Synthesis and self-assembly of halogen-bond donor–spacer–hydrogen-bond donor molecules: polymeric liquid crystals induced by combination of intermolecular halogen- and hydrogen-bonding interactions

2012 ◽  
Vol 40 (2) ◽  
pp. 185-196 ◽  
Author(s):  
Ching Mui Cho ◽  
Xiaobai Wang ◽  
Jason Jiesheng Li ◽  
Chaobin He ◽  
Jianwei Xu
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Liquid Crystals ◽  
Self Assembly ◽  
Halogen Bond ◽  
Hydrogen Bond Donor ◽  
Polymeric Liquid ◽  
Hydrogen Bonding Interactions ◽  
Polymeric Liquid Crystals

scholarly journals Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid

Crystals ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 198
Author(s):  
Nucharee Chongboriboon ◽  
Kodchakorn Samakun ◽  
Winya Dungkaew ◽  
Filip Kielar ◽  
Mongkol Sukwattanasinitt ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Phase Transitions ◽  
Self Assembly ◽  
Solid Phase ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Cooperative Effect ◽  
Hydrogen Bonding Interactions ◽  
Solvent Molecules

Halogen bonding is one of the most interesting noncovalent attractions capable of self-assembly and recognition processes in both solution and solid phase. In this contribution, we report on the formation of two solvates of tetrabromoterephthalic acid (H2Br4tp) with acetonitrile (MeCN) and methanol (MeOH) viz. H2Br4tp·2MeCN (1MeCN) and H2Br4tp·2MeOH (2MeOH). The host structures of both 1MeCN and 2MeOH are assembled via the occurrence of simultaneous Br···Br, Br···O, and Br···π halogen bonding interactions, existing between the H2Br4tp molecular tectons. Among them, the cooperative effect of the dominant halogen bond in combination with hydrogen bonding interactions gave rise to different supramolecular assemblies, whereas the strength of the halogen bond depends on the type of hydrogen bond between the molecules of H2Br4tp and the solvents. These materials show a reversible release/resorption of solvent molecules accompanied by evident crystallographic phase transitions.

scholarly journals An Investigation of Five Component [3+2] Self-Assembled Cage Formation Using amidinium...carboxylate Hydrogen Bonds

2021 ◽  
Author(s):  
Chriso Thomas ◽  
Emer Foyle ◽  
Samuel Walker ◽  
Nicholas White
Keyword(s):  
Hydrogen Bond ◽  
Self Assembly ◽  
Solvent Mixtures ◽  
Hydrogen Bond Donor ◽  
Cage Structure ◽  
Hydrogen Bond Acceptor ◽  
X Ray ◽  
Hydrogen Bonding Interactions ◽  
The Individual ◽  
And Diffusion

The assembly of hydrogen bonded cages using amidinium∙∙∙carboxylate hydrogen bonding interactions was investigated. A new tris-amidinium hydrogen bond donor tecton based on a tetraphenylmethane scaffold was prepared and its self–assembly with the terephthalate anion studied, and a new tricarboxylate hydrogen bond acceptor tecton was synthesized and its assembly with the 1,3-benzenebis(amidinium) hydrogen bond donor explored. In both cases, molecular modelling indicated that the formation of the cages was geometrically feasible and 1H NMR spectroscopic evidence was consistent with interactions between the components in competitive d6- DMSO solvent mixtures. DOSY NMR spectroscopy of both systems indicated that both components diffuse at the same rate as each other, and diffusion coefficients were consistent with cage formation, and with the formation of assemblies significantly larger than the individual components. An X-ray crystal structure showed that one of the assemblies did not have the desired cage structure in the solid state

Halogen-bond and hydrogen-bond interactions between three benzene derivatives and dimethyl sulphoxide

2014 ◽  
Vol 16 (15) ◽  
pp. 6946-6956 ◽  
Author(s):  
Yan-Zhen Zheng ◽  
Nan-Nan Wang ◽  
Yu Zhou ◽  
Zhi-Wu Yu
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Computational Methods ◽  
Halogen Bond ◽  
Dimethyl Sulphoxide ◽  
Benzene Derivatives ◽  
Hydrogen Bond Interactions ◽  
Hydrogen Bonding Interactions

We examine and compare the halogen- and hydrogen-bonding interactions between benzene derivatives and DMSO by experimental and computational methods.

scholarly journals An Investigation of Five Component [3+2] Self-Assembled Cage Formation Using amidinium...carboxylate Hydrogen Bonds

2021 ◽  
Author(s):  
Chriso Thomas ◽  
Emer Foyle ◽  
Samuel Walker ◽  
Nicholas White
Keyword(s):  
Hydrogen Bond ◽  
Self Assembly ◽  
Solvent Mixtures ◽  
Hydrogen Bond Donor ◽  
Cage Structure ◽  
Hydrogen Bond Acceptor ◽  
X Ray ◽  
Hydrogen Bonding Interactions ◽  
The Individual ◽  
And Diffusion

The assembly of hydrogen bonded cages using amidinium∙∙∙carboxylate hydrogen bonding interactions was investigated. A new tris-amidinium hydrogen bond donor tecton based on a tetraphenylmethane scaffold was prepared and its self–assembly with the terephthalate anion studied, and a new tricarboxylate hydrogen bond acceptor tecton was synthesized and its assembly with the 1,3-benzenebis(amidinium) hydrogen bond donor explored. In both cases, molecular modelling indicated that the formation of the cages was geometrically feasible and 1H NMR spectroscopic evidence was consistent with interactions between the components in competitive d6- DMSO solvent mixtures. DOSY NMR spectroscopy of both systems indicated that both components diffuse at the same rate as each other, and diffusion coefficients were consistent with cage formation, and with the formation of assemblies significantly larger than the individual components. An X-ray crystal structure showed that one of the assemblies did not have the desired cage structure in the solid state

Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts

2015 ◽  
Vol 13 (9) ◽  
pp. 2582-2587 ◽  
Author(s):  
Stuart P. Cornes ◽  
Charles H. Davies ◽  
David Blyghton ◽  
Mark R. Sambrook ◽  
Paul D. Beer
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Anion Recognition ◽  
Dihydrogen Phosphate ◽  
Donor Group ◽  
Hydrogen Bond Donor

A [2]rotaxane anion host that switches selectivity from dihydrogen phosphate to the halides upon substituting a hydrogen bond donor group for a halogen bond donor group within the axle component is described.

Lyotropic polymeric liquid crystals

1983 ◽  
Vol 80 ◽  
pp. 25-30 ◽  
Author(s):  
E.T. Samulski ◽  
D.B. Dupré
Keyword(s):  
Liquid Crystals ◽  
Polymeric Liquid ◽  
Polymeric Liquid Crystals

Shrinkage of blends of amorphous polymers with polymeric liquid crystals

1989 ◽  
Vol 23 (1) ◽  
pp. 253-263 ◽  
Author(s):  
E. Amendola ◽  
C. Carfagna ◽  
L. Nicodemo ◽  
M. R. Nobile
Keyword(s):  
Liquid Crystals ◽  
Amorphous Polymers ◽  
Polymeric Liquid ◽  
Polymeric Liquid Crystals

scholarly journals Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-κN3)cobalt(II) pentahydrate

2009 ◽  
Vol 65 (6) ◽  
pp. m702-m702 ◽  
Author(s):  
Wen-Dong Song ◽  
Hao Wang ◽  
Shi-Jie Li ◽  
Pei-Wen Qin ◽  
Shi-Wei Hu
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Organic Ligand ◽  
Octahedral Geometry ◽  
Mononuclear Complex ◽  
Distorted Octahedral Geometry ◽  
Water Molecules ◽  
Supramolecular Network ◽  
Hydrogen Bonding Interactions ◽  
Distorted Octahedral

In the title mononuclear complex, [Co(C9H4N2O4)(H2O)5]·5H2O, the CoIIatom exhibits a distorted octahedral geometry involving an N atom of a 1H-benzimidazole-5,6-dicarboxylate ligand and five water O atoms. A supramolecular network is generated through intermolecular O—H...O hydrogen-bonding interactions involving the coordinated and uncoordinated water molecules and the carboxyl O atoms of the organic ligand. An intermolecular N—H...O hydrogen bond is also observed.

scholarly journals Machine learning models for hydrogen bond donor and acceptor strengths using large and diverse training data generated by first-principles interaction free energies

2019 ◽  
Vol 11 (1) ◽  
Author(s):  
Christoph A. Bauer ◽  
Gisbert Schneider ◽  
Andreas H. Göller
Keyword(s):  
Machine Learning ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Training Data ◽  
Free Energies ◽  
Hydrogen Bond Donor ◽  
Chemical Application ◽  
Hydrogen Bond Acceptor ◽  
Donor And Acceptor ◽  
Target Values

Abstract We present machine learning (ML) models for hydrogen bond acceptor (HBA) and hydrogen bond donor (HBD) strengths. Quantum chemical (QC) free energies in solution for 1:1 hydrogen-bonded complex formation to the reference molecules 4-fluorophenol and acetone serve as our target values. Our acceptor and donor databases are the largest on record with 4426 and 1036 data points, respectively. After scanning over radial atomic descriptors and ML methods, our final trained HBA and HBD ML models achieve RMSEs of 3.8 kJ mol−1 (acceptors), and 2.3 kJ mol−1 (donors) on experimental test sets, respectively. This performance is comparable with previous models that are trained on experimental hydrogen bonding free energies, indicating that molecular QC data can serve as substitute for experiment. The potential ramifications thereof could lead to a full replacement of wetlab chemistry for HBA/HBD strength determination by QC. As a possible chemical application of our ML models, we highlight our predicted HBA and HBD strengths as possible descriptors in two case studies on trends in intramolecular hydrogen bonding.

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