Self-assembly of a poly(glutamate) dendrimer: solvent-dependent expression of molecular chirality and a [2 + 2] photocrosslinking reaction

Ikeda, Megumi; Momotake, Atsuya; Kanna, Yoko; Shimotori, Koichi; Arai, Tatsuo

doi:10.1039/c2pp25221j

Cited by 5 publications

(2 citation statements)

References 32 publications

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“…Therefore, we designed and synthesized stilbene dyad 1 ( Fig. 1a ; for synthesis and characterization, see Supplementary Methods ), in which two stilbene units can be cross-linked via a [2+2] photocycloaddition between two vinylene units in the folded conformation 34 35 36 . This photocyclization should decrease the conformational flexibility of the folded conformer ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Photoreactive helical nanoaggregates exhibiting morphology transition on thermal reconstruction

et al. 2015

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The supramolecular design of photochromic molecules has produced various smart molecular assemblies that can switch their structures and/or functions in response to light stimuli. However, most of these assemblies require large structural changes of the photochromic molecules for an efficient conversion of assembled states, which often suppresses the photoreactivity within the self-assemblies. Here we report molecular assemblies, based on a photo-cross-linkable chromophoric dyad, in which a small amount of ultraviolet-generated photochemical product can guide the entire system into different assembly processes. In apolar solution, the intact dyad self-assembles into right-handed superhelical fibrils. On ultraviolet-irradiation of these fibrils, an effective photoreaction affords a sole photo-cross-linked product. When right-handed helical fibrils, containing a minor amount of the photoproduct, are thermally reconstructed, the intact molecule and the photoproduct undergo a co-assembly process that furnishes superhelical fibrils with different molecular packing structures. This molecular design principle should afford new paradigms for smart molecular assemblies.

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Section: Resultsmentioning

confidence: 99%

Photoreactive helical nanoaggregates exhibiting morphology transition on thermal reconstruction

et al. 2015

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“…Although dendritic amphiphiles have not been frequently reported in the past decade, they exhibit some interesting assembly features with regard to the expression of chirality. − For example, aromatic rings attached to the core of a dendron with chiral glutamic acid substituents can show strong CD signals in their absorption regions via self-assembly, which means the chirality can be transferred from the periphery to the core and the whole assembly. A helical tube fabricated from a dendritic glutamide lipid ( 21 ) exhibited a wall with a thickness of 4 nm, which corresponds to a bilayer thickness (Figure ).…”

Section: Supramolecular Chirality In Self-assembled Systems Containin...mentioning

confidence: 99%

Supramolecular Chirality in Self-Assembled Systems

2015

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Scissor‐Shaped Photochromic Dyads: Hierarchical Self‐Assembly and Photoresponsive Property

Tashiro

Saito

Arima

et al. 2021

The Chemical Record

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Unique relationships between hierarchically organized biological nanostructures and functions have motivated chemists to construct sophisticated artificial nanostructured systems from small and simple synthetic molecules through self-assembly. As one of such sophisticated systems, we have investigated scissor-shaped photochromic dyads that can hierarchically selfassemble into discrete nanostructures showing photoresponsive properties. We synthesized various azobenzene dyads and found that these dyads adopt intramolecularly folded conformation like a closed scissor, and then self-assemble into toroidal nanostructures by generating curvature. The toroids further organize into nanotubes and further into helical supramolecular fibers depending on the nature of alkyl substituents. All of these nanostructures can be dissociated and reorganized through the photoisomerization of azobenzene units. On the other hand, the introduction of stilbene chromophores instead of azobenzenes leads to onedimensional supramolecular polymerization, which upon the intramolecular photocyclization of stilbene chromophores shifts to curved self-assembly leading to helicoidal fibers with distinct supramolecular chirality.

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Self-assembly of a poly(glutamate) dendrimer: solvent-dependent expression of molecular chirality and a [2 + 2] photocrosslinking reaction

Cited by 5 publications

References 32 publications

Photoreactive helical nanoaggregates exhibiting morphology transition on thermal reconstruction

Photoreactive helical nanoaggregates exhibiting morphology transition on thermal reconstruction

Supramolecular Chirality in Self-Assembled Systems

Scissor‐Shaped Photochromic Dyads: Hierarchical Self‐Assembly and Photoresponsive Property

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