Shaping self-assembling small molecules into fibres by melt electrospinning

Singer, Julia C.; Giesa, Reiner; Schmidt, Hans‐Werner

doi:10.1039/c2sm26469b

Cited by 21 publications

(21 citation statements)

References 43 publications

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“…Starting at a T sp = 300 °C in its N c phase, fibers were obtained with diameters of d fib = 2.8 ± 0.8 μm. Electrospinning in its isotropic phase at 330 °C led to thinner fibers with d fib = 2.0 ± 0.6 μm …”

Section: Resultsmentioning

confidence: 99%

“…For the melt electrospinning experiments, a custom‐designed apparatus was used (see Scheme ) similar to the one described before . The substances were filled as powder into a 1 mL Fortuna‐Optima syringe with luer glass tip (Poulten & Graf).…”

Section: Methodsmentioning

confidence: 99%

“…At an even higher temperature of 300 °C, the amount of spheres increases and the formation of fibers is suppressed (Table S1). The presence of fibers from the melt is feasible since the optical isotropic phase still consists of short columnar pre‐aggregates which are strong enough to interact with the applied electric field …”

Section: Methodsmentioning

confidence: 99%

“…For the melt electrospinning experiments, a custom-designed apparatus was used (see Scheme 1) similar to the one described before. [22] The substances were filled as powder into a 1 mL Fortuna-Optima syringe with luer glass tip (Poulten & Graf). Mounted to this tip with a high temperature adhesive was a hypodermic 20 G (inner diameter: 0.6 mm) metal needle shortened to 1 mm.…”

Section: Spinning Setupmentioning

confidence: 99%

“…[13] Recently, we reported for the first time on the melt electrospinning of 1,3,5-benzene-and 1,3,5-cyclohexanetrisamides into long and homogenous fibers. [22,23] Depending on core structure, amide connectivity to the core, and peripheral substituents, trisamides can exhibit thermotropic behavior and form mesophases. [24][25][26][27] In the solid state, as well as in dilute non-polar solutions, these organic molecules self-assemble into one-dimensional nanosized rod-like structures stabilized by three hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

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Melt Electrospinning of Small Molecules

Singer

Ringk

Giesa

et al. 2015

Macro Materials & Eng

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Electrospinning is an attractive way to prepare nano‐ and macrofibers. It was demonstrated by our group that trisamides can be melt electrospun into supramolecular fibers. To establish structure–property relationships regarding spinnability and morphology, melt electrospinning experiments were conducted using several classes of compounds. The number of hydrogen bonds was systematically decreased from three for trisamides, to two for bisamide and sorbitols, and to zero for perylene bisimides and tertiary trisamides. As a result, trisamides are readily spun into fibers, whereas for bisamides and sorbitols mainly electrospraying into spheres is observed. Perylene bisimides form well‐defined fibers due to strong π–π interactions. This supramolecular fiber is interesting for many scientific disciplines.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Spinning Setupmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Melt Electrospinning of Small Molecules

Singer

Ringk

Giesa

et al. 2015

Macro Materials & Eng

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Electrospinning Parameters and Resulting Nanofiber Characteristics

Tang¹,

Levit²,

Swana³

et al. 2022

Applications of Polymer Nanofibers

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Photoresponsive Hydrogen‐Bonded Supramolecular Polymers Based on a Stiff Stilbene Unit

Chen

et al. 2013

Angewandte Chemie

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Supramolecular polymers are arrays of low-molecular-weight building blocks held together by hydrogen bonding or other reversible noncovalent interactions. [1] They have attracted increasing attention recently because of their potential applications in the fabrication of smart functional materials whose physical properties and functions could be controlled by external stimuli. [2] Among such stimuli, light is especially attractive as it allows remote activation and control with submicrometer spatial and sub-millisecond temporal resolution without generating waste chemicals. [3] Previously reported supramolecular polymers have been shown to polymerize/ depolymerize [4] as well as switch between welldefined aggregation states [5] or gel and solution [6] upon irradiation. Azobenzene (AB) is the most commonly used chromophore in photoresponsive polymers because of the large structural difference between its E and Z isomers. However, the halflife of most (Z)-AB derivatives at room temperature is a few hours, [7] which makes polymers of pure (Z)-AB hard to prepare and study. This has so far made it difficult to exploit the (probable) differences in the physical properties and polymerization mechanisms between the two isomeric states of AB polymers.A stiff stilbene (1,1-biindane, Scheme 1) moiety offers considerable advantages over AB as a chromophore for photoresponsive supramolecular polymers. Similar to AB, stilbene exists as structurally distinct E and Z isomers. Unlike AB, the isomers are separated by an activation barrier of about 43 kcal mol À1 (i.e., a half-life of ca. 10 9 years at 300 K), thus making thermal isomerization negligibly slow at temperatures below about 420 K. [8a] The photoisomerization of either isomer of the stiff stilbene derivative proceeds with 50 % quantum yield, [8d] compared to about 20 % (l < 320 nm) or 35 % (l > 400 nm) for the photoisomerization of (E)azobenzene to the Z isomer. [8e] The stiff stilbene offers greater opportunities for peripheral substitution than AB while being generally more inert. Boulatov et al. has used the stiff stilbene moiety extensively as a molecular force probe to mimic the strain generated in diverse functional groups when they are part of a stretched polymer. [8] Herein, we report a photoresponsive supramolecular polymer comprised of quadruply hydrogen-bonded monomers of stiff stilbene with two ureidopyrimidinone moieties (Scheme 1). The selfassembly behavior and physical properties of the supramolecular polymers can be regulated by photoisomeirization of stiff stilbene. (Z)-1 and (E)-1 polymerize by ring-chain and isodesmic growth mechanisms, respectively. The polymer of Scheme 1. Photoisomerization of the UPy-linked stiff stilbene derivates (Z)-1 and (E)-1.

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Shaping self-assembling small molecules into fibres by melt electrospinning

Cited by 21 publications

References 43 publications

Melt Electrospinning of Small Molecules

Melt Electrospinning of Small Molecules

Electrospinning Parameters and Resulting Nanofiber Characteristics

Photoresponsive Hydrogen‐Bonded Supramolecular Polymers Based on a Stiff Stilbene Unit

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