Chiroptical switch based on azobenzene-substituted polydiacetylene LB films under thermal and photic stimuli

Zou, Gang; Jiang, Hao; Zhang, Qijin; Kohn, Hideki; Manaka, Takaaki; Iwamoto, Mitsumasa

doi:10.1039/b913764e

Cited by 56 publications

(50 citation statements)

References 58 publications

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“…[6,7,[11][12][13] On the basis of our experimental data, we could propose a possible explanation for our interesting mechanically induced chirality selection phenomenon observed in the interfacial systems, as shown in Scheme 1. At the earlier stage of the compression (%2 mNm À1 , Scheme 1 a), some of the molecules are stochastically organized to form chiral assemblies with predominantly P-or M-helical folding configurations in an unpre- dictable manner.…”

Section: Resultsmentioning

confidence: 98%

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Left or Right? The Direction of Compression‐Generated Vortex‐Like Flow Selects the Macroscopic Chirality of Interfacial Molecular Assemblies

Chen

et al. 2011

Chemistry A European J

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A new method is described through which the macroscopic chirality of interfacial molecular assemblies of an achiral porphyrin can be mechanically controlled using an original yet efficient Langmuir-Blodgett (LB) technique. By using the unilateral compression geometry, we find that the assemblies deposited from the mirror regions of the LB trough display mirror macroscopic chirality. It is indicated that vortex-like flows could be generated during compression, and that it is the direction of this compression-generated vortex-like flow that determine the macroscopic chirality of the formed assemblies. Moreover, the standard sample-fabrication method with bilateral compression geometry is reformed, and we find that the samples formulated around the left-hand- and right-hand-side Langmuir barriers display opposite macroscopic chiralities. The results suggest that mechanically controlled supramolecular chirogenesis could be efficiently realized through such an LB technique. The investigation establishes a new forum for further investigation of the mechanically induced preferred supramolecular chirality in terms of interfacial organization, and provides the old LB technique with new opportunities for controlling the macroscopic chirality of a supramolecular system that is wholly composed of achiral units.

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Section: Resultsmentioning

confidence: 98%

“…searchers found similar results during recent investigations. [13] It has been suggested that stochastic symmetry breaking is responsible for this interesting phenomenon. [11][12][13] However, it remains a great challenge to control the macroscopic chirality of these systems.…”

Section: Introductionmentioning

confidence: 99%

Left or Right? The Direction of Compression‐Generated Vortex‐Like Flow Selects the Macroscopic Chirality of Interfacial Molecular Assemblies

Chen

et al. 2011

Chemistry A European J

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“…They can also be rapidly photopolymerized by UV illumination to produce polydiacetylenes bearing azobenzene-containing side chains on the rigid conjugated backbones, which resemble the structure of rigid templates decorated with closely-packed photochromic units. Previous efforts on azobenzene-decorated diacetylenes and polydiacetylenes have focused on asymmetric structures where azobenzene groups functionalized on one side and long alkyl chains on the other side are designed to enable the selfassembly of molecules into vesicles and tubes 25 or bilayer lms 26,27 for applications such as photocontrolled molecular recognition and reversible optical switch. 28 Building upon the knowledge gained in these studies regarding the structural change of the azobenzene-functionalized diacetylenes, we are able to design symmetric diacetylenes that enable the high loading and ordered arrangement of azobenzene groups.…”

Section: Organicmentioning

confidence: 99%

Photon energy storage materials with high energy densities based on diacetylene–azobenzene derivatives

et al. 2016

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Photocontrolled self-assembly of molecules has been utilized to change the physical properties of organic materials for various applications, while photon energy storage materials that incorporate photochromic molecules such as azobenzenes have been recognized as another highly attractive class of materials that convert and store photon energy in the strained chemical bonds. Herein, we demonstrate the photocontrolled self-assembly and disassembly of photon energy storage materials based on new diacetylene derivatives with azobenzene moieties and with varied alkyl spacers and linkers. We

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“…As can be seen, the asymmetric polymerization kinetics constant k 1 exhibited quadratic dependence on the light intensity of LPL, where the slop of the plots was about 2. All above results revealed that the formation mechanism of the helical PDA chains may involve biradical mechanism (the biradical dimer acted as the initiator in the DA polymerization process 26 ) as the primary species, similar as that on irradiation with CPL 27 . ARTICLE It has been reported that the photoinitiation of polymerization reaction depends on the excitation of DA monomers.…”

Section: Resultsmentioning

confidence: 79%

Enantioselective synthesis of helical polydiacetylene by application of linearly polarized light and magnetic field

et al. 2014

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Magnetic optical activity, which can occur in all media and is induced by longitudinal magnetic field, causes the difference in absorption coefficients of left and right circularly polarized light and has the potential for magnetically induced enantioselectivity in chemical reactions. Compared with the well-established technique with circularly polarized light, there are few reports on the production of helical conjugated polymers in a photochemical reaction based on above magnetochiral anisotropy mechanism. Herein, we demonstrate experimentally that the enantioselective polymerization of diacetylene derivative can be achieved in the liquid crystal phase by application of linearly polarized light under a parallel or antiparallel magnetic field. The screw direction of predominant helical polydiacetylene chain can be rigorously controlled with the relative orientation of linearly polarized light and the magnetic field. Moreover, the prepared helical polydiacetylene assemblies can serve as a direct visual probe for the enantioselective recognition of D-or L-lysine.

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Chiroptical switch based on azobenzene-substituted polydiacetylene LB films under thermal and photic stimuli

Cited by 56 publications

References 58 publications

Left or Right? The Direction of Compression‐Generated Vortex‐Like Flow Selects the Macroscopic Chirality of Interfacial Molecular Assemblies

Left or Right? The Direction of Compression‐Generated Vortex‐Like Flow Selects the Macroscopic Chirality of Interfacial Molecular Assemblies

Photon energy storage materials with high energy densities based on diacetylene–azobenzene derivatives

Enantioselective synthesis of helical polydiacetylene by application of linearly polarized light and magnetic field

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