang,

Iwai,

et al. 2024

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In organic−inorganic hybrid devices, fine interfacial controls by organic components directly affect the device performance. However, fabrication of uniformed interfaces using π‐conjugated molecules remains challenging due to facile aggregation by their strong π‐π interaction. In this report, a π‐conjugated scaffold insulated by covalently linked permethylated α‐cyclodextrin moiety with an azido group is synthesized for surface Huisgen cycloaddition on metal oxides. Fourier‐transformed infrared (FT‐IR) spectroscopy and X‐ray photoelectron spectroscopy confirm the successful immobilization of the insulated azido scaffold on ZnO nanowire array surfaces. Owing to the highly independent immobilization, the scaffold allows rapid and complete conversion of the surface azido group in Huisgen cycloaddition reactions with ethynyl‐terminated molecules, as confirmed by FT‐IR spectroscopy monitoring. Cyclic voltammetry analysis of modified indium tin oxide substrates shows the positive effects of cyclic insulation toward suppression of intermolecular interaction between molecules introduced by the surface Huisgen cycloaddition reactions. The utility of the scaffold for heterogeneous catalysis is demonstrated in electrocatalytic selective O2 reduction to H2O2 with cobalt(II) chlorin modified fluorine doped tin oxide electrode and photocatalytic H2 generation with iridium(III) dye‐sensitized Pt‐loaded TiO2 nanoparticle. These results highlight the potential of the insulated azido scaffold for a stepwise functionalization process, enabling precise and well‐defined hybrid interfaces.

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Efficient electrocatalytic H2O2 evolution utilizing electron-conducting molecular wires spatially separated by rotaxane encapsulation

Cited by 6 publications

References 46 publications

Electrochemical switching in mechanically interlocked molecules (MIMs)

Electrochemical switching in mechanically interlocked molecules (MIMs)

Bidirectional Molecular Motors by Controlling Threading and Dethreading Pathways of a Linked Rotaxane

Insulated π‐Conjugated Azido Scaffolds for Stepwise Functionalization via Huisgen Cycloaddition on Metal Oxide Surfaces

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