Cocrystals and Salts of 3,5-Bis(pyridinylmethylene)piperidin-4-one with Aromatic Poly-Carboxylates and Resorcinols: Influence of Stacking Interactions on Solid-State Luminescence Properties

2019 ◽  
Vol 72 (10) ◽  
pp. 742 ◽  
Author(s):  
Debarati Das ◽  
Kumar Biradha
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Benzoic Acid ◽  
The Other ◽  
Stacking Interactions ◽  
Unsaturated Ketones ◽  
Acid Acid ◽  
Ionic Hydrogen Bonds ◽  
State Luminescence ◽  
1D Chains

Two bis-pyridyl-substituted α,β-unsaturated ketones were shown to form complexes with carboxylic acids and resorcinol derivatives. The neutral acid–acid homosynthon was observed in only one complex out of the five acid-bis-pyridyl containing complexes studied here, while the –COO−⋯HOOC– synthon was found to be dominant as it was observed in four complexes. The carboxylates self-assembled to form discrete dimeric, anionic, 1D chains and also exhibited mixed ionic hydrogen bonds. On the other hand, resorcinol derivatives displayed O–H⋯N hydrogen bonding to form tetrameric aggregates of bis-pyridyl ketone molecules and respective co-formers, while 3,5-dihydroxy benzoic acid (DHBA) molecules formed 1D chains by clipping two molecules of ketones with three DHBA molecules. Such clipping by the resorcinol derivatives promoted continuous π–π stacking interactions. Consequently, these materials emitted at higher wavelengths compared with the parent bis-pyridyl-substituted α,β-unsaturated ketones.

Pentafluorophenyl Copper–Pyridine Complexes: Synthesis, Supramolecular Structures via Cuprophilic and π-Stacking Interactions, and Solid-State Luminescence

2011 ◽  
Vol 31 (4) ◽  
pp. 1546-1558 ◽  
Author(s):  
Ami Doshi ◽  
Anand Sundararaman ◽  
Krishnan Venkatasubbaiah ◽  
Lev N. Zakharov ◽  
Arnold L. Rheingold ◽  
...  
Keyword(s):  
Solid State ◽  
Supramolecular Structures ◽  
Stacking Interactions ◽  
Pyridine Complexes ◽  
Π Stacking ◽  
State Luminescence

scholarly journals The role of π–π stacking and hydrogen-bonding interactions in the assembly of a series of isostructural group IIB coordination compounds

2019 ◽  
Vol 75 (2) ◽  
pp. 178-188 ◽  
Author(s):  
Taraneh Hajiashrafi ◽  
Roghayeh Zekriazadeh ◽  
Keith J. Flanagan ◽  
Farnoush Kia ◽  
Antonio Bauzá ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Coordination Compounds ◽  
Spectroscopic Techniques ◽  
Stacking Interactions ◽  
X Ray Crystallography ◽  
Hydrogen Bonding Interactions ◽  
Π Stacking ◽  
Research Domain

The supramolecular chemistry of coordination compounds has become an important research domain of modern inorganic chemistry. Herein, six isostructural group IIB coordination compounds containing a 2-{[(2-methoxyphenyl)imino]methyl}phenol ligand, namely dichloridobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)zinc(II), [ZnCl2(C28H26N2O4)], 1, diiodidobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)zinc(II), [ZnI2(C28H26N2O4)], 2, dibromidobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)cadmium(II), [CdBr2(C28H26N2O4)], 3, diiodidobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)cadmium(II), [CdI2(C28H26N2O4)], 4, dichloridobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)mercury(II), [HgCl2(C28H26N2O4)], 5, and diiodidobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)mercury(II), [HgI2(C28H26N2O4)], 6, were synthesized and characterized by X-ray crystallography and spectroscopic techniques. All six compounds exhibit an infinite one-dimensional ladder in the solid state governed by the formation of hydrogen-bonding and π–π stacking interactions. The crystal structures of these compounds were studied using geometrical and Hirshfeld surface analyses. They have also been studied using M06-2X/def2-TZVP calculations and Bader's theory of `atoms in molecules'. The energies associated with the interactions, including the contribution of the different forces, have been evaluated. In general, the π–π stacking interactions are stronger than those reported for conventional π–π complexes, which is attributed to the influence of the metal coordination, which is stronger for Zn than either Cd or Hg. The results reported herein might be useful for understanding the solid-state architecture of metal-containing materials that contain M II X 2 subunits and aromatic organic ligands.

scholarly journals A new zinc(II) supramolecular square: Synthesis, crystal structure, thermal behavior and luminescence

2015 ◽  
Vol 80 (10) ◽  
pp. 1289-1295
Author(s):  
Xiu-Yan Wang ◽  
Zhong-Yu Zhao ◽  
Qian Han ◽  
Miao Yu ◽  
De-Yu Kong
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Thermal Behavior ◽  
Luminescence Property ◽  
Room Temperature ◽  
Hydrothermal Condition ◽  
Stacking Interactions ◽  
Triclinic Space Group ◽  
Four Corners ◽  
State Luminescence

A new square-shaped Zn(II) complex, namely, [Zn4(L)4(phen)4]?6H2O (1) (L = 2-hydroxynicotinate and phen = 1,10- phenanthroline), has been synthesized under hydrothermal condition. The crystal of 1 belongs to triclinic, space group P -1 with a = 10.773(2) ?, b = 12.641(3) ?, c = 13.573(3) ?, ? = 107.44(3)?, ? = 102.66(3)?, ? = 93.89(3)?, C72H56N12O18Zn4, Mr = 1638.77, V = 1702.8(6) ?3 , Z = 1, Dc = 1.598 g/cm3 , S = 1.045, ?(MoK?) = 1.475 mm-1 , F(000) = 836, R = 0.0472 and wR = 0.0919. In 1, four L ligands bridge four Zn(II) atoms to form a square-shaped structure, where four phen ligands are respectively located on four corners of the square. The ?-? stacking interactions extend the adjacent squares into a 1D supramolecular chain. The thermal behavior of 1 has been characterized. Moreover, its solid state luminescence property has been studied at room temperature.

scholarly journals Ethyl 8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

2014 ◽  
Vol 70 (6) ◽  
pp. o719-o719 ◽  
Author(s):  
Yoshinobu Ishikawa ◽  
Nanako Yoshida
Keyword(s):  
Hydrogen Bonding ◽  
The Other ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Face To Face ◽  
Compound C ◽  
Centroid Distance ◽  
Benzene Rings ◽  
Translation Symmetry ◽  
Independent Molecules

In the title compound, C13H13NO4, the asymmetric unit contains four independent molecules, each exhibiting an intramolecular N—H...O hydrogen bond. The ethyl group in one of the four molecules is disordered, with a refined occupancy ratio of 0.295 (16):0.705 (16). A face-to-face stacking interaction is found between the benzene rings of the quinoline units of two of the molecules [centroid–centroid distance = 3.541 (2) Å], which are sandwiched by the other two molecules through N—H...O hydrogen bonding. In the crystal, the sandwiched molecules are assembledviastacking interactions along theb-axis direction with their translation-symmetry equivalents [centroid–centroid distance = 3.529 (2) Å], and are further linked through N—H...O hydrogen bonding. The other two molecules are linkedviastacking interactions with their inversion-symmetry equivalents [centroid–centroid distances = 3.512 (3) and 3.716 (4) Å] andviaN—H...O hydrogen bonding.

Supramolecular solid-state patterns generated by hydrogen bonding and π–π stacking interactions in the mononuclear Cr(III) complexes

Polyhedron ◽  
2015 ◽  
Vol 102 ◽  
pp. 410-416 ◽  
Author(s):  
Elena Melnic ◽  
Ecaterina Tocana ◽  
Anatolii V. Siminel ◽  
Lilia Croitor
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Stacking Interactions ◽  
Π Stacking

scholarly journals Hydrogen-Bonding Assembly of Coordination Polymers Showing Reversible Dynamic Solid-State Structural Transformations

Inorganics ◽  
2018 ◽  
Vol 6 (4) ◽  
pp. 115
Author(s):  
Hitoshi Kumagai ◽  
Sadahiro Yagishita ◽  
Ken Kanazashi ◽  
Mariko Ishii ◽  
Shinya Hayami ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Structural Transformation ◽  
Coordination Polymers ◽  
Chain Structure ◽  
Structural Transformations ◽  
The Other ◽  
Ambient Conditions ◽  
Thermally Induced ◽  
Dehydration Processes

We herein report the synthesis, single-crystal structures of coordination polymers, and structural transformations of complexes employing 1,4,5,6-tetrahydro-5,6-dioxo-2,3-pyrazinedicarbonitrile (tdpd2−) and pyrazine (pyz) as bridging ligands. {[M(H2O)4(pyz)][M(tdpd)2(pyz)]·6(H2O)}n, [1·10H2O and 2·10H2O where M = Co (1) and Zn (2)], consists of two types of crystallographically independent one-dimensional (1D) structures packed together. One motif, [M(tdpd)2(pyz)]2− (A), is an anionic infinite pyz bridged 1D array with chelating tdpd2− ligands, and the other motif is a cationic chain, [M(H2O)4(pyz)]2+ (B), which is decorated with four terminal water molecules. The 1D arrays (A) and (B) are arranged in parallel by multi-point hydrogen-bonding interactions in an alternate (A)(B)(A)(B) sequence extending along the c-axis. Both compounds exhibit structural transformations driven by thermal dehydration processes around 350 K to give partially dehydrated forms, 1·2H2O and 2·2H2O. The structural determination of the partially dehydrated form, 2·2H2O, reveals a solid-state structural transformation from a 1D chain structure to a two-dimensional (2D) coordination sheet structure, [Zn2(tdpd)2(H2O)2(pyz)]n (2·2H2O). Further heating to 500 K yields the anhydrous form 2. While the virgin samples of 1·10H2O and 2·10H2O crystallize in different crystal systems, powder X-ray diffraction (PXRD) measurements of the dehydrated forms, 1·2H2O and 2·2H2O, are indicative of the same structure. The structural transformation is irreversible for 1·10H2O at ambient conditions. On the other hand, compound 2·10H2O shows a reversible structural change. The solid-state structural transformation for 1·10H2O was also confirmed by monitoring in-situ magnetic susceptibility, which is consistent with other thermally-induced measurements.

3-Fluoro-2,4,5-triphenylfuran

2007 ◽  
Vol 63 (11) ◽  
pp. o4337-o4337
Author(s):  
Jesse M. Jacobsen ◽  
Satoru Arimitsu ◽  
Gerald B. Hammond ◽  
Mark S. Mashuta
Keyword(s):  
Hydrogen Bonding ◽  
Title Compound ◽  
Phenyl Ring ◽  
Furan Ring ◽  
The Other ◽  
Stacking Interactions ◽  
Compound C ◽  
Π Stacking

The title compound, C22H15FO, is the first example of a crystallographically characterized fully substituted fluorofuran. Although the F atom does not appear to participate in aryl–π attractions or classical hydrogen bonding, the title compound does contain four unique intermolecular π–π stacking interactions that have an atom-to-centroid range of 3.53 (4)–3.64 (4) Å. The phenyl ring located between the F and O atoms is only 9.55 (7)° from being coplanar with the furan ring, whereas the other aromatic planes form angles of 41.71 (1) and 20.45 (1)° with the ring.

Hydrogen-bonding behaviour of benzene-1,2,4,5-tetracarboxylic acid: supramolecular structures of different dimensionality in the 2:1 adducts formed with 4,4′-bipyridyl and hexamethylenetetramine

2000 ◽  
Vol 56 (2) ◽  
pp. 261-272 ◽  
Author(s):  
A. J. Lough ◽  
P. S. Wheatley ◽  
G. Ferguson ◽  
C. Glidewell
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
The Other ◽  
Stacking Interactions ◽  
Tetracarboxylic Acid ◽  
Framework Structure ◽  
Methanol Solutions ◽  
Carboxylate Anions ◽  
A Chain

Co-crystallization of benzene-1,2,4,5-tetracarboxylic acid, C10H6O8, with 4,4′-bipyridyl, C10H8N2, or with hexamethylenetetramine, C6H12N4, from methanol solutions yields in each case a 2:1 salt, [(C10H9N2)+]2·[(C10H4O8)2−] (1) and [(C6H13N4)+]2·[(C10H4O8)2−] (2). In (1) the carboxylate anions lie across centres of inversion, but they contain no intramolecular O—H...O hydrogen bonds: the cations and anions are linked by strong O—H...N and N—H...O hydrogen bonds into a chain-of-rings, and these chains are further linked into a three-dimensional framework structure by means of C—H...O hydrogen bonds and aromatic π...π stacking interactions. Compound (2) contains two independent three-molecule aggregates, comprising a central anion and two cations, linked to the anion by means of short N—H...O hydrogen bonds. One of these aggregates is centrosymmetric, but the other is not, and the two types of anion both form two intramolecular O—H...O hydrogen bonds. The two types of three-molecule aggregate, in which all the anions are virtually parallel, are linked by short C—H...O hydrogen bonds into a molecular staircase.

scholarly journals Hydrogen-bonding patterns in 5-fluorocytosine–melamine co-crystal (4/1)

2016 ◽  
Vol 72 (4) ◽  
pp. 552-555 ◽  
Author(s):  
Marimuthu Mohana ◽  
Packianathan Thomas Muthiah ◽  
Liurukara D. Sanjeewa ◽  
Colin D. McMillen
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
The Other ◽  
Amino Group ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Twofold Axis ◽  
Ring Motif

The asymmetric unit of the title compound, 4C4H4FN3O·C3H6N6, comprises of two independent 5-fluorocytosine (5FC) molecules (AandB) and one half-molecule of melamine (M). The other half of the melamine molecule is generated by a twofold axis. 5FC moleculesAandBare linked through two different homosynthons [R22(8) ring motif]; one is formedviaa pair of N—H...O hydrogen bonds and the secondviaa pair of N—H...N hydrogen bonds. In addition to this pairing, the O atoms of 5FC moleculesAandBinteract with the N2 amino group on both sides of the melamine molecule, forming aDDAAarray of quadruple hydrogen bonds and generating a supramolecular pattern. The 5FC (moleculesAandB) and two melamine molecules interactviaN—H...O, N—H...N and N—H...O, N—H...N, C—H...F hydrogen bonds formingR66(24) andR44(15) ring motifs. The crystal structure is further strengthened by C—H...F, C—F...π and π–π stacking interactions.

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