Topochemical polymerization of dumbbell-shaped diacetylene monomers: relationship between chemical structure, molecular packing structure, and gelation property

Kim, Dae‐Yoon; Lee, Sang‐Ah; Jung, Daseal; Koo, Jahyeon; Yu, Yeon–Tae; Lee, Cheul-Ro; Jeong, Kwang‐Un

doi:10.1039/c7sm01166k

Cited by 20 publications

(16 citation statements)

References 53 publications

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“…The gelation process is performed by heating the sample in a screw-capped vial and subsequently cooling to room temperature. , 1AZ3BP asymmetric macrogelator can immobilize the organic solvents (cyclohexane and methanol with 3 wt % 1AZ3BP) and forms a very stable organogel under ambient conditions even for several months (Figure a). The gelation capabilities of 1AZ3BP in other organic solvents are summarized in Table S1.…”

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confidence: 99%

Azobenzene Molecular Machine: Light-Induced Wringing Gel Fabricated from Asymmetric Macrogelator

et al. 2018

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To develop light-triggered wringing gels, an asymmetric macrogelator (1AZ3BP) was newly synthesized by the chemically bridging a photoisomerizable azobenzene (1AZ) molecular machine and a biphenyl-based (3BP) dendron with a 1,4-phenylenediformamide connector. 1AZ3BP was self-assembled into a layered superstructure in the bulk state, but 1AZ3BP formed a three-dimensional (3D) network organogel in solution. Upon irradiating UV light onto the 3D network organogel, the solvent of the organogel was squeezed and the 3D network was converted to the layered morphology. It was realized that the metastable 3D network organogels were fabricated mainly due to the nanophase separation in solution. UV isomerization of 1AZ3BP provided sufficient molecular mobility to form strong hydrogen bonds for the construction of the stable layered superstructure. The light-triggered wringing gels can be smartly applied in remote-controlled generators, liquid storages, and sensors.

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confidence: 99%

Azobenzene Molecular Machine: Light-Induced Wringing Gel Fabricated from Asymmetric Macrogelator

et al. 2018

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“…The lower frequencies in the case of ADA Y‐phase are indicative of weaker NH bond likely due to hydrogen bonding between the NH units and carbonyl oxygen in adjacent aminoanthraquinones residues. [ 45,54 ] The FTIR shifts indicate close proximity of anthraquinone units in ADA Y‐phase in a face‐to‐face fashion which allows the aminoanthraquinone headgroups to form hydrogen bonding. Importantly, thermal treatment of the R‐phase (heating at 80 °C) resulted in shifts of the FTIR peaks toward the spectral positions of the Y‐phase.…”

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confidence: 99%

Aggregation‐Dependent Chromism and Photopolymerization of Aminoanthraquinone‐Substituted Diacetylenes

Bisht

Dhyani

Jelinek

2020

Advanced Optical Materials

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Polydiacetylenes have attracted significant interest for their unique chromatic properties and applications in sensing, imaging, and optics. Here, it is demonstrated that aminoanthraquinone‐substituted diacetylenes exhibit distinct aggregation‐dependent chromatic properties, affected by the alignment of both the aminoanthraquinone headgroups and diacetylene sidechains. Specifically, it is shown that aminoanthraquinone‐diacetylene monomers adopt different film organizations depending upon the polarity of the solvent employed for predissolution. In particular, a yellow aminoanthraquinone‐diacetylene phase, which undergoes photopolymerization upon ultraviolet irradiation, is produced upon dissolution in polar organic solvents prior to deposition and drying on solid substrates. In contrast, a red phase that can not be polymerized is observed when the monomers are predissolved in apolar solvents. Microscopic and spectroscopic analyses indicate that the optical properties of the films are determined by the degree of overlap between the aminoanthraquinone headgroups as well as the alignment of the diacetylene sidechains; both factors are intimately affected by interactions of the monomers with solvent molecules. It is shown that the aggregation‐dependent diacetylene films exhibit remarkable solvochromic, thermochromic, and mechanochromic properties. The aminoanthraquinone‐substituted diacetylenes may facilitate chromatic tuning of polydiacetylene systems in the solid state, determined by solvent‐ and intermolecular interactions and concomitant self‐assembly of the pendant sidechains and aromatic headgroups.

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“…As shown in Scheme , the rigid biphenyl‐based LC dendron (R) with amphiphilic flexible side chains (hydrophobic alkyl and hydrophilic ethylene oxide chains) were chemically linked to C 60 . To assist the construction of hierarchical nanostructures of C 60 D, the pyrene‐based tweezer‐like asymmetric dendron (PD) with three biphenyl‐based LC groups was additionally prepared . Owing to distinct natures between the amphiphilic dendrons and the π‐conjugated C 60 , C 60 D can exhibit strong nanophase separation at molecular scale and tend to form into a layer structure .…”

Section: Resultsmentioning

confidence: 99%

Programmed Hierarchical Hybrid Nanostructures from Fullerene‐Dendrons and Pyrene‐Dendrons

Park

Kang

Yoon

et al. 2018

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The construction of fullerene (C60) hierarchical nanostructures with the help of amphiphilic molecules remains a challenging task in nanoscience and nanotechnology. Utilizing the host–guest complex concept, sub‐10 nm layered superstructures are constructed from a monofunctionalized C60 dendron (C60D, guest) and tweezer‐like pyrene dendron (PD, host). Since C60D and PD are asymmetric shape amphiphiles having liquid crystal (LC) dendrons, both C60D and PD construct head‐to‐head bilayer superstructures by themselves. From fluorescence titration experiments, it is realized that the host–guest complex shows 1:1 stoichiometric binding with a binding constant (Ksv = 2.45 × 105m−1). Based on the morphological observations and scattering analyses, it is found that buckle‐like asymmetric building blocks (C60D·PD) are self‐assembled by the host–guest complex and construct multilayer hybrid nanostructures. The hierarchical hybrid nanostructures consist of the self‐assembled C60D·PD bilayer with a 2D C60·P nanoarray sandwiched between LC dendrons. This advanced strategy is expected to be a practicable and rational guideline for the fabrication of programmed hierarchical hybrid nanostructures.

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Topochemical polymerization of dumbbell-shaped diacetylene monomers: relationship between chemical structure, molecular packing structure, and gelation property

Cited by 20 publications

References 53 publications

Azobenzene Molecular Machine: Light-Induced Wringing Gel Fabricated from Asymmetric Macrogelator

Azobenzene Molecular Machine: Light-Induced Wringing Gel Fabricated from Asymmetric Macrogelator

Aggregation‐Dependent Chromism and Photopolymerization of Aminoanthraquinone‐Substituted Diacetylenes

Programmed Hierarchical Hybrid Nanostructures from Fullerene‐Dendrons and Pyrene‐Dendrons

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