Spontaneous Deracemization of Disc‐like Molecules in the Columnar Phase

Nagayama, Hiroki; Varshney, Sanjay K.; Goto, Minoru; Araoka, Fumito; Ishikawa, Ken; Prasad, Veena; Takezoe, Hideo

doi:10.1002/anie.200904819

Cited by 39 publications

(31 citation statements)

References 28 publications

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“…Vibrational CD measurements suggested the origin of chirality in the ester linkage. Spontaneous deracemization was also observed in a disc‐like molecule in the columnar phase . The chirality is originated from a twisted disc.…”

Section: Discussionmentioning

confidence: 85%

Chiral Superstructure Mesophases of Achiral Bent‐Shaped Molecules – Hierarchical Chirality Amplification and Physical Properties

Takezoe

Araoka

2016

Advanced Materials

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Chiral mesophases in achiral bent-shaped molecules have attracted particular attention since their discovery in the middle 1990s, not only because of their homochirality and polarity, but also due to their unique physical/physicochemical properties. Here, the most intriguing results in the studies of such symmetry-broken states, mainly helical-nanofilament (HNF) and dark-conglomerate (DC) phases, are reviewed. Firstly, basic information on the typical appearance and optical activity in these phases is introduced. In the following section, the formation of mesoscopic chiral superstructures in the HNF and DC phases is discussed in terms of hierarchical chirality. Nanoscale phase segregation in mixture systems and gelation ability in the HNF phase are also described. In addition, some other related chiral phases of bent-shaped molecules are shown. Recent attempts to control such mesoscopic chiral structure and the alignment/confinement of HNFs are also discussed, along with several examples of their fascinating advanced physical properties, i.e. huge enhancement of circular dichroism, electro- and photo-tunable optical activities, chirality-induced nonlinear optics (second-harmonic-generation circular difference and electrogyration effect), enhanced hydrophobicity through the dual-scale surface morphological modulation, and photoconductivity in the HNF/fullerene binary system. Future prospects from basic science and application viewpoints are also indicated in the concluding section.

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Section: Discussionmentioning

confidence: 85%

Chiral Superstructure Mesophases of Achiral Bent‐Shaped Molecules – Hierarchical Chirality Amplification and Physical Properties

Takezoe

Araoka

2016

Advanced Materials

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“…In the early 1970s Young and co‐workers described—hidden in a report on stilbene derivates forming nematic liquid crystals—a fascinating phenomenon: the formation of optically active phases out of racemic or achiral mixtures 1. This baffling phenomenon has since then been observed in various liquid crystals ranging from banana‐shaped2 to columnar3 and nematic phases 4. In solution, similar chiral symmetry‐breaking phenomena have been observed in various self‐assembling systems.…”

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confidence: 88%

Symmetry Breaking in the Self‐Assembly of Partially Fluorinated Benzene‐1,3,5‐tricarboxamides

et al. 2012

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“…B. ein negativer Wert der Elastizitätskonstante der Biegung ( k 33 )397 und insbesondere Oberflächeneffekte,398 zunehmende Bedeutung für die Stabilisierung chiraler Überstrukturen erlangen. Der spontane Symmetriebruch auf einer supramolekularen Ebene ist einer der faszinierendsten Besonderheiten der Bent‐Core‐Mesogene, was auch die Suche nach chiralen Überstrukturen in anderen LC‐Phasen, wie in unpolaren smektischen Phasen stäbchenförmiger Moleküle (SmB und E‐Phasen),399 kolumnaren400 und kubischen Phasen,401 stimuliert hat. Insgesamt trägt die Erforschung der flüssigkristallinen Phasen von Bent‐Core‐Molekülen ganz wesentlich zum Verständnis der Chiralität in fluiden Nanostrukturen bei 377…”

Section: Bent‐core‐mesogene – Chiralität Und Polare Ordnungunclassified

Entwicklung struktureller Komplexität durch Selbstorganisation in flüssigkristallinen Systemen

Tschierske

2013

Angewandte Chemie

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Seit der Entdeckung erster Flüssigkristalle vor 125 Jahren haben sich diese zu einem Wissenschaftsgebiet mit vielseitigen Facetten entwickelt. Dieser Aufsatz beleuchtet aktuelle Entwicklungen auf diesem Gebiet mit dem Schwerpunkt auf dem molekularen Design flüssigkristalliner Materialien und ihrer Selbstorganisation. Im Fokus stehen neue und ungewöhnliche Organisationsformen mit erhöhter Komplexität, wie zelluläre Strukturen, “mehrfarbige” Kompartimentierungen, komplexe periodische und quasiperiodische Anordnungen von sphärischen Aggregaten und Nanopartikeln, sowie resultierende Phänomene wie Ferroelektrizität und Symmetriebruch. Diese werden in Zusammenhang mit anderen geordneten Strukturen in selbstorganisierten Monoschichten, in Multiblock‐Copolymeren und periodischen Nanopartikel‐Arrays diskutiert. Als Maß der strukturellen Komplexität dienen die Größe der resultierenden periodischen Gitter, der Grad der Kompartimentierung des Raumes und die “logische Tiefe” der Überstrukturen.

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Spontaneous Deracemization of Disc‐like Molecules in the Columnar Phase

Cited by 39 publications

References 28 publications

Chiral Superstructure Mesophases of Achiral Bent‐Shaped Molecules – Hierarchical Chirality Amplification and Physical Properties

Chiral Superstructure Mesophases of Achiral Bent‐Shaped Molecules – Hierarchical Chirality Amplification and Physical Properties

Symmetry Breaking in the Self‐Assembly of Partially Fluorinated Benzene‐1,3,5‐tricarboxamides

Entwicklung struktureller Komplexität durch Selbstorganisation in flüssigkristallinen Systemen

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