<i>p</i>-Sulfonatocalix[6]arene-dodecyltrimethylammonium Supramolecular Amphiphilic System: Relationship between Calixarene and Micelle Concentration

Basílio, Nuno; Gómez, Borja; García‐Río, Luis

doi:10.1021/acs.langmuir.7b03084

Cited by 11 publications

(5 citation statements)

References 50 publications

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“…The construction of a stimuli-responsive nanosystem by the method of supramolecular assembly has attracted extensive attention benefitting from its simple composition, easy adjustment, and good repeatability. − In particular, the use of biocompatible water-soluble macrocyclic compounds, such as cyclodextrin, − p -sulfonatocalixarene, − cucurbituril, − and modified pillararene, − to construct stimuli-responsive supramolecular assemblies has shown many promising applications in the biomedical field. It is worth noting that organs, body fluids, and cell compartments have their unique pH values in living organisms.…”

Section: Introductionmentioning

confidence: 99%

pH-Triggered Transition from Micellar Aggregation to a Host–Guest Complex Accompanied by a Color Change

Wang

Gao

et al. 2022

Langmuir

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A pH-triggered transition from micellar aggregation to a host−guest complex was achieved based on the supramolecular interactions between calixpyridinium and pyrroloquinoline quinone disodium salt (PQQ-2Na) accompanied by a color change. Our design has the following three advantages: (1) a regular spherical micellar assembly is fabricated by the supramolecular interactions between calixpyridinium and PQQ-2Na at pH 6 in an aqueous solution, (2) increasing the pH can lead to a transition from micellar aggregation to a host−guest complex due to the deprotonation of calixpyridinium, and at the same time (3) increasing the pH can lead to a color change owing to the deprotonation of calixpyridinium and the complexation of deprotonated calixpyridinium with PQQ-2Na. Benefitting from the low toxicity of calixpyridinium and PQQ-2Na, this pH-induced transition from micellar aggregation to a host−guest complex was further studied as a controllable-release model.

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Section: Introductionmentioning

confidence: 99%

pH-Triggered Transition from Micellar Aggregation to a Host–Guest Complex Accompanied by a Color Change

Wang

Gao

et al. 2022

Langmuir

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“…The use for these purposes of supramolecular aggregates based on non-covalent host-guest complexes has a number of advantages, such as the simplicity of their preparation and modification with stimulussensitive and targeting ligands. A large number of works are devoted to the formation of mixed aggregates due to non-covalent interactions of macrocyclic hosts with open-chain surfactants and polymers [8][9][10][11]. Porphyrins are widely used as macrocycles in supramolecular aggregates due to their distinctive π-conjugated architecture, excellent photosensitivity, and biochemical functionality [12,13].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Self-Assembly of Porphyrin and Metallosurfactant as a Drug Nanocontainer Design

et al. 2022

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The combined method of treating malignant neoplasms using photodynamic therapy and chemotherapy is undoubtedly a promising and highly effective treatment method. The development and establishment of photodynamic cancer therapy is closely related to the creation of sensitizers based on porphyrins. The present study is devoted to the investigation of the spectroscopic, aggregation, and solubilization properties of the supramolecular system based on 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (TSPP) and lanthanum-containing surfactant (LaSurf) in an aqueous medium. The latter is a complex of lanthanum nitrate and two cationic amphiphilic molecules of 4-aza-1-hexadecylazoniabicyclo[2.2.2]octane bromide. The mixed TSPP–LaSurf complexes can spontaneously assemble into various nanostructures capable of binding the anticancer drug cisplatin. Morphological behavior, stability, and ability to drug binding of nanostructures can be tailored by varying the molar ratio and the concentration of components. The guest binding is shown to be additional factor controlling structural rearrangements and properties of the supramolecular TSPP–LaSurf complexes.

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“…Self-assembly processes are very important in the fields of biology, , chemistry, , and materials science. , The self-assembled morphology can be regulated by designing the building units precisely at the molecular level . Therefore, precisely controlling the self-assembled process and result is of great interest. , The host–guest recognition based on macrocycles has been widely applied in controlling the molecular self-assembly. , The first, second, and third generations of macrocycles, as well as the new generations of macrocycles, for instance, cucurbituril and pillararene, have been successfully employed as hosts in constructing well-defined self-assembled nanostructures. Recently, some new strategies were developed for supramolecular self-assembly based on macrocycles. − Even so, exploring a novel macrocycle-based controlled host–guest self-assembled system and further realizing its application, especially in aqueous solutions, is still a valuable and challenging research task.…”

Section: Introductionmentioning

confidence: 99%

“…8,9 The host−guest recognition based on macrocycles has been widely applied in controlling the molecular selfassembly. 10,11 The first, 12 second, 13 and third 14 generations of macrocycles, as well as the new generations of macrocycles, for instance, cucurbituril 15 and pillararene, 16 have been successfully employed as hosts in constructing well-defined selfassembled nanostructures. Recently, some new strategies were developed for supramolecular self-assembly based on macrocycles.…”

Section: ■ Introductionmentioning

confidence: 99%

Controlled Self-Assembly Mediated by the Complexation of Calixpyridinium: Diverse Assembled Morphology, Solid-State Fluorescence, and Iodine Capture Capacity

et al. 2021

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It is a great challenge to precisely control the molecules that self-assemble into diverse shapes with diverse properties. Herein, the self-assembled behaviors between calixpyridinium and two pyrenesulfonate guests, 1,3,6,8-pyrenetetrasulfonic acid tetrasodium salt (PyTS) and sodium 1-pyrenesulfonate (PS), were studied. The morphology and property of the two assemblies were quite different. PS guests self-assembled into spherical aggregates upon complexation with calixpyridinium, while the self-assembled rodlike aggregates were formed via the binding between calixpyridinium and PyTS guests. The calixpyridinium–PS supramolecular aggregates could not emit fluorescence in the solid state, while a strong green fluorescence was emitted by the calixpyridinium–PyTS supramolecular aggregates in the solid state. More interestingly and importantly, the solid calixpyridinium–PyTS supramolecular aggregates exhibited an adsorbent ability to iodine in both the aqueous solution and the vapor phase, while the solid calixpyridinium–PS supramolecular aggregates could not capture iodine. The diverse iodine capture capability of the two supramolecular aggregates was determined by the self-assembled structure at the molecular level.

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p-Sulfonatocalix[6]arene-dodecyltrimethylammonium Supramolecular Amphiphilic System: Relationship between Calixarene and Micelle Concentration

Cited by 11 publications

References 50 publications

pH-Triggered Transition from Micellar Aggregation to a Host–Guest Complex Accompanied by a Color Change

pH-Triggered Transition from Micellar Aggregation to a Host–Guest Complex Accompanied by a Color Change

Supramolecular Self-Assembly of Porphyrin and Metallosurfactant as a Drug Nanocontainer Design

Controlled Self-Assembly Mediated by the Complexation of Calixpyridinium: Diverse Assembled Morphology, Solid-State Fluorescence, and Iodine Capture Capacity

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