Circularly polarized luminescence of helically assembled pyrene π‐stacks on RNA and DNA duplexes

Nakamura, Mitsunobu; Ota, Fuyuki; Takada, Tadao; Akagi, Kazuo; Yamana, Kazushige

doi:10.1002/chir.22838

Cited by 19 publications

(10 citation statements)

References 48 publications

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“…Chiral ions or ionic molecules are attractive owing to their asymmetric catalytic activity, 1–4 enantioselectivity, 5 or their chiroptical properties 6,7 . Chiral co‐crystallization, 8 chiral molecular assemblies, 9–15 or confinement of achiral ions in chiral cyclodextrins 16 can be used to induce chiroptical properties to achiral ions or molecules and/or enhancing chiral signals with promising advantages such as (1) tunability of the chiral properties, (2) versatility of choices of chromophores (molecules, ions particles, etc. ), and (3) transparency of solutions in the UV–vis region due to the nanometric size of the assemblies.…”

Section: Introductionmentioning

confidence: 99%

Chirality induction to achiral molecules by silica‐coated chiral molecular assemblies

et al. 2021

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Section: Introductionmentioning

confidence: 99%

Chirality induction to achiral molecules by silica‐coated chiral molecular assemblies

et al. 2021

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“…The circular dichroism (CD) signals of DNA generally appear in the ultraviolet range . CPL can be induced by pyrene π-stack arrays formed on chemically modified DNA double helical structures, but laborious synthetic procedures are required to obtain this modified molecule . We hypothesized that DNA molecules would behave as a unique chiral template for fluorophore binding: that DNA’s natural chirality can be transferred to the bound dye molecules, triggering CPL activity from the coassemblies.…”

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confidence: 99%

Circularly Polarized Luminescence of Achiral Cyanine Molecules Assembled on DNA Templates

et al. 2019

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The exploration of biocompatible materials with circularly polarized luminescence (CPL) activity is becoming an attractive topic due to the great potential application in biosensing and bioimaging. Here, we describe a strategy to fabricate new CPL-active biomaterials using achiral carbazole-based biscyanine fluorophores coassembled with chiral deoxyribonucleic acid (DNA) molecules. This cyanine molecule has been shown to behave as a DNA detecting probe, featuring strong fluorescent emission induced by restriction of intramolecular rotation (RIR). When the achiral cyanine molecules are bound to the minor groove of DNA via electrostatic attraction in aqueous solution, the chirality of the DNA molecules can be transferred to the confined RIR cyanine dyes, triggering a remarkable circularly polarized luminescent emission. The chirality of the CPL signal can be regulated by the structures of the DNA templates. Stimuli-responsive CPL activates were observed from DNA–cyanine complexes. We further verified this strategy on different DNA-based nanomaterials, including DNA origami nanostructure. Our design presents a new avenue to fabricate compatible CPL materials.

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“…They include decorating inorganic quantum dots with suitable modified aminoacids, [ 27 ] and introducing pyrene π‐stack arrays formed on chemically modified DNA double helical structures. [ 28 ]…”

Section: Discussionmentioning

confidence: 99%

“…They include decorating inorganic quantum dots with suitable modified aminoacids, [27] and introducing pyrene π-stack arrays formed on chemically modified DNA double helical structures. [28] Jiang et al has recently and elegantly demonstrated the power of fabricating biological structures with CPL emissive synthetic dyes and applied the assembly for DNA sensing. [29] The rationale behind the approach is that DNA molecules can behave as unique chiral templates for fluorophores; DNA's natural chirality can be transferred to the bound dye molecules, triggering CPL activity from the assembly.…”

Section: Bioinspired Assembliesmentioning

confidence: 99%

Aggregation‐Induced Circularly Polarized Luminescence: Chiral Organic Materials for Emerging Optical Technologies

2020

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physical property differentiating two enantiomers is the direction of rotation of the polarized light. Indeed, the manipulation of polarized light, both in the absorbance and emission mode, is useful in a series of technological applications, such as liquid crystal display (LCD) panels, 3D imaging in biological systems, nonlinear optics, spintronic devices. [5-8] Progresses in the field have been boosted by the increased availability of modern spectroscopic methods. For circular dichroism (CD), which relates to ground-state properties, the commercial availability of the spectrophotometer dates back to the 1960s and has enabled in depth studies of the tertiary structure of proteins. In contrast, circularly polarized luminescence (CPL) spectrophotometers have only been recently commercially available. Nevertheless, CPL gives important additional informations, as it provides information on the excited-state, and luminescence is generally more of interest in terms of materials science and devices. [9] Emissive organic materials have been studied for decades. Among these, organic light-emitting diodes (OLEDs) have reached large-scale commercialization, since they show unique technological advantages with respect to previous technologies: energy-saving, low working voltage, high brightness, and contrast display. Polarized emission and CPL has been the subject of increasing interest. Indeed, circularly polarized OLEDs (CP-OLEDs), based on chiral organic chromophores, have been realized and reported in the recent literature. A variety of chiral organic emitters have been proposed for CPL materials. [10] Aggregation-caused quenching (ACQ) of emission is a common problem that can severely limit the performance of (chiral and achiral) fluorophores in the solid state. The field of emissive dyes has been revolutionized in the early 2000s by Tang's group, which introduced the concept, seemingly counterintuitive at the time, of aggregation-induced emission (AIE). Suitable AIE chromophores (AIEgens) can exhibit strong fluorescence emission in aggregated states, despite being nonemissive in solution. [11] The most frequent mechanism for AIE occurs when AIEgens have freely-rotating groups which, upon excitation, relax back through these rotations instead of releasing energy as light. When they aggregate or crystallize, they become emissive through restricted intramolecular rotation (RIR). Since then, the AIE field literally exploded, and several reports have started to appear on chirality-related CPL emissive dyes. [12] Chirality is becoming increasingly important in the design of organic materials with functional properties, when bulk anisotropy is needed. In the past decades, a plethora of chiral organic materials have been studied and developed. Nanostructures have brought substantial advancement to the realization of organic-molecule-based devices, and the possibilities for solid-state light emission are very promising in view of potential applications. Scientific approaches to the realization of chiral emissive materials are ...

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Circularly polarized luminescence of helically assembled pyrene π‐stacks on RNA and DNA duplexes

Cited by 19 publications

References 48 publications

Chirality induction to achiral molecules by silica‐coated chiral molecular assemblies

Chirality induction to achiral molecules by silica‐coated chiral molecular assemblies

Circularly Polarized Luminescence of Achiral Cyanine Molecules Assembled on DNA Templates

Aggregation‐Induced Circularly Polarized Luminescence: Chiral Organic Materials for Emerging Optical Technologies

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