Constitutionally adaptive crown ether-based macrocyclic bolaamphiphile with redox-responsive switching of lower critical solution temperature behaviors

Xu, Qiangqiang; Cui, Zhiliyu; Yao, Jizhen; Li, Bo; Lv, Ping; Shen, Xin; Yu, Zehao; Gao, Yan; Qi, Zhenhui

doi:10.1016/j.cclet.2021.05.058

Cited by 8 publications

(6 citation statements)

References 49 publications

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“…Based on these results, the reversible transformation between the selenide-and selenoxide-containing CEs creates a switchable macrocycle pair (Figure 2A1) that differs dramatically in hydration and is controlled by redox stimuli. This constitutionally adaptive behavior of CEs offers an elegant platform for controlling and/or switching the hydration of bolaamphiphile skeletons (which are similar in structure to Argentinean boleadoras) (Xu et al, 2021). The resulting macrocyclic bolaamphiphile C7SeBola exhibited LCST behavior in water (Figure 2A2), and the overall LCST transition processes were highly reversible (Figure 2A3).…”

Section: Ces With Water: a Missing Type Of Watersoluble Macrocyclementioning

confidence: 95%

“…Both the crystal structure and theoretical modelling revealed that selenoxides are excellent hydrogen-bond (HB) acceptors, because the HB length of the selenoxide group (1.72 Å) is significantly shorter than that of the ether (-O-) group (1.90 Å). Qi et al found that the water solubility of C7SeOOH reaches 3,979 mM (Xu et al, 2021). By contrast, the water solubility of C7OH is 564 mM and that of C7SeOH is merely 74 mM.…”

Section: Ces With Water: a Missing Type Of Watersoluble Macrocyclementioning

confidence: 99%

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The aqueous supramolecular chemistry of crown ethers

Qin

Wang

et al. 2023

Front. Chem.

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This mini-review summarizes the seminal exploration of aqueous supramolecular chemistry of crown ether macrocycles. In history, most research of crown ethers were focusing on their supramolecular chemistry in organic phase or in gas phase. In sharp contrast, the recent research evidently reveal that crown ethers are very suitable for studying abroad range of the properties and applications of water interactions, from: high water-solubility, control of Hofmeister series, “structural water”, and supramolecular adhesives. Key studies revealing more details about the properties of water and aqueous solutions are highlighted.

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Section: Ces With Water: a Missing Type Of Watersoluble Macrocyclementioning

confidence: 95%

Section: Ces With Water: a Missing Type Of Watersoluble Macrocyclementioning

confidence: 99%

The aqueous supramolecular chemistry of crown ethers

Qin

Wang

et al. 2023

Front. Chem.

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“…Besides, controlling the LCST behaviour of crown ether-based small molecular systems is still challenging and rarely reported in response to external stimuli. 11,13…”

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confidence: 94%

pH-Responsive lower critical solution temperature behaviour of a dibenzo-24-crown-8 based low-molecular-weight gelator in water

et al. 2023

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“…These factors affect the microenvironment at the monolayer‐interface by stabilizing the carboxylate anion and/or making the carboxyl proton more acidic [17] . The sulfur is an electron‐rich atom [18] . The stronger interaction between the sulfur atom on the alpha carbon and the carboxylic acid group in the monolayer makes the carboxylate anion HSCH2COOH unstable.…”

Section: Introductionmentioning

confidence: 99%

Formation of Single‐Chain Anionic Bolaamphiphiles on Indium Tin Oxide Surfaces through Self‐Assembly To Improve Optoelectronic Device Performance

2023

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The surface of indium tin oxide (ITO) was modified with bolaamphiphilic (BA) materials to tune the energy-level alignment of electrodes in optoelectronic devices (OEDs). Tuning the energy-level alignment of the electrode is crucial for enhancing OED efficiency by improving carrier injection. Although the dielectric properties of organic solvents influence the formation of BA self-assembled monolayers (SAMs), our study found that the intermolecular forces of the dissolved BA materials and the solution medium are more important for the formation of a well-ordered film on the electrode. Our results also showed efficient tunneling phenomenon between the electrode and the hole transport layer (HTL) using BA material. The holes were transported to the tunnel junctions where the Fermi energy was sufficiently close to the HOMO band of the BA. Therefore, the tunnel barrier height of the ITO/HTL of the OED was reduced, and favorable conditions for hole injection was created, resulting in a 2-3 times increase in luminance and current density. It is believed that the larger area of interface contact between electrode/BA/HTL and the formation of wellordered BA layers are responsible for the improved performance of the BA-modified electrode surface and OED.

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Constitutionally adaptive crown ether-based macrocyclic bolaamphiphile with redox-responsive switching of lower critical solution temperature behaviors

Cited by 8 publications

References 49 publications

The aqueous supramolecular chemistry of crown ethers

The aqueous supramolecular chemistry of crown ethers

pH-Responsive lower critical solution temperature behaviour of a dibenzo-24-crown-8 based low-molecular-weight gelator in water

Formation of Single‐Chain Anionic Bolaamphiphiles on Indium Tin Oxide Surfaces through Self‐Assembly To Improve Optoelectronic Device Performance

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