Two‐Dimensional Supramolecular Chemistry on Surfaces

2021 ◽  
pp. 1-8
Author(s):  
Neil R. Champness
Keyword(s):  
Supramolecular Chemistry ◽  
Two Dimensional

Supramolecular chemistry of amine–phenol adducts; novel three-dimensional framework structures in adducts of bis(2-aminoethyl)amine with 4,4′-sulfonyldiphenol, 1,1,1-tris(4-hydroxyphenyl)ethane and 3,5-dihydroxybenzoic acid, and in the methanol-solvated adduct of tris(2-aminoethyl)amine with 4,4′-biphenol

2000 ◽  
Vol 56 (1) ◽  
pp. 68-84 ◽  
Author(s):  
Christopher Glidewell ◽  
George Ferguson ◽  
Richard M. Gregson ◽  
Charles F. Campana
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Three Dimensional ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Dihydroxybenzoic Acid ◽  
Nearest Neighbours ◽  
Molecular Components

Bis(2-aminoethyl)amine–4,4′-sulfonyldiphenol (1/3) (1) (orthorhombic Pccn with Z′ = 0.5) is a salt, [HN(CH2CH2NH3)2]2+.[O2S(C6H4O)2]2−.[O2S(C6H4OH)2]2, containing both dianionic and neutral bis-phenol units. The neutral and anionic bis-phenol units are linked by strong O—H...O− hydrogen bonds to form ladders built from R{_4}{^4}(48) rings: each ladder is interwoven with its two nearest neighbours to form a continuous two-dimensional sheet. The amine cations play two roles: they link each ladder to its two next-nearest neighbours by means of N—H...O hydrogen bonds and they also link each sheet to the two neighbouring sheets, again via N—H...O hydrogen bonds, thus generating a three-dimensional framework. Bis(2-aminoethyl)amine–1,1,1-tris(4-hydroxyphenyl)ethane–methanol (1/4/1) (2) (triclinic P1¯ with Z′ = 0.5) consists entirely of neutral fragments. The tris-phenol units are linked by O—H...O hydrogen bonds into molecular ladders built from R{_4}{^4}(48) rings: these ladders are linked by the amine units, firstly into sheets and thence into a three-dimensional framework. Bis(2-aminoethyl)amine–3,5-dihydroxybenzoic acid (1/2) (3) (monoclinic P21/c with Z′ = 1) is a salt [HN(CH2CH2NH3)2]2+.[{(HO)2C6H3COO}−]2. The 3,5-dihydroxybenzoate anions are linked by O—H...O hydrogen bonds into interwoven and cross-connected (001) sheets linked by further O—H...O hydrogen bonds into a three-dimensional framework. The (001) sheets are further linked by ladders formed from both cations and anions. Tris(2-aminoethyl)amine–4,4′-biphenol–methanol (1/3/1), (4) (monoclinic P21), is a salt [{(H2NCH2CH2)2N(CH2CH2NH3)}+]2.[OC6H4C6H4O]2−.[HOC6H4C6H4OH]5.[MeOH]2, with Z′ = 1. The asymmetric unit, containing ten independent molecular components, can be regarded as a supermolecule held together by a total of 13 independent hydrogen bonds, of O—H...O, O—H...N and N—H...O types. The supermolecules are linked by O—H...O and N—H...O hydrogen bonds into two-dimensional sheets, generated by translation; further N—H...O hydrogen bonds around the 21 screw axes link neighbouring sheets together into a three-dimensional framework.

Oligosiloxanediols as building blocks for supramolecular chemistry: hydrogen-bonded adducts with amines form supramolecular structures in zero, one and two dimensions

2000 ◽  
Vol 56 (2) ◽  
pp. 273-286 ◽  
Author(s):  
Brian O'Leary ◽  
Trevor R. Spalding ◽  
George Ferguson ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Building Blocks ◽  
Two Dimensions ◽  
Supramolecular Structures ◽  
Structural Motif ◽  
Two Dimensional ◽  
The Third ◽  
A Chain ◽  
Hydrogen Bonded

The structure of 1,1,3,3,5,5-hexaphenyltrisiloxane-1,5-diol–pyrazine (4/1), (C36H32O4Si3)4·C4H4N2 (1), contains finite centrosymmetric aggregates; the diol units form dimers, by means of O—H...O hydrogen bonds, and pairs of such dimers are linked to the pyrazine by means of O—H...N hydrogen bonds. In 1,1,3,3,5,5-hexaphenyltrisiloxane-1,5-diol–pyridine (2/3), (C36H32O4Si3)2·(C5H5N)3 (2), the diol units are linked into centrosymmetric pairs by means of disordered O—H...O hydrogen bonds: two of the three pyridine molecules are linked to the diol dimer by means of ordered O—H...N hydrogen bonds, while the third pyridine unit, which is disordered across a centre of inversion, links the diol dimers into a C 3 3(9) chain by means of O—H...N and C—H...O hydrogen bonds. In 1,1,3,3-tetraphenyldisiloxane-1,3-diol–hexamethylenetetramine (1/1), (C24H22O3Si2)·C6H12N4 (3), the diol acts as a double donor and the hexamethylenetetramine acts as a double acceptor in ordered O—H...N hydrogen bonds and the structure consists of C 2 2(10) chains of alternating diol and amine units. In 1,1,3,3-tetraphenyldisiloxane-1,3-diol–2,2′-bipyridyl (1/1), C24H22O3Si2·C10H8N2 (4), there are two independent diol molecules, both lying across centres of inversion and therefore both containing linear Si—O—Si groups: each diol acts as a double donor of hydrogen bonds and the unique 2,2′-bipyridyl molecule acts as a double acceptor, thus forming C 2 2(11) chains of alternating diol and amine units. The structural motif in 1,1,3,3-tetraphenyldisiloxane-1,3-diol–pyrazine (2/1), (C24H22O3Si2)2·C4H4N2 (5), is a chain-of-rings: pairs of diol molecules are linked by O—H...O hydrogen bonds into centrosymmetric R 2 2(12) dimers and these dimers are linked into C 2 2(13) chains by means of O—H...N hydrogen bonds to the pyrazine units. 1,1,3,3-Tetraphenyldisiloxane-1,3-diol–pyridine (1/1), C24H22O3Si2·C5H5N (6), and 1,1,3,3-tetraphenyldisiloxane-1,3-diol–pyrimidine (1/1), C24H22O3Si2·C4H4N2 (7), are isomorphous: in each compound the amine unit is disordered across a centre of inversion. The diol molecules form C(6) chains, by means of disordered O—H...O hydrogen bonds, and these chains are linked into two-dimensional nets built from R 6 6(26) rings, by a combination of O—H...N and C—H...O hydrogen bonds.

Two-dimensional supramolecular chemistry on surfaces

2011 ◽  
Vol 2 (8) ◽  
pp. 1440 ◽  
Author(s):  
Anna G. Slater (née Phillips) ◽  
Peter H. Beton ◽  
Neil R. Champness
Keyword(s):  
Supramolecular Chemistry ◽  
Two Dimensional

[1-(Pyrazin-2-yl)ethylidene]hydrazine: a new multitopic ligand for the design of hybrid molecular frameworks

2018 ◽  
Vol 74 (4) ◽  
pp. 424-427
Author(s):  
Muhammad Arif Kassim ◽  
Ubaidullah H. M. Yassin ◽  
Ai Ling Tan ◽  
Anwar Usman ◽  
Malai Haniti S. A. Hamid
Keyword(s):  
Double Bond ◽  
Solid State ◽  
Supramolecular Chemistry ◽  
Title Compound ◽  
Antimicrobial Agents ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Two Dimensional ◽  
Compound C ◽  
Dimensional Network

Hydrazones and their derivatives are closely related to imine compounds and are potential antimicrobial agents. They have also found application in supramolecular chemistry as multitopic ligands to link multiple metal centres for the design of hybrid molecular frameworks. The molecule of the title compound, C6H8N4, consists of an imine linkage with an N—N bond length of 1.3540 (14) Å. This asymmetric compound is nearly planar and adopts an E configuration about the azomethine C=N double bond. In the solid state, there are two intermolecular N—H...N interactions that interconnect the molecules into a two-dimensional network. The three-dimensional arrangement of the crystal packing is further stabilized by intermolecular π–π interactions interconnecting the centroids of the heterocyclic rings.

Supramolecular Chemistry at the Liquid/Solid Interface a Scanning Tunneling Microscopy Approach

2007 ◽  
Vol 121-123 ◽  
pp. 369-372
Author(s):  
S. de Feyter ◽  
A. Miura ◽  
H. Uji-i ◽  
P. Jonkheijm ◽  
A.P.H.J. Schenning ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Scanning Tunneling Microscopy ◽  
Supramolecular Chemistry ◽  
Organic Molecules ◽  
Molecular Conformation ◽  
Scanning Tunneling ◽  
Conjugated Oligomers ◽  
Two Dimensional ◽  
Tunneling Microscopy ◽  
Solid Interface

With scanning tunneling microscopy (STM), the intramolecular conformational and intermolecular ordering aspects have been investigated of a variety of organic molecules physisorbed at the liquid-solid interface. By balancing the interplay between intramolecular and intermolecular interactions (hydrogen bonding), leading to control of the molecular conformation, foldamers were created which order into well-defined two-dimensional crystals. The nature of the hydrogen bonding groups in conjugated oligomers leads to the formation of infinite stacks and cyclic multimers, expressing the chiral nature of the molecules.

Tetraazaoctaphyrin — A biimidazole-containing expanded porphyrin

2006 ◽  
Vol 84 (10) ◽  
pp. 1218-1225 ◽  
Author(s):  
Jonathan L Sessler ◽  
Bobbi L Rubin ◽  
Marcin Stępień ◽  
Thomas Köhler ◽  
G Dan Pantos ◽  
...  
Keyword(s):  
Molecular Modeling ◽  
Supramolecular Chemistry ◽  
Spectroscopic Studies ◽  
Relative Energy ◽  
Two Dimensional ◽  
Asymmetric Structures ◽  
Expanded Porphyrins ◽  
Expanded Porphyrin

A series of expanded porphyrins, incorporating biimidazoles and bipyrroles within their macrocyclic framework, has been synthesized. Insights into the complex conformational characteristics of these ems were obtained from two-dimensional NMR spectroscopic studies. The relative energy values for the various asymmetric structures inferred from these analyses were compared using DFT molecular modeling calculations.Key words: macrocycles, expanded porphyrins, imidazoles, pyrroles, biimidazoles, supramolecular chemistry, heterocycles.

Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines

2003 ◽  
Vol 59 (2) ◽  
pp. 248-262 ◽  
Author(s):  
Katharine F. Bowes ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Water Molecules ◽  
Two Dimensional ◽  
Phosphonoacetic Acid ◽  
Space Group ◽  
Hydrated Salt ◽  
Hydrogen Bonded

The structures of seven salts formed by phosphonopropionic acid with organic diamines are reported; in these salts, the hydrogen-bonded substructures formed by the anions can be zero-, one- or two-dimensional, while the overall hydrogen-bonded supramolecular structures are three-dimensional. The 1:1 adduct, compound (1), formed between 1,2-bis(4′-pyridyl)ethene and phosphonopropionic acid is a salt, [{(C12H10N2)H2}2+]·[(C12H10N2)]·[(C3H6O5P)−]2, in which both diamine components lie across centres of inversion in space group P21/c. The anions form hydrogen-bonded head-to-head dimers, and these are linked by the two diamine units into sheets, which are themselves linked by C—H...O hydrogen bonds. With 2,2′-dipyridylamine the acid forms the hydrated salt [{(C10H9N3)H}+]·[(C3H6O5P)−]·H2O (2), in which all components are disordered with occupancy 0.5 in space group Fmm2. The anions form head-to-tail dimers, which are linked into sheets by the cations, and the sheets are linked into a three-dimensional framework by the water molecules. The piperazine salt [{(C4H10N2)H2}2+]·[(C3H5O5P)2−] (3) contains simple anion chains linked into a three-dimensional framework by the two independent cations, both of which are centrosymmetric. In the hydrated salt formed by N,N′-dimethylpiperazine, [{(MeNC4H8NMe)H2}2+]·[(C3H6O5P)−]2·(H2O)2 (4), head-to-tail anion chains combine with the water molecules to form a three-dimensional framework, which encloses voids that contain the cations. In the 4,4′-bipyridyl adduct [{(C10H8N2)H0.72}0.72+]·[{(H0.5O)3PCH2CH2COOH0.78}0.72−] (5), there is extensive disorder of the H atoms that are bonded to N and O atoms, and the anion chains are linked by the cations into sheets, which are themselves linked by C—H...O hydrogen bonds. In the 1:2 adduct formed with 1,2-bis(4′-pyridyl)ethane, [{(C12H12N2)H2}2+]·[(C3H6O5P)−]2 (6), where the cation lies across an inversion centre, the anions form molecular ladders. These ladders are linked into sheets by the cations, which are themselves linked by C—H...O hydrogen bonds. In the methanol-solvated salt formed with 2,6-dimethylpiperazine, [{(C6H14N2)H2}2+]·[(C3H6O5P)−]2· (CH4O)0.34 (7), the anions form sheets that are linked into a three-dimensional framework by the cations. The supramolecular structures are compared with those of analogous salts formed by phosphonoacetic acid.

scholarly journals Supramolecular tessellations by the exo-wall interactions of pagoda[4]arene

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xiao-Ni Han ◽  
Ying Han ◽  
Chuan-Feng Chen
Keyword(s):  
Charge Transfer ◽  
Supramolecular Chemistry ◽  
Building Block ◽  
Two Dimensional ◽  
Potential Applications ◽  
New Perspective ◽  
Rhombic Tiling ◽  
Tiling Patterns ◽  
Wall Charge ◽  
Wall Interactions

AbstractSupramolecular tessellation has gained increasing interest in supramolecular chemistry for its structural aesthetics and potential applications in optics, magnetics and catalysis. In this work, a new kind of supramolecular tessellations (STs) have been fabricated by the exo-wall interactions of pagoda[4]arene (P4). ST with rhombic tiling pattern was first constructed by P4 itself through favorable π···π interactions between anthracene units of adjacent P4. Notably, various highly ordered STs with different tiling patterns have been fabricated based on exo-wall charge transfer interactions between electron-rich P4 and electron-deficient guests including 1,4-dinitrobenzene, terephthalonitrile and tetrafluoroterephthalonitrile. Interestingly, solvent modulation and guest selection played a crucial role in controlling the molecular arrangements in the co-crystal superstructures. This work not only proves that P4 is an excellent macrocyclic building block for the fabrication of various STs, but also provides a new perspective and opportunity for the design and construction of supramolecular two-dimensional organic materials.

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