Halogen-bond driven self-assembly of triangular macrocycles

2018 ◽  
Vol 42 (13) ◽  
pp. 10467-10471 ◽  
Author(s):  
Patrick M. J. Szell ◽  
Antti Siiskonen ◽  
Luca Catalano ◽  
Gabriella Cavallo ◽  
Giancarlo Terraneo ◽  
...  
Keyword(s):  
Self Assembly ◽  
Halogen Bond ◽  
The Self ◽  
Halogen Bonds ◽  
Methyl Imidazole

Halogen bonds drive the self-assembly of 2-iodoethynylpyridine and 2- iodoethynyl-1-methyl-imidazole into discrete supramolecular triangles.

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.

Anion Templated Crystal Engineering of Halogen Bonding Tripodal Tris(halopyridinium) Compounds

2020 ◽  
Author(s):  
Emer Foyle ◽  
Nicholas White
Keyword(s):  
Crystal Engineering ◽  
Self Assembly ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Halogen Bonds ◽  
X Ray ◽  
X Ray Crystallography ◽  
H Nmr ◽  
Structural Database ◽  
Van Der Waals Radii

<div>In this work four new tripodal tris(halopyridinium) receptors containing potentially halogen</div><div>bonding groups were prepared. The ability of the receptors to bind anions in competitive</div><div>CD<sub>3</sub>CN/d<sub>6</sub>-DMSO was studied using <sup>1</sup>H NMR titration experiments, which revealed that the</div><div>receptors bind chloride anions more strongly than more basic acetate or other halide ions.</div><div>The solid state self–assembly of the tripodal receptors with halide anions was investigated by</div><div>X-ray crystallography. The nature of the structures was dependent on the choice of halide</div><div>anion, as well as the crystallisation solvent. Halogen bond lengths as short as 80% of the sum</div><div>of the van der Waals radii were observed, which is shorter than any halogen bonds involving</div><div>halopyridinium receptors in the Cambridge Structural Database.</div>

Anion Templated Crystal Engineering of Halogen Bonding Tripodal Tris(halopyridinium) Compounds

2020 ◽  
Author(s):  
Emer Foyle ◽  
Nicholas White
Keyword(s):  
Crystal Engineering ◽  
Self Assembly ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Halogen Bonds ◽  
X Ray ◽  
X Ray Crystallography ◽  
H Nmr ◽  
Structural Database ◽  
Van Der Waals Radii

<div>In this work four new tripodal tris(halopyridinium) receptors containing potentially halogen</div><div>bonding groups were prepared. The ability of the receptors to bind anions in competitive</div><div>CD<sub>3</sub>CN/d<sub>6</sub>-DMSO was studied using <sup>1</sup>H NMR titration experiments, which revealed that the</div><div>receptors bind chloride anions more strongly than more basic acetate or other halide ions.</div><div>The solid state self–assembly of the tripodal receptors with halide anions was investigated by</div><div>X-ray crystallography. The nature of the structures was dependent on the choice of halide</div><div>anion, as well as the crystallisation solvent. Halogen bond lengths as short as 80% of the sum</div><div>of the van der Waals radii were observed, which is shorter than any halogen bonds involving</div><div>halopyridinium receptors in the Cambridge Structural Database.</div>

scholarly journals Crystallographic insights into the structural aspects of thioctic acid based halogen-bond donor for the functionalization of gold nanoparticles

2017 ◽  
Vol 73 (2) ◽  
pp. 240-246 ◽  
Author(s):  
Kavitha Buntara Sanjeeva ◽  
Ilaria Tirotta ◽  
Vijith Kumar ◽  
Francesca Baldelli Bombelli ◽  
Giancarlo Terraneo ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Gold Nanoparticles ◽  
Self Assembly ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Thioctic Acid ◽  
Halogen Bonds ◽  
Donor Ligand ◽  
Structural Aspects

The synthesis and self-assembly capabilities of a new halogen-bond donor ligand, 2,3,5,6-tetrafluoro-4-iodophenyl 5-(1,2-dithiolan-3-yl)pentanoate (1), are reported. The crystal structure of ligand (1) and the formation of a cocrystal with 1,2-di(4-pyridyl)ethylene, (1)·(2), both show halogen bonds involving the 4-iodotetrafluorobenzene moiety. Ligand (1), being a self-complementary unit, forms an infinite halogen-bonded chain driven by the S...I synthon, while the cocrystal (1)·(2) self-assembles into a discrete trimeric entity driven by the N...I synthon. Ligand (1) was also successfully used to functionalize the surface of gold nanoparticles, AuNP-(1). Experiments on the dispersibility profile of AuNP-(1) demonstrated the potential of halogen bonding in facilitating the dispersion of modified NPs with halogen-bond donors in pyridine.

Halogen bonding controlled 2D self-assembled polymorphism of regioisomeric thienophenanthrene derivatives by coadsorption

2021 ◽  
Author(s):  
Peng Pang ◽  
Yi Wang ◽  
Xinrui Miao ◽  
Bang Li ◽  
Wenli Deng
Keyword(s):  
Hydrogen Bonding ◽  
Formation Mechanism ◽  
Self Assembly ◽  
Halogen Bond ◽  
Bond Formation ◽  
Halogen Bonding ◽  
Supramolecular Assemblies ◽  
The Self ◽  
Self Assembled

Deeply understanding the halogen-bond formation mechanism in surface-supported supramolecular assemblies is under explored compared with the existing knowledge of hydrogen bonding. Here we report the self-assembly of regioisomeric bromine substituted...

A family of powerful halogen-bond donors: A structural and theoretical analysis of triply activated 3-iodo-1-phenylprop-2-yn-1-ones

CrystEngComm ◽  
2022 ◽  
Author(s):  
Vinu V Panikkattu ◽  
Abhijeet Shekhar Sinha ◽  
Christer Aakeröy
Keyword(s):  
Theoretical Analysis ◽  
Self Assembly ◽  
Halogen Bond ◽  
Functional Materials ◽  
Halogen Bonds ◽  
New Class

Strong halogen bonds can provide a foundation for reliable supramolecular strategies for effective self-assembly and design of functional materials. A new class of halogen-bond donors have been developed using structural...

Crystalline assemblies of porphyrins with mixed bromophenyl and pyridyl meso-substituents and manifestation of supramolecular chirality induced by inter-porphyrin Br⋯N halogen bonds

2011 ◽  
Vol 15 (11n12) ◽  
pp. 1250-1257 ◽  
Author(s):  
Hatem M. Titi ◽  
Anirban Karmakar ◽  
Israel Goldberg
Keyword(s):  
Self Assembly ◽  
Halogen Bond ◽  
Supramolecular Assembly ◽  
Halogen Bonding ◽  
Building Blocks ◽  
Zinc Ion ◽  
Halogen Bonds ◽  
X Ray Diffraction ◽  
Supramolecular Chirality ◽  
Porphyrin Core

Four new crystalline solids based on the zinc-5,15-bis(4′-bromophenyl)-10,20- bis(4′-pyridyl)porphyrin ( Zn –DBDPyP) and zinc/copper-5,10,15-tris(4′-bromophenyl)-20-(4′-pyridyl)-porphyrin ( Zn/Cu –TBMPyP) platforms as building blocks, have been prepared and structurally analyzed by X-ray diffraction in order to examine whether the Br⋯N halogen bond can be effective in directing the supramolecular assembly of this functionalized porphyrins, in a similar way observed earlier for their iodophenyl-substituted analogs. The zinc ion in the porphyrin core was protected by an external ligand (pyridyl or methanol) to prevent its possible coordination to the pyridyl-porphyrin substituents. Neither the bis-pyridyl Zn (py)–DBDPyP scaffold nor the Zn(MeOH)/Cu –TBMPyP exhibited inter-porphyrin halogen bonding in their corresponding crystals. Only the layered self-assembly of the Zn (py)–TBMPyP building block was found to be uniquely directed by Br⋯N halogen bonds, as well as by Br⋯Br and Br⋯π interactions. This observation supports our notion that asymmetric functionalization of the tetraarylporphyrin scaffold, combined with directional interporphyrin interactions (as halogen bonding), represent a promising approach to supramolecular chirality.

scholarly journals Surface-controlled reversal of the selectivity of halogen bonds

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Jalmar Tschakert ◽  
Qigang Zhong ◽  
Daniel Martin-Jimenez ◽  
Jaime Carracedo-Cosme ◽  
Carlos Romero-Muñiz ◽  
...  
Keyword(s):  
Gas Phase ◽  
Self Assembly ◽  
Organic Molecules ◽  
Halogen Bond ◽  
Control Parameters ◽  
Halogen Bonds ◽  
Molecular Assemblies ◽  
Molecular Charge ◽  
Different Types ◽  
Bond Strengths

Abstract Intermolecular halogen bonds are ideally suited for designing new molecular assemblies because of their strong directionality and the possibility of tuning the interactions by using different types of halogens or molecular moieties. Due to these unique properties of the halogen bonds, numerous areas of application have recently been identified and are still emerging. Here, we present an approach for controlling the 2D self-assembly process of organic molecules by adsorption to reactive vs. inert metal surfaces. Therewith, the order of halogen bond strengths that is known from gas phase or liquids can be reversed. Our approach relies on adjusting the molecular charge distribution, i.e., the σ-hole, by molecule-substrate interactions. The polarizability of the halogen and the reactiveness of the metal substrate are serving as control parameters. Our results establish the surface as a control knob for tuning molecular assemblies by reversing the selectivity of bonding sites, which is interesting for future applications.

The Nature of Rapidly Extracted Phycocyanin from the Blue-Green Alga Plectonema Boryanum

1971 ◽  
Vol 29 ◽  
pp. 366-367
Author(s):  
M. Kessel ◽  
R. MacColl
Keyword(s):  
Self Assembly ◽  
Analytical Ultracentrifugation ◽  
Uranyl Acetate ◽  
The Self ◽  
Major Protein ◽  
Subunit Structure ◽  
Blue Green Alga ◽  
Thin Sections ◽  
Blue Green Algae ◽  
Cacodylate Buffer

The major protein of the blue-green algae is the biliprotein, C-phycocyanin (Amax = 620 nm), which is presumed to exist in the cell in the form of distinct aggregates called phycobilisomes. The self-assembly of C-phycocyanin from monomer to hexamer has been extensively studied, but the proposed next step in the assembly of a phycobilisome, the formation of 19s subunits, is completely unknown. We have used electron microscopy and analytical ultracentrifugation in combination with a method for rapid and gentle extraction of phycocyanin to study its subunit structure and assembly.To establish the existence of phycobilisomes, cells of P. boryanum in the log phase of growth, growing at a light intensity of 200 foot candles, were fixed in 2% glutaraldehyde in 0.1M cacodylate buffer, pH 7.0, for 3 hours at 4°C. The cells were post-fixed in 1% OsO4 in the same buffer overnight. Material was stained for 1 hour in uranyl acetate (1%), dehydrated and embedded in araldite and examined in thin sections.

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