Finite Enantiomeric Excess Nucleated in an Achiral Banana Mesogen by Chiral Alignment Surfaces

Shiromo, Kazuaki; Sahade, Daniel A.; Oda, Takuro; Nihira, Takayasu; Takanishi, Yoichi; Ishikawa, Ken; Takezoe, Hideo

doi:10.1002/anie.200461881

Cited by 31 publications

(20 citation statements)

References 26 publications

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“…The use of chiral surfaces is also effective. Shiromo et al151) synthesized a polyimide with chiral side chains, coated on both substrate surfaces and rubbed.…”

mentioning

confidence: 99%

Bent-Core Liquid Crystals: Their Mysterious and Attractive World

Takezoe¹,

Takanishi²

2006

jjap

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794

530

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Structures and properties of liquid crystalline phases formed by bent-core molecules are reviewed. At least eight phases designated as B1-B8 have been found, being unambiguously distinguished from phases formed by usual calamitic molecules due to a number of remarkable peculiarities. In addition to B1-B8 phases, smectic A-like phases and biaxial nematic phases formed by bent-core molecules are also reviewed. The most attractive aspects of this new class of liquid crystals are in polarity and chirality, despite being formed from achiral molecules. The bent-core mesogens are the first ferroelectric and antiferroelectric liquid crystals realized without introducing chirality. Spontaneous chiral deracemization at microscopic and macroscopic levels occurs and is controllable. Moreover, achiral bent-core molecules enhance system chirality. The interplay between polarity and chirality provides chiral nonlinear optic effects. Further interesting phenomena related to polarity and chirality are also reviewed.

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“…The use of chiral surfaces is also effective. Shiromo et al151) synthesized a polyimide with chiral side chains, coated on both substrate surfaces and rubbed.…”

mentioning

confidence: 99%

Bent-Core Liquid Crystals: Their Mysterious and Attractive World

Takezoe¹,

Takanishi²

2006

jjap

Self Cite

794

530

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show abstract

“…6–8,11 For example, a rich literature addresses chirality in bent-core LC systems, 10,11 and more recently, the alignment of achiral nematic LCs on chiral surfaces has also been reported. 6–8 One such study is based on the mechanical generation of meso-scale surface chirality, 7,8 where the tip of an AFM was used to scribe a chiral pattern into a polymer-coated surface.…”

Section: Discussionmentioning

confidence: 99%

“…1–5 When supramolecular assemblies exhibit long-range orientational ordering, such as seen within liquid crystalline phases, molecular details such as chirality can be amplified into mesoscopic phenomena. 6–11 At interfaces, in particular, the ordering of liquid crystals (LCs) is widely known to be remarkable for (i) the scale of interfacial energetics that controls the phenomenon (typically 10 −3 –10 −6 J/m 2 ) and (ii) the distance over which the ordering of LCs can propagate from interfaces (~100 μm or ~10 5 molecular lengths). 12,13 Inspired by the sensitivity of the ordering of LCs to the chemical functionality and organization of molecules at interfaces, a recent series of studies have examined the ordering of LCs on surfaces decorated with oligopeptides, 14–16 proteins, 17–21 DNA, 22,23 viruses 24 and other biological species displayed at surfaces.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Interactions between Liquid Crystals and Organized Monolayers of Tyrosine-Containing Dipeptides

Bai

Abbott

2011

J. Am. Chem. Soc.

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We have examined the orientational ordering of nematic liquid crystals (LCs) supported on organized monolayers of dipeptides with the goal of understanding how peptide-based interfaces encode intermolecular interactions that are amplified into supramolecular ordering. By characterizing the orientations of nematic LCs (4-cyano-4′-pentylbiphenyl (5CB) and TL205 (a mixture of mesogens containing cyclohexane-fluorinated biphenyls and fluorinated terphenyls)) on monolayers of either L-cysteine-L-tyrosine, L-cysteine-L-phenylalanine or L-cysteine-L-phosphotyrosine formed on crystallographically textured films of gold, we conclude that patterns of hydrogen bonds generated by the organized monolayers of dipeptides are transduced via macroscopic orientational ordering of the LCs. This conclusion is supported by the observation that the ordering exhibited by the achiral LCs is specific to the enantiomers used to form the dipeptide-based monolayers. The dominate role of the –OH group of tyrosine in dictating the patterns of hydrogen bonds that orient the LCs was also evidenced by the effects of phosphorylation of the tyrosine on the ordering of the LCs. Overall, these results reveal that crystallographic texturing of gold films can direct the formation of monolayers of dipeptides with long-range order, thus unmasking the influence of hydrogen bonding, chirality and phosphorylation on the macroscopic orientational ordering of LCs supported on these surfaces. These results suggest new approaches based on supramolecular assembly for reporting the chemical functionality and stereochemistry of synthetic and biological peptide-based molecules displayed at surfaces.

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“…Recently we have proposed three methods to control the chirality in achiral bent-core liquid crystal phases, in which spontaneous chiral segregation occurs [10][11][12][13]; use of chiral surface [14], CPL [15] and twisted cell geometry [16]. Particularly, the last two methods are quite effective, inducing almost 100% ee (enantiomeric excess).…”

Section: Introductionmentioning

confidence: 98%

Chirality Induced by Circularly Polarized Light in Liquid Crystalline Twin Dimers with Azo Linkages

Hoshino

Choi

Izumi

et al. 2007

Molecular Crystals and Liquid Crystals

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Emergence of large circular dichroism (CD) was found in liquid crystal twin dimers with azo linkages, nOAZmAZOn. The compounds with even m are of rod-shape and show the SmA phase, whereas those with odd m are of bent-shape and show the SmC A and B X phases. Right-and left-circular polarized light (CPL) irradiation in the crystal and B X phases induces positive and negative CD, respectively. However, large CD with the opposite sign is induced by decreasing temperature from SmC A to B X under CPL irradiation. Two different mechanisms were discussed.

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Finite Enantiomeric Excess Nucleated in an Achiral Banana Mesogen by Chiral Alignment Surfaces

Cited by 31 publications

References 26 publications

Bent-Core Liquid Crystals: Their Mysterious and Attractive World

Bent-Core Liquid Crystals: Their Mysterious and Attractive World

Enantiomeric Interactions between Liquid Crystals and Organized Monolayers of Tyrosine-Containing Dipeptides

Chirality Induced by Circularly Polarized Light in Liquid Crystalline Twin Dimers with Azo Linkages

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