Design and Fabrication of a Flexible and Self‐Supporting Supramolecular Film by Hierarchical Control of the Interaction between Hydrogen‐Bonded Sheet Assemblies

Yoshikawa, Isao; Li, Jun; Sakata, Yuka; Araki, Koji

doi:10.1002/anie.200352641

Cited by 43 publications

(19 citation statements)

References 26 publications

(7 reference statements)

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“…Nevertheless, only a limited number of reports have appeared so far regarding selfsupporting and flexible films. [6][7][8][9] Several non-covalent polymers formed through complementary molecular groups exhibit characteristic of conventional polymers while feature reversibility in the bonding between macromer units. [10] However, controlling the secondary (and higher) structures of non-covalent polymers still remains a challenging task.…”

Section: Introductionmentioning

confidence: 99%

Self‐supporting Polymer from a POSS Derivative

Cheng

Yen

Chang

2011

Macromol. Rapid Commun.

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A new polyhedral oligomeric silsesquioxane macromer, octakis[N‐(6‐aminopyridin‐2‐yl)undecanamide‐10‐dimethyl‐siloxy]silsesquioxane (POSS‐C11‐Py), containing eight diaminopyridine arms, is able to self‐assemble to form a physically crosslinked polymer‐like structure with good mechanical properties (tensile strength = 46.1 MPa, tensile modulus = 0.58 GPa, elongation = 49.3%) through quadruple hydrogen bonding interactions between these arms. POSS‐C11‐Py is the first organic/inorganic supermolecule possessing polymer‐like mechanical properties as a result of self‐complementary interactions, providing a potential route toward the design and fabrication of polymer‐like supramolecular materials. magnified image

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Section: Introductionmentioning

confidence: 99%

Self‐supporting Polymer from a POSS Derivative

Cheng

Yen

Chang

2011

Macromol. Rapid Commun.

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“…1b), representing the second example of a supramolecular gel film formed through aggregation of LMOGs. [13] The ferrocenyl group is easy to oxidize both chemically and electrochemically. [8,14] Accordingly, an equal amount (in moles) of (NH 4 ) 2 Ce(NO 3 ) 6 dissolved in a minimum amount of H 2 O was carefully placed above the gel of 1/cyclohexane, and it was found that the gel gradually turned into a dark green suspension.…”

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confidence: 99%

An Organometallic Super‐Gelator with Multiple‐Stimulus Responsive Properties

et al. 2008

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Stimulus-responsive gels have recently attracted widespread attention as new functional materials for potential applications in sensors, [1] actuators, [2] shape memories, [3] drug delivery devices, [4] and displays. [5] One of the promising properties that organogels based on low molecular mass organic gelators (LMOGs) can offer is their reversible sol-gel phase transition as a result of external stimuli. [6] As far as we know, redoxresponsive organogels from LMOGs, however, are limited. Shinkai and coworkers [7a] reported the first example of organogels of this kind, which contains a redox-active Cu I / Cu II center. Besides, they also synthesized a series of quater-, quinque-, and sexithiophene derivatives bearing two cholesteryl moieties at the a-position. It was found that a sol-gel phase transition can be implemented by addition of oxidizing and reducing reagents.[7b] Zhu and colleagues [7c] prepared an electro-active LMOG containing a tetrathiafulvalene (TTF) entity. The gel formation can be tuned by means of oxidation/ reduction of the TTF group chemically or electrochemically. Although these gel systems are redox responsive, their properties, such as mechanical strength, flexibility, and sensitivity to external stimulus, are far from those required for practical uses. Therefore, creating instant, reversible, redox-responsive, and mechanically flexible organogels still remains a challenge. As a remarkable organometallic compound, ferrocene (Fc) contains an oxidizable metal ion, Fe II , and is a nonpolar compound in the neutral state, and thereby it dissolves readily in hydrocarbon solvents. This property, however, can be easily reversed by simple oxidation of the central ion. Our interest in stimulus-responsive supramolecular gel systems led us to consider the compound as a neutral-cation redox pair that may be employed to tune the gelling ability of a gelator containing it. Actually, the same idea has been adopted by a number of groups for studies of switchable complexation and molecular aggregation in micelles and vesicles. [8] However, all compounds containing the apolar ferrocenyl or charged ferrocenium moiety reported so far do not result in gelation, as documented for a number of solvents. [8b,8c] Introduction of metal ions is a practical way of giving organogels some smart properties.[9] For example, Sijbesma and coworkers [9a] designed and prepared two chloroform gels with reported a palladium-based organometallic LMOG that is able to catalyze C-C bond formation even in the gel state. We report here four novel cholesterol-appended ferrocene derivatives ( Fig. 1a; see Supporting Information for preparation details), and present first evidence for the gelation ability of organometallic compounds of this kind, and particularly the unusual redox-, mechanical-, and ultrasonic-controllable sol-gel phase transition phenomena. These gelators contain one redox-active ferrocenyl moiety and one cholesteryl residue linked by different diamino units. This design was chosen on the basis of the analys...

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“…Different from the dipeptide-based derivatives reported earlier, these compounds are organic acids (65)(66)(67)(68)(69)(70)(71)(72)(73)(74)(75)(76)(77)(78)(79)(80), and possess phase-selective gelation ability of gelating organic solvents from their biphasic mixtures with water. Interestingly, the sodium salts of some of the dipeptide derivatives (69a, 75a, 77a, 78a, and 79a) only gel the aqueous phase of the mixture solvents via the heating-cooling cycle.…”

Section: Phase-selective Gelationmentioning

confidence: 97%

“…[64][65][66][67][68]. However, small molecules of the above mentioned film formation properties have not shown gelation properties as LMMGs do [69,70]. Recently, Fang and co-workers are lucky to find a small number of LMMGs which show both gelation and film formation properties [28].…”

Section: Supramolecular Gel Filmsmentioning

confidence: 99%

Progress in the studies of low-molecular mass gelators with unusual properties

Liu

Fang

2011

Sci. China Chem.

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This article is intended to provide an overview of recent progress in the studies of cholesterol-based low-molecular mass gelators (LMMGs) with unusual properties, in particular, gelation and selective gelation at room temperature, gel emulsions and gel film formation, etc. Potential applications of the LMMGs in spilled oil collection and water purification are briefly presented.gelation at room temperature, selective gelation, gel emulsions, gel films

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Design and Fabrication of a Flexible and Self‐Supporting Supramolecular Film by Hierarchical Control of the Interaction between Hydrogen‐Bonded Sheet Assemblies

Cited by 43 publications

References 26 publications

Self‐supporting Polymer from a POSS Derivative

Self‐supporting Polymer from a POSS Derivative

An Organometallic Super‐Gelator with Multiple‐Stimulus Responsive Properties

Progress in the studies of low-molecular mass gelators with unusual properties

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