A Chiral Recognition System Orchestrated by Self‐Assembly: Molecular Chirality, Self‐Assembly Morphology, and Fluorescence Response

2017 ◽  
Vol 56 (41) ◽  
pp. 12518-12522 ◽  
Author(s):  
Takao Noguchi ◽  
Bappaditya Roy ◽  
Daisuke Yoshihara ◽  
Junji Sakamoto ◽  
Tatsuhiro Yamamoto ◽  
...  
Keyword(s):  
Self Assembly ◽  
Chiral Recognition ◽  
Recognition System ◽  
Fluorescence Response ◽  
Molecular Chirality

A Chiral Recognition System Orchestrated by Self‐Assembly: Molecular Chirality, Self‐Assembly Morphology, and Fluorescence Response

2017 ◽  
Vol 129 (41) ◽  
pp. 12692-12696 ◽  
Author(s):  
Takao Noguchi ◽  
Bappaditya Roy ◽  
Daisuke Yoshihara ◽  
Junji Sakamoto ◽  
Tatsuhiro Yamamoto ◽  
...  
Keyword(s):  
Self Assembly ◽  
Chiral Recognition ◽  
Recognition System ◽  
Fluorescence Response ◽  
Molecular Chirality

Self-Assembly of a Chiral Cubic Three-Connected Net from the High Symmetry Molecules C60 and SnI4

2020 ◽  
Author(s):  
Daniel B. Straus ◽  
Robert J. Cava
Keyword(s):  
Organic Synthesis ◽  
Self Assembly ◽  
Van Der Waals ◽  
Van Der Waals Forces ◽  
High Symmetry ◽  
Molecular Chirality ◽  
Chiral Materials ◽  
Self Assembled ◽  
Chiral Centers

The design of new chiral materials usually requires stereoselective organic synthesis to create molecules with chiral centers. Less commonly, achiral molecules can self-assemble into chiral materials, despite the absence of intrinsic molecular chirality. Here, we demonstrate the assembly of high-symmetry molecules into a chiral van der Waals structure by synthesizing crystals of C<sub>60</sub>(SnI<sub>4</sub>)<sub>2</sub> from icosahedral buckminsterfullerene (C<sub>60</sub>) and tetrahedral SnI4 molecules through spontaneous self-assembly. The SnI<sub>4</sub> tetrahedra template the Sn atoms into a chiral cubic three-connected net of the SrSi<sub>2</sub> type that is held together by van der Waals forces. Our results represent the remarkable emergence of a self-assembled chiral material from two of the most highly symmetric molecules, demonstrating that almost any molecular, nanocrystalline, or engineered precursor can be considered when designing chiral assemblies.

Chiral Molecular Cavities of Calix[4]Crown on Au(111)

2008 ◽  
Vol 8 (11) ◽  
pp. 5702-5707 ◽  
Author(s):  
Ge-Bo Pan ◽  
Jun Luo ◽  
Qi-Yu Zheng ◽  
Li-Jun Wan
Keyword(s):  
Self Assembly ◽  
Chiral Recognition ◽  
Scanning Tunneling ◽  
Racemic Mixture ◽  
Tunneling Microscopy ◽  
Geometrical Structures ◽  
Simple Method ◽  
Ordered Structures ◽  
Ordered Arrays ◽  
Stm Images

Well-ordered arrays of chiral molecular cavities have been constructed by self-assembly of inherently chiral calix[4]crown on Au(111) in 0.1 M HClO4 solution and investigated by scanning tunneling microscopy (STM). The chiral features are clearly observed in high resolution STM images. It is found that the adsorption of the two enantiomers results in the same ordered structures with upright orientation on Au(111). Moreover, only phase separation has been observed for the racemic mixture of the two enantiomers in the experiment. This is mainly due to the weak molecule-substrate interaction as well as asymmetric geometrical structures of the two enantiomers. The present study provides a simple method for construction of ordered arrays of chiral molecular cavities, which are of potential in chemical sensors, chiral recognition, and nonlinear optics.

scholarly journals Chirality, Gelation Ability and Crystal Structure: Together or Apart? Alkyl Phenyl Ethers of Glycerol as Simple LMWGs

Symmetry ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 732
Author(s):  
Alexander A. Bredikhin ◽  
Aidar T. Gubaidullin ◽  
Zemfira A. Bredikhina ◽  
Robert R. Fayzullin ◽  
Olga A. Lodochnikova
Keyword(s):  
Self Assembly ◽  
Chiral Recognition ◽  
Soft Materials ◽  
Gelling Agent ◽  
Low Molecular Weight ◽  
X Ray Diffraction ◽  
X Ray ◽  
Different Types ◽  
Low Molecular Weight Gelators ◽  
Phenyl Ethers

Chiral recognition plays an important role in the self-assembly of soft materials, in particular supramolecular organogels formed by low molecular weight gelators (LMWGs). Out of 14 pairs of the studied racemic and enantiopure samples of alkyl-substituted phenyl ethers of glycerol, only eight enantiopure diols form the stable gels in nonane. The formation of gels from solutions was studied by polarimetry, and their degradation with the formation of xerogels was studied by the PXRD method. The revealed crystalline characteristics of all studied xerogels corresponded to those for crystalline samples of the parent gelators. In addition to those previously investigated, crystalline samples of enantiopure para-n-alkylphenyl glycerol ethers [alkyl = pentyl (5), hexyl (6), heptyl (7), octyl (8), nonyl (9)] and racemic 3-(3,5-dimethylphenoxy)propane-1,2-diol (rac-14) have been examined by single crystal X-ray diffraction analysis. Among 22 samples of compounds 1-14 studied by SC-XRD, seven different types of supramolecular motifs are identified, of which only two are realized in crystals of supramolecular gelators. An attempt was made to relate the ability to gel formation with the characteristics of the supramolecular motif of a potential gelling agent, and the frequency of formation of the motif, required for gelation, with the chiral characteristics of the sample.

Self-Assembly and Chiral Recognition of Chiral Cationic Gemini Surfactants

Langmuir ◽  
2018 ◽  
Vol 34 (43) ◽  
pp. 12924-12933 ◽  
Author(s):  
Lili Zhou ◽  
Jiling Yue ◽  
Yaxun Fan ◽  
Yilin Wang
Keyword(s):  
Self Assembly ◽  
Chiral Recognition ◽  
Gemini Surfactants ◽  
Cationic Gemini Surfactants
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