Selective Metal-Ion-Mediated Vesicle Adhesion Based on Dynamic Self-Organization of a Pyrene-Appended Glutamic Acid

Xing, Peng; Wang, Yajie; Yang, Minmin; Zhang, Yimeng; Wang, Bo; Hao, Aiyou

doi:10.1021/acsami.6b04279

Cited by 16 publications

(9 citation statements)

References 47 publications

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“…Self‐aggregation of PDG and NDG was investigated in nonpolar solvent (decane) and polar solvent (water). Concentrated stock solutions of building units in decane‐ or water‐miscible solvents like THF were mixed with decane or water to give aggregation systems with desirable concentrations through the solvent exchange protocol . The observation of macroscopic phase behavior indicates that the aggregation occurs even at a low concentration of 0.1 × 10 −3 m , displaying the precipitate (NDG) or flocculent/half‐gel (PDG) production.…”

Section: Resultsmentioning

confidence: 99%

Solvent‐Controlled Assembly of Aromatic Glutamic Dendrimers for Efficient Luminescent Color Conversion

Xing

Yang

Wang

et al. 2018

Adv Funct Materials

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A binary supramolecular system where self-sorting and coassembly behavior can be switched by changing the solvent polarity is hereby reported. Glutamic dendron is separately conjugated with pyrene and naphthalimide luminophores through an alkyl spacer. The resulting structurally similar building units can self-assemble into one-dimensional micro/nanostructures with hexagonal and lamellar packing, respectively. Varying solvents from polar aqueous solution to nonpolar decane is evidenced to profoundly inverse the superchirality and switch self-sorted assembly to coassembly of the two building blocks. The moisture sensitivity of the naphthalimide moiety is considered the primary driving force for the self-sorting phenomenon in aqueous solution, resulting in inevitable hydration to repel its stacking with hydrophobic pyrene moiety. On the other hand, the naphthalimide unit can integrate segmentally with the pyrene unit in decane, greatly facilitating the nanofiber growth and supramolecular gel formation along with improved energy transfer efficiency between luminophores. As a result, the coassembly-based thin films show efficient luminescent color conversion upon the UV light irradiation. This research presents a useful route for the fabrication of controllable solution-processed light emitting devices from self-assembled multicomponent systems.

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Section: Resultsmentioning

confidence: 99%

Solvent‐Controlled Assembly of Aromatic Glutamic Dendrimers for Efficient Luminescent Color Conversion

Xing

Yang

Wang

et al. 2018

Adv Funct Materials

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“…Both of CCS and C 10 CN exhibit significant adaption toward solvent environment by giving diversified aggregated structures. Solvent exchange protocol enables the well‐defined self‐assembly of organic building blocks with minimal hydrophilicity, by which means CCS and C 10 CN with flexible alkyl chains and polar aromatic heads are capable of forming aggregates in aqueous media . To facilitate the self‐assembly, CCS and C 10 CN were predissolved in high water‐miscible solvent tetrahydrofuran (THF), which were then injected into water under the sonication.…”

Section: Resultsmentioning

confidence: 99%

Environment‐Adaptive Coassembly/Self‐Sorting and Stimulus‐Responsiveness Transfer Based on Cholesterol Building Blocks

Xing

Tham

et al. 2017

Advanced Science

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Manipulating the property transfer in nanosystems is a challenging task since it requires switchable molecular packing such as separate aggregation (self‐sorting) or synergistic aggregation (coassembly). Herein, a unique manipulation of self‐sorting/coassembly aggregation and the observation of switchable stimulus‐responsiveness transfer in a two component self‐assembly system are reported. Two building blocks bearing the same cholesterol group give versatile topological structures in polar and nonpolar solvents. One building block (cholesterol conjugated cynanostilbene, CCS) consists of cholesterol conjugated with a cynanostilbene unit, and the other one (C10CN) is comprised of cholesterol connected with a naphthalimide group having a flexible long alkyl chain. Their assemblies including gel, crystalline plates, and vesicles are obtained. In gel and crystalline plate phases, the self‐sorting behavior dominates, while synergistic coassembly occurs in vesicle phase. Since CCS having the cyanostilbene group can respond to the light irradiation, it undergoes light‐induced chiral amplification. C10CN is thermally responsive, whereby its supramolecular chirality is inversed upon heating. In coassembled vesicles, it is interestingly observed that their responsiveness can be transferred by each other, i.e., the C10CN segment is sensitive to the light irradiation, while CCS is thermoresponsive. This unprecedented behavior of the property transfer may shine a light to the precise fabrication of smart materials.

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“…Fluorescent surfactants can form micelles, vesicles, fibers, lamellas, J/H-aggregates, and other different molecular assemblies, which are highly sensitive to the variations of microenvironment, including micropolarity and microviscosity. − It was reported that a nonionic fluorescent surfactant with branched oligo(ethylene glycol) group exhibited good hydrophilic and biocompatibility. − A branched oligo(ethylene glycol) group also endows the surfactant with thermoresponsive characteristics and thus can be used as a thermosensor for sensitive detection in a large temperature range. − Besides, zwitterionic fluorescent surfactants have a similar structure to phospholipids, and thus they can bind to phospholipids and thereby label the fusion process of liposomes and specifically image cell membrane. − …”

Section: Introductionmentioning

confidence: 99%

BODIPY-Based Fluorescent Surfactant for Cell Membrane Imaging and Photodynamic Therapy

Wang

Zhao

Liu

et al. 2019

ACS Appl. Bio Mater.

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Fluorescent dyes are widely used in chemical, biological, and environmental science. However, the π–π stacking among the large π-conjugated groups of the dye molecules normally leads to the hydrophobicity and aggregation, resulting in quenching the fluorescence intensity. In the present work, a kind of BODIPY-based fluorescent surfactant C8BCOONa has been synthesized, and its self-assembly and performances in cell membrane imaging and photodynamic therapy have been studied. This fluorescent surfactant exhibits low critical micellar concentration (CMC) in aqueous solution and forms vesicles above the CMC. The fluorescence intensity of C8BCOONa significantly increases with aggregating into the DOPC vesicles, in which C8BCOONa inserts into the bilayer of DOPC vesicles through hydrophobic interaction and the intramolecular rotation of C8BCOONa is restrained in the aggregates. The fluorescent surfactant of low concentration displays negligible dark- and photocytotoxicity to MCF-7 cells and HeLa cells and can effectively stain the living cell membrane with a long retention time. Meanwhile, a large amount of reactive oxygen species is generated by higher concentration C8BCOONa under white light and brings obvious photocytotoxicity to the two types of cancer cells. Therefore, this kind of fluorescent surfactant shows a great potential in targeted bioimaging and efficient photodynamic therapy.

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Selective Metal-Ion-Mediated Vesicle Adhesion Based on Dynamic Self-Organization of a Pyrene-Appended Glutamic Acid

Cited by 16 publications

References 47 publications

Solvent‐Controlled Assembly of Aromatic Glutamic Dendrimers for Efficient Luminescent Color Conversion

Solvent‐Controlled Assembly of Aromatic Glutamic Dendrimers for Efficient Luminescent Color Conversion

Environment‐Adaptive Coassembly/Self‐Sorting and Stimulus‐Responsiveness Transfer Based on Cholesterol Building Blocks

BODIPY-Based Fluorescent Surfactant for Cell Membrane Imaging and Photodynamic Therapy

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