Dynamic induction of enantiomeric excess from a prochiral azobenzene dimer under circularly polarized light

Rijeesh, K.; Hashim, P. K.; Noro, Shin Ichiro; Tamaoki, Nobuyuki

doi:10.1039/c4sc01993h

Cited by 26 publications

(13 citation statements)

References 57 publications

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“…This phenomenon is called light‐induced reversible isomerization, and its detailed mechanism, kinetics, and thermodynamics are still under investigation . The mentioned isomerization capability of these LCMs is useful and applicable in modern display technology as well as other fields such as separation and biomaterial sciences .…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of novel diazenes on a polysaccharide-based stationary phase in the reversed-phase mode

et al. 2017

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Chiral high-performance liquid chromatography separation of two recently synthesized liquid crystalline materials C1 and C2 was studied in the reversed-phase mode. Both materials have an azo-moiety and one chiral center in their molecular structures. They were available in racemic and pure S forms. For the enantiomeric separations, a Chiralpak AY-RH stationary phase based on amylose tris(5-chloro-2-methylphenylcarbamate) coated on 5 μm silica was used. The compounds were analyzed in both of their possible forms, the more thermodynamically stable E form and the labile Z form. The conditions and time scale of the UV-induced E to Z transition were briefly evaluated. Under the optimized conditions, we were able to baseline separate S and R enantiomers of both of the studied materials not only in their E forms, but also in their Z forms. In comparison to the separation in the normal-phase mode, which we have reported recently, the resolution in the reversed-phase mode is significantly better. Interestingly, peak reversal was noticed for the S and R enantiomers when the separation was carried out with E versus Z forms of both compounds.

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Section: Introductionmentioning

confidence: 99%

Chiral separation of novel diazenes on a polysaccharide-based stationary phase in the reversed-phase mode

et al. 2017

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“…In addition, the known organic molecules showing CPL are usually chiral molecules with complicated but specific structures, for example chiral helicenes, 1h , 12b , 14 which sometimes need tedious synthetic processes. Therefore, developing new molecules with more simple structures and the capability of emitting strong CPL signals becomes extremely important for constructing novel CPL devices.…”

Section: Introductionmentioning

confidence: 99%

Strong circularly polarized luminescence from the supramolecular gels of an achiral gelator: tunable intensity and handedness

et al. 2015

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“…In Fig. 2b, it is possible to appreciate the small signature on the CD measurement (less than 1 mdeg) that represents an enantiomeric excess of 0.4 % [8]. One interesting example of the generation of CP light-induced chirality, with addition of a second irradiation by CP UV ultra-violet light (CPUL) to lock the obtained configuration is showed in Fig.…”

mentioning

confidence: 92%

“…; (b) Induced CD spectra of a photoswitch molecule upon irradiation with r-CP light (blue) and l-CP light (red) at 436 nm. Reproduced from Ref [8]…”

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confidence: 99%

Perspective: plasmon antennas for nanoscale chiral chemistry

2020

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Plasmon nanoantennas are extensively used with molecular systems for the chemical and biological ultra-sensing, for boosting the molecular emissive and energy transfer properties, for the nanoscale catalysis, and for building advanced hybrid nanoarchitectures. In this Perspective we focus on the latest developments of using plasmon nanoantennas for the nanoscale chiral chemistry and for advancing the molecular magnetism. We overview the decisive role nanoplasmonics and nano-optics can play in achieving the chirally-selective molecular synthesis and separation, and in the way such processes might be precisely controlled by potentially merging chirality and magnetism at the molecular level.We give our view on how these insights might lead to the emergence of exciting new fundamental concepts in the nanoscale materials science.

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Dynamic induction of enantiomeric excess from a prochiral azobenzene dimer under circularly polarized light

Abstract: We demonstrate the simultaneous induction of chirality and enantiomeric excess from a prochiral azobenzene dimer via a chiral regioisomer formed in situ upon CPL irradiation.

Cited by 26 publications

References 57 publications

Chiral separation of novel diazenes on a polysaccharide-based stationary phase in the reversed-phase mode

Chiral separation of novel diazenes on a polysaccharide-based stationary phase in the reversed-phase mode

Strong circularly polarized luminescence from the supramolecular gels of an achiral gelator: tunable intensity and handedness

Perspective: plasmon antennas for nanoscale chiral chemistry

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