Cooperation and competition of hydrogen and halogen bonds in 2D self-assembled nanostructures based on bromine substituted coumarins

2019 ◽  
Vol 43 (44) ◽  
pp. 17182-17187 ◽  
Author(s):  
Bao Zha ◽  
Jinxing Li ◽  
Juntian Wu ◽  
Xinrui Miao ◽  
Min Zhang
Keyword(s):  
Coumarin Derivatives ◽  
Carbonyl Groups ◽  
Halogen Bonds ◽  
Cooperation And Competition ◽  
Self Assembled ◽  
Substituted Coumarins

Three coumarin derivatives (Co16, 6-Br-Co16 and 6,8-Br-Co16) with ester, ether, and carbonyl groups and different numbers of bromine substituents on the coumarin cores were synthesized.

scholarly journals Halogen Bonds Fabricate 2D Molecular Self-Assembled Nanostructures by Scanning Tunneling Microscopy

Crystals ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 1057
Author(s):  
Yi Wang ◽  
Xinrui Miao ◽  
Wenli Deng
Keyword(s):  
Scanning Tunneling Microscopy ◽  
Self Assembly ◽  
Density Functional ◽  
Deep Understanding ◽  
Halogen Bonding ◽  
The Self ◽  
Scanning Tunneling ◽  
Halogen Bonds ◽  
Tunneling Microscopy ◽  
Self Assembled

Halogen bonds are currently new noncovalent interactions due to their moderate strength and high directionality, which are widely investigated in crystal engineering. The study about supramolecular two-dimensional architectures on solid surfaces fabricated by halogen bonding has been performed recently. Scanning tunneling microscopy (STM) has the advantages of realizing in situ, real-time, and atomic-level characterization. Our group has carried out molecular self-assembly induced by halogen bonds at the liquid–solid interface for about ten years. In this review, we mainly describe the concept and history of halogen bonding and the progress in the self-assembly of halogen-based organic molecules at the liquid/graphite interface in our laboratory. Our focus is mainly on (1) the effect of position, number, and type of halogen substituent on the formation of nanostructures; (2) the competition and cooperation of the halogen bond and the hydrogen bond; (3) solution concentration and solvent effects on the molecular assembly; and (4) a deep understanding of the self-assembled mechanism by density functional theory (DFT) calculations.

scholarly journals Evaluation of Some Salicylaldehyde-derived Baylis-Hillman Adducts and Coumarin Derivatives as Potential Antisickling Compounds

2018 ◽  
Vol 3 (1) ◽  
pp. 35-42
Author(s):  
Temitope O. Olomola ◽  
Tawakalit O. Kelani ◽  
Mojisola C. Cyril-Olutayo ◽  
Joseph M. Agbedahunsi
Keyword(s):  
Red Blood Cells ◽  
Inhibitory Activity ◽  
Blood Cells ◽  
Hydroxybenzoic Acid ◽  
Coumarin Derivatives ◽  
Sickle Cells ◽  
Rate Of Polymerization ◽  
Dose Dependent ◽  
Substituted Coumarins

AbstractSome salicylaldehyde-derived Baylis-Hillman adducts and 3-(chloromethyl)coumarins have been synthesised and evaluated in vitro for their antisickling activities. The compounds were screened for inhibitory and reversal activity against mutated haemoglobin (HbSS) in red blood cells at four different concentrations (4 mg/mL, 2 mg/mL, 1 mg/mL and 0.5 mg/mL) as a measure of their antisickling potentials. Among the synthesized compounds, 6-chloro-3-(chloromethyl)coumarin 4d showed the highest inhibitory activity (83.75±1.90%), followed by 6-chlorocoumarin-3-methylsulfinic acid 5d (80.90 ±0.91%) and the least was tert-butyl-3-hydroxy- 3-(2-hydroxyphenyl)-2-methylenepropanoate 3a (33.33±1.86%). The results obtained from the reversal antisickling experiment showed that the percentage of sickle cells able to revert to the normal biconcave shape was dose dependent. Compound 5d had the highest reversal activity (66.49±1.39%) followed by 6-bromo-3- (chloromethyl)coumarin 4c (59.66±2.95) and 4d (55.50±1.95%) at 4 mg/mL. Compound 4c had higher reversal activity than the standard p-hydroxybenzoic acid at 2 mg/mL, 1 mg/mL and at 0.5 mg/mL. The 3-substituted coumarins 4a-d, and 5d had higher inhibitory antisickling activities than their Baylis-Hillman precursors 3a-d. Effect of 4a-d and 5d on the rate of polymerization of sickle cell heamoglobin was further studied spectrophotomerically using hemolysate of HbSS. The considerable inhibitory and reversal activities of these compounds make them good candidates for further antisickling studies.

Halogen bonding versus hydrogen bonding induced 2D self-assembled nanostructures at the liquid–solid interface revealed by STM

2017 ◽  
Vol 19 (4) ◽  
pp. 3143-3150 ◽  
Author(s):  
Yican Wu ◽  
Jinxing Li ◽  
Yinlun Yuan ◽  
Meiqiu Dong ◽  
Bao Zha ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Octanoic Acid ◽  
Halogen Bonding ◽  
Halogen Bonds ◽  
Solid Interface ◽  
Self Assembled

5-BHBA mainly forms CO⋯Br⋯H–C halogen bonds in 1-octanoic acid and forms –COOH⋯HOOC– hydrogen bonds in n-hexadecane.

scholarly journals Superhydrophilic Coating of Pine Wood by Plasma Functionalization of Self-Assembled Polystyrene Spheres

2020 ◽  
Author(s):  
Sebastian Dahle ◽  
John Meuthen ◽  
René Gustus ◽  
Alexandra Prowald ◽  
Wolfgang Viöl ◽  
...  
Keyword(s):  
Dip Coating ◽  
Particle Sizes ◽  
Carbonyl Groups ◽  
Wood Substrate ◽  
Polystyrene Spheres ◽  
Pine Wood ◽  
Self Assembling ◽  
Monodisperse Polystyrene ◽  
Self Assembled ◽  
Plasma Functionalization

Self-assembling films typically used for colloidal lithography have been applied to pine wood substrates to change the surface wettability. Therefore, monodisperse polystyrene (PS) spheres have been deposited onto a rough pine wood substrate via dip coating. The resulting PS sphere film resembled a polycrystalline FCC-like structure with typical domain sizes of 5 – 15 single spheres. This self-assembled coating was further functionalized via an O2 plasma. This plasma treatment strongly influenced the particle sizes in the outermost layer, and hydroxyl as well as carbonyl groups were introduced to the PS spheres’ surfaces, thus generating a superhydrophilic behaviour.

scholarly journals A Convergent Approach for the Synthesis of New Pyrazolyl Bipyridinyl Substituted Coumarin Derivatives as Antimicrobials

2014 ◽  
Vol 40 ◽  
pp. 1-16 ◽  
Author(s):  
Varun G. Bhila ◽  
Yogita L. Chovatiya ◽  
Chirag V. Patel ◽  
Rakesh R. Giri ◽  
Dinkar I. Brahmbhatt
Keyword(s):  
Antimicrobial Activity ◽  
Coumarin Derivatives ◽  
Mass Spectral Analysis ◽  
Mass Spectral ◽  
H Nmr ◽  
Convergent Approach ◽  
C Nmr ◽  
Substituted Coumarins

Some new 3-[3-(1-phenyl-3-aryl-1H-pyrazol-4-yl) acryloyl] coumarins 3a-f were synthesized (coumarin chalcones) by the condensation of various 3-acetyl coumarins 1 and appropriate 1-phenyl-3-aryl-1H-pyrazole-4-carbaldehyde 2. These coumarin chalcones 3a-f were then employed for the synthesis of pyrazolyl bipyridinyl substituted coumarins 7a-f, 8a-f, and 9a-f under Krohnke’s reaction condition. The characterization of all the synthesized compounds was carried out by elemental analysis, IR, 1H-NMR, 13C-NMR, DEPT-135 and mass spectral analysis. In addition to that, in vitro antimicrobial competency of the title compounds was assessed against selected pathogens. Compounds 3b, 3e, 7b, 8b, 8c and 9b exhibited excellent antimicrobial activity and said to be the most proficient members of the series.

Design, Synthesis and Evaluation of Antioxidant Activity of Some Coumarin Derivatives

2019 ◽  
Vol 4 (3) ◽  
pp. 138-143
Author(s):  
R.D. Ukirde ◽  
R.B. Patil ◽  
S.D. Sawant
Keyword(s):  
Antioxidant Activity ◽  
Heterocyclic Compounds ◽  
Coumarin Derivatives ◽  
Phosphoryl Chloride ◽  
Anticancer Activities ◽  
Design Synthesis ◽  
Derivatives Of ◽  
Substituted Coumarins ◽  
In Vitro Antioxidant Activity

Coumarin derivatives are an important class of heterocyclic compounds, specifically 4-amino substituted coumarins with antioxidant, anticancer activities. The above observations prompted us to synthesize new coumarins with various substitutions. The starting material 4-chloro-2H-chromen-2-one was synthesized by refluxing a mixture of 4-hydroxy-2H-chromen-2-one in phosphoryl chloride. The 4-substituted amine derivatives of coumarin were synthesized by refluxing 4-chloro-2H-chromen-2- one with 4-substituted amines and anhydrous K2CO3 and methanol. All the eleven 4-substituted amine derivatives of coumarin were synthesized by replacing chloro group with different amines. These coumarin derivatives were evaluated for in vitro antioxidant activity using quercetin as standard.

scholarly journals Supramolecular self-assembled network formation containing N⋯Br halogen bonds in physisorbed overlayers

2014 ◽  
Vol 16 (36) ◽  
pp. 19608-19617 ◽  
Author(s):  
Adam Y. Brewer ◽  
Marco Sacchi ◽  
Julia E. Parker ◽  
Chris L. Truscott ◽  
Stephen J. Jenkins ◽  
...  
Keyword(s):  
Network Formation ◽  
Halogen Bonds ◽  
Self Assembled ◽  
First Time

The formation of a halogen bonded self-assembled co-crystal physisorbed monolayer containing N⋯Br interactions is reported for the first time.

Strongly fluorescent organogels and self-assembled nanostructures from pyrene coupled coumarin derivatives: application in cell imaging

2015 ◽  
Vol 3 (28) ◽  
pp. 5690-5701 ◽  
Author(s):  
Krishnamoorthy Lalitha ◽  
Subbiah Nagarajan
Keyword(s):  
Fluorescence Imaging ◽  
Self Assembly ◽  
Cell Imaging ◽  
Assembly Process ◽  
Coumarin Derivatives ◽  
Facile Synthesis ◽  
Self Assembled

The present work reports facile synthesis of pyrene coupled coumarin derivatives which could form self-assembled molecular gel and nano-flakes. The nanomaterials obtained via a self-assembly process could be potentially used in fluorescence imaging applications.

Metal- and photocatalyst-free visible-light-promoted regioselective selenylation of coumarin derivatives via oxidation-induced C–H functionalization

2018 ◽  
Vol 5 (20) ◽  
pp. 2974-2979 ◽  
Author(s):  
Daoshan Yang ◽  
Guoqing Li ◽  
Chengyu Xing ◽  
Wenwen Cui ◽  
Kexin Li ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Coumarin Derivatives ◽  
Substituted Coumarins

A visible-light-promoted approach for the regioselective selenylation of 4-amino substituted coumarins has been initially realized under metal- and photocatalyst-free conditions at room temperature.

Halogen bonds as stabilizing interactions in a chiral self-assembled molecular monolayer

2011 ◽  
Vol 47 (33) ◽  
pp. 9453 ◽  
Author(s):  
Rico Gutzler ◽  
Oleksandr Ivasenko ◽  
Chaoying Fu ◽  
Jaclyn L. Brusso ◽  
Federico Rosei ◽  
...  
Keyword(s):  
Halogen Bonds ◽  
Self Assembled
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