Hydrogen-bond self-assembly of DNA-base analogues — Experimental results

2009 ◽  
Vol 87 (5) ◽  
pp. 627-639 ◽  
Author(s):  
Felaniaina Rakotondradany ◽  
Hanadi Sleiman ◽  
M. A. Whitehead
Keyword(s):  
Hydrogen Bond ◽  
Self Assembly ◽  
Cyanuric Acid ◽  
Experimental Studies ◽  
Acid Complex ◽  
Hybridization Probes ◽  
Dna Strands ◽  
Artificial Dna ◽  
Self Association ◽  
Hydrogen Bonded

A novel biomimetic DNA analogue with fluorescence has been synthesized to generate functional supramolecular architectures. Experimental studies show that triaminopyrimidine nucleoside (2) undergoes a sterically controlled self-assembly into hydrogen-bonded linear tapes and hexameric rosettes. Self-association of the hydrogen-bonded triaminopyrimidine–cyanuric acid complex into elongated, rodlike nanostructures was shown by dynamic light scattering and transmission electron microscopy, suggesting hierarchical formation of higher-order, π-stacked assemblies. The hydrogen-bond self-assembly of the DNA analogue decreased the fluorescence of the nucleosides. This guest-induced fluorescence quenching can be used to develop DNA-hybridization probes. MM+ molecular modelling and semi-empirical molecular orbital PM3 calculations (1) predicted the incorporation of triaminopyrimidine nucleoside into new types of artificial DNA strands and triplex formation with natural, complementary DNA strands containing thymine (1).

Surface self-assembly of the cyanuric acid–melamine hydrogen bonded network

2006 ◽  
pp. 538-540 ◽  
Author(s):  
Luís M. A. Perdigão ◽  
Neil R. Champness ◽  
Peter H. Beton
Keyword(s):  
Self Assembly ◽  
Cyanuric Acid ◽  
Hydrogen Bonded

scholarly journals In situ modification of nanostructure configuration through the manipulation of hydrogen bonded amphiphile self-association

Soft Matter ◽  
2016 ◽  
Vol 12 (18) ◽  
pp. 4221-4228 ◽  
Author(s):  
Jennifer R. Hiscock ◽  
Gianluca P. Bustone ◽  
Ben Wilson ◽  
Kate E. Belsey ◽  
Laura R. Blackholly
Keyword(s):  
Hydrogen Bond ◽  
Nanostructure Formation ◽  
In Situ Modification ◽  
Self Association ◽  
Hydrogen Bonded

Previously overlooked simple amphiphiles show an exciting capacity for complex hydrogen bond mediated self-association and diverse nanostructure formation.

scholarly journals ‘Frustrated’ hydrogen bond mediated amphiphile self-assembly – a solid state study

CrystEngComm ◽  
2016 ◽  
Vol 18 (37) ◽  
pp. 7021-7028 ◽  
Author(s):  
Laura R. Blackholly ◽  
Helena J. Shepherd ◽  
Jennifer R. Hiscock
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Self Assembly ◽  
Hydrogen Bond Donor ◽  
System P ◽  
State Study ◽  
Counter Cation ◽  
Self Assembled ◽  
Hydrogen Bonded

The effects of hydrogen bond donor acidity and counter cation within a ‘frustrated’ self-assembled, hydrogen bonded system.

N-Tosyl-L-proline benzene hemisolvate: a rare example of a hydrogen-bonded carboxylic acid dimer with symmetrically disordered H atoms

2019 ◽  
Vol 75 (9) ◽  
pp. 1228-1233
Author(s):  
Joanna Wojnarska ◽  
Katarzyna Ostrowska ◽  
Marlena Gryl ◽  
Katarzyna Marta Stadnicka
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Self Assembly ◽  
Acid Group ◽  
Benzene Molecule ◽  
Noncovalent Interaction ◽  
Hydrogen Bond Donor ◽  
Donor And Acceptor ◽  
Carboxylic Acid Dimer ◽  
Hydrogen Bonded

The carboxylic acid group is an example of a functional group which possess a good hydrogen-bond donor (–OH) and acceptor (C=O). For this reason, carboxylic acids have a tendency to self-assembly by the formation of hydrogen bonds between the donor and acceptor sites. We present here the crystal structure of N-tosyl-L-proline (TPOH) benzene hemisolvate {systematic name: (2S)-1-[(4-methylbenzene)sulfonyl]pyrrolidine-2-carboxylic acid benzene hemisolvate}, C12H15NO4S·0.5C6H6, (I), in which a cyclic R 2 2(8) hydrogen-bonded carboxylic acid dimer with a strong O—(1 \over 2H)...(1 \over 2H)—O hydrogen bond is observed. The compound was characterized by single-crystal X-ray diffraction and NMR spectroscopy, and crystallizes in the space group I2 with half a benzene molecule and one TPOH molecule in the asymmetric unit. The H atom of the carboxyl OH group is disordered over a twofold axis. An analysis of the intermolecular interactions using the noncovalent interaction (NCI) index showed that the TPOH molecules form dimers due to the strong O—(1 \over 2H)...(1 \over 2H)—O hydrogen bond, while the packing of the benzene solvent molecules is governed by weak dispersive interactions. A search of the Cambridge Structural Database revealed that the disordered dimeric motif observed in (I) was found previously only in six crystal structures.

Hydrogen bonded interactions of methanol and water with purines and pyrimidines

1983 ◽  
Vol 61 (12) ◽  
pp. 2695-2698 ◽  
Author(s):  
J. N. Spencer ◽  
S. W. Barton ◽  
K. A. Smith ◽  
W. S. Wolbach ◽  
J. F. Powell ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Bond Formation ◽  
Intermolecular Hydrogen Bond ◽  
Solvation Shell ◽  
The Self ◽  
Hydrogen Bond Formation ◽  
Interaction Site ◽  
Self Association ◽  
Purines And Pyrimidines ◽  
Hydrogen Bonded

The solvation of benzimidazole, 4-azabenzimidazole, purine, adenine, uracil, thymine, and cytosine in water and methanol was determined by a combination of calorimetric and spectral analysis. Specific enthalpies have been assigned to each interaction site in the first solvation shell. Calculations, based on the enthalpies of hydrogen bond formation with water, and estimates for intermolecular hydrogen bond enthalpies, show that the self-association of purine and adenine in water through hydrogen bonded interactions is enthalpically possible.

Evaporative self-assembly of binary mixture of soft colloids

2021 ◽  
Author(s):  
Merin Jose ◽  
Muraleedharapai Mayarani ◽  
Madivala G Basavaraj ◽  
Dillip Kumar Satapathy
Keyword(s):  
Binary Mixture ◽  
Self Assembly ◽  
Sessile Drop ◽  
Experimental Studies ◽  
The Self ◽  
Soft Colloids

We report experimental studies on the self-assembly and degree of ordering of binary mixture of soft colloids in the monolayer deposits obtained by controlled evaporation. A sessile drop containing soft...

scholarly journals Synthesis of microporous hydrogen-bonded supramolecular organic frameworks through guanosine self-assembly

2021 ◽  
pp. 100519
Author(s):  
Ying He ◽  
Yanbin Zhang ◽  
Mengjia Liu ◽  
Kai Zhao ◽  
Chuan Shan ◽  
...  
Keyword(s):  
Self Assembly ◽  
Hydrogen Bonded

scholarly journals Taming nitroformate through encapsulation with nitrogen-rich hydrogen-bonded organic frameworks

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Jichuan Zhang ◽  
Yongan Feng ◽  
Richard J. Staples ◽  
Jiaheng Zhang ◽  
Jean’ne M. Shreeve
Keyword(s):  
Thermal Stability ◽  
Hydrogen Bonds ◽  
Self Assembly ◽  
Energetic Materials ◽  
Decomposition Temperature ◽  
High Oxygen Content ◽  
The Poor ◽  
Simple Preparation ◽  
First Time ◽  
Hydrogen Bonded

AbstractOwing to its simple preparation and high oxygen content, nitroformate [−C(NO2)3, NF] is an extremely attractive oxidant component for propellants and explosives. However, the poor thermostability of NF-based derivatives has been an unconquerable barrier for more than 150 years, thus hindering its application. In this study, the first example of a nitrogen-rich hydrogen-bonded organic framework (HOF-NF) is designed and constructed through self-assembly in energetic materials, in which NF anions are trapped in pores of the resulting framework via the dual force of ionic and hydrogen bonds from the strengthened framework. These factors lead to the decomposition temperature of the resulting HOF-NF moiety being 200 °C, which exceeds the challenge of thermal stability over 180 °C for the first time among NF-based compounds. A large number of NF-based compounds with high stabilities and excellent properties can be designed and synthesized on the basis of this work.

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