Improved stability of a metallic state in benzothienobenzothiophene-based molecular conductors: an effective increase of dimensionality with hydrogen bonds

2017 ◽  
Vol 53 (24) ◽  
pp. 3426-3429 ◽  
Author(s):  
Toshiki Higashino ◽  
Akira Ueda ◽  
Junya Yoshida ◽  
Hatsumi Mori
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Metallic State ◽  
Molecular Conductors ◽  
Hydrogen Bonding Interactions ◽  
Molecular Conductor ◽  
Improved Stability

Stabilization of a metallic state was successfully achieved by applying hydrogen-bonding interactions in a novel benzothienobenzothiophene-based molecular conductor.

scholarly journals Synthesis, Structure and Physical Properties of (trans-TTF-py2)1.5(PF6)·EtOH: A Molecular Conductor with Weak CH∙∙∙N Hydrogen Bondings

Crystals ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 1081
Author(s):  
Shohei Koyama ◽  
Morio Kawai ◽  
Shinya Takaishi ◽  
Masahiro Yamashita ◽  
Norihisa Hoshino ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Density Functional ◽  
Density Functional Theory Calculation ◽  
Conductivity Measurement ◽  
Stabilization Energy ◽  
Molecular Conductors ◽  
Molecular Conductor ◽  
Theory Calculation

The studies of crystal structures with hydrogen bonds have been actively pursued because of their moderate stabilization energy for constructing unique structures. In this study, we synthesized a molecular conductor based on 2,6-bis(4-pyridyl)-1,4,5,8-tetrathiafulvalene (trans-TTF-py2). Two pyridyl groups were introduced into the TTF skeleton toward the structural exploration in TTF-based molecular conductors involved by hydrogen bonds. In the obtained molecular conductor, (trans-TTF-py2)1.5(PF6)·EtOH, short contacts between the pyridyl group and the hydrogen atom of the TTF skeleton were observed, indicating that hydrogen bonding interactions were introduced in the crystal structure. Spectroscopic measurements and conductivity measurement revealed semiconducting behavior derived from π-stacked trans-TTF-py2 radical in the crystal structure. Finally, these results are discussed with the quantified hydrogen bonding stabilization energy, and the band calculation of the crystal obtained from density functional theory calculation.

scholarly journals 1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid

2009 ◽  
Vol 65 (6) ◽  
pp. o1429-o1429
Author(s):  
Zhen-Dong Zhao ◽  
Yu-Xiang Chen ◽  
Yu-Min Wang ◽  
Liang-Wu Bi
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Molecular Conformation ◽  
Slash Pine ◽  
Carboxyl Groups ◽  
Isopimaric Acid ◽  
Hydrogen Bonding Interactions ◽  
Cyclohexene Ring

The title compound, also known as isopimaric acid, C20H30O2, was isolated from slash pine rosin. There are two unique molecules in the unit cell. The two cyclohexane rings have classical chair conformations. The cyclohexene ring represents a semi-chair. The molecular conformation is stabilized by weak intramolecular C—H...O hydrogen-bonding interactions. The molecules are dimerized through their carboxyl groups by O—H...O hydrogen bonds, formingR22(8) rings.

scholarly journals Hydrogen bonding interactions in single component molecular conductors based on metal (Ni, Au) bis(dithiolene) complexes

2020 ◽  
Vol 49 (18) ◽  
pp. 6056-6064 ◽  
Author(s):  
Hadi Hachem ◽  
Nathalie Bellec ◽  
Marc Fourmigué ◽  
Dominique Lorcy
Keyword(s):  
Hydrogen Bonding ◽  
Closed Shell ◽  
Single Component ◽  
Molecular Conductors ◽  
Hydrogen Bonding Interactions ◽  
Hydrogen Bonded

Nickel (closed-shell) or gold (radical) bis(dithiolene) neutral complexes, functionalized with hydroxyethyl and thiazole moieties, afford hydrogen-bonded single component conductors.

scholarly journals Crystal Structures of Four Novel Thiophene/Phenyl-piperidine Hybrid Chalcones

2014 ◽  
Vol 70 (a1) ◽  
pp. C1020-C1020
Author(s):  
Masood Parvez ◽  
Muhammad Bakhtiar ◽  
Muhammad Baqir ◽  
Muhammad Zia-ur-Rehman
Keyword(s):  
Hydrogen Bonding ◽  
Pharmaceutical Industry ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Benzene Ring ◽  
Drug Targets ◽  
Important Class ◽  
Hydrogen Bonding Interactions ◽  
Benzene Rings ◽  
Type C

Chalcones constitute an important class of bioactive drug targets in the pharmaceutical industry that includes anti-ulcerative drug sofalcone. In continuation of our work, the crystal structures of four closely related 1-phenyl-piperidine based chalcones will be presented. I: C19 H21NOS, MW = 311.43, T = 173(2) K, λ = 0.71073 Å, Orthorhombic, P b c a, a = 10.1045(4), b = 10.5358(4), c = 30.6337(12) Å, V = 3261.2(2) Å3, Z = 8, Dc = 1.269 Mg/m3, F (000) = 1328, R [I>2σ(I)] = 0.059. II: C18H19NOS, MW = 297.40, T = 173(2) K, λ = 1.54178 Å, Orthorhombic, P b c a, a = 8.9236(2), b = 11.0227(2), c = 30.8168(6) Å, V = 3031.21(11) Å3 Z = 8, Dc = 1.303 Mg/m3, F (000) = 1264, R [I>2σ(I)] = 0.035. III: C18H19NOS, MW = 297.40, T = 173(2) K, λ = 1.54178 Å, Orthorhombic, P b c a, a = 8.82990(10), b = 11.0061(2), c = 31.2106(5) Å, V = 3033.13(8) Å3, Z = 8, Dc = 1.303 Mg/m3, F (000) = 1264, R [I>2σ(I)] = 0.048. IV: C18H18ClNOS, MW = 331.84, T = 173(2) K, λ = 0.71073 Å, Monoclinic, P 21/c, a = 14.1037(4), b = 11.3153(3), c = 10.1290(2) Å, β = 101.1367(14)0, V = 1586.02(7) Å3, Z = 4, Dc = 1.390 Mg/m3, F (000) = 696, R [I>2σ(I)] = 0.038. The crystals of I, II and III are isomorphous. In all structures, the piperidine rings are in chair conformations, thiophene rings are essentially planar and the C=C bonds in the prop-2-en-1-one fragment adopt E-conformation. All crystal structures are devoid of any classical hydrogen bonds. However, non-classical hydrogen bonding interactions of the type C---H...O in compounds II, III and IV link the molecules into chains extended along the b-axis. Moreover, C---H...Cg interactions involving thiophene rings in I and III and benzene ring in IV and π...π interactions between benzene rings lying about inversion centers are present in II and III.

Unravelling hydrogen bonding interactions of tryptamine–water dimer from neutral to cation

2017 ◽  
Vol 19 (37) ◽  
pp. 25260-25269 ◽  
Author(s):  
Zongyuan Liu ◽  
Carl O. Trindle ◽  
Quanli Gu ◽  
Wei Wu ◽  
Peifeng Su
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Water Dimer ◽  
Physical Origin ◽  
Intermolecular Hydrogen Bonds ◽  
Hydrogen Bonding Interactions

The physical origin for the three intermolecular hydrogen bonds in the neutral and cationic forms of the tryptamine–water dimer is explored.

Correspondence: Hydrogen Bond to Gold? 1H NMR is Not a Proof of Hydrogen Bonds in Transition Metal Complexes

2018 ◽  
Author(s):  
Jan Vícha ◽  
Cina Foroutan-Nejad ◽  
Michal Straka
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Chemical Shifts ◽  
X Ray ◽  
Structure And Dynamics ◽  
Hydrogen Bonding Interactions ◽  
Overall Stability ◽  
Gold Compounds ◽  
C Nmr

Illusive Au<sup>I/III</sup>···H hydrogen bonds and their effect on structure and dynamics of molecules have been a matter of debate. While a number of X-ray studies reported gold compounds with short Au<sup>I/III</sup>···H contacts, a solid spectroscopic evidence for Au<sup>I/III</sup>···H bonding has been missing. Recently<a></a><a>, Bakar <i>et al.</i></a> (NATURE COMMUNICATIONS 8:576) reported compound with four short Au···H contacts (2.61­–2.66 Å; X-ray determined). Assuming the central cluster be [Au<sub>6</sub>]<sup>2+</sup>and observing the <sup>1</sup>H (<sup>13</sup>C) NMR resonances at relevant H(C) nuclei deshielded with respect to precursor compound, the authors concluded with reservations that <i>“the present Au···H–C interaction is a kind of “hydrogen bond”, where the [Au<sub>6</sub>]<sup>2+</sup>serves as an acceptor”</i>. Here, we show that the Au<sub>6</sub>cluster in their compound bears negative charge and the Au···H contacts lead to a weak (~1 kcal/mol) auride···hydrogen bonding interactions, though unimportant for the overall stability of<b></b>the molecule. Additionally, computational analysis of NMR chemical shifts reveals that the deshielding effects at respective hydrogen nuclei are not directly related to Au···H–C hydrogen bonding .

The design of artificial receptors for complexation and controlled aggregation

1993 ◽  
Vol 345 (1674) ◽  
pp. 57-66 ◽  
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Complex Formation ◽  
Hydrogen Bonds ◽  
Synthetic Receptors ◽  
Polar Solvents ◽  
Artificial Receptors ◽  
Hydrogen Bonding Interactions ◽  
Number Of Factors ◽  
Network Of Hydrogen Bonds

Simple synthetic receptors have been developed that function via directed hydrogen bonding interactions in highly competitive solvents. Strong binding of this type in polar solvents may be due to a number of factors including favourable secondary hydrogen bonding interactions between the carboxylate and urea, the use of charged H-bond acceptors, an inefficient solvation of the closely spaced H-bond donor sites in the urea, and an entropically favourable release of solvent and/or counterion molecules on complex formation. We also demonstrate that these types of interactions can be used to induce, both in solution and the solid state, discrete 2 + 2 aggregates stabilized by a network of hydrogen bonds.

scholarly journals Crystal structure ofcatena-poly[[[triaquastrontium]-di-μ2-glycinato] dibromide]

2015 ◽  
Vol 71 (7) ◽  
pp. 875-878 ◽  
Author(s):  
Palanisamy Revathi ◽  
Thangavelu Balakrishnan ◽  
Kandasamy Ramamurthi ◽  
Subbiah Thamotharan
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Alkaline Earth ◽  
Three Dimensional ◽  
Water Molecules ◽  
Intermolecular Hydrogen Bonds ◽  
Rotation Axes ◽  
Hydrogen Bonding Interactions ◽  
Carboxylate Groups ◽  
Glycine Molecule

In the title coordination polymer, {[Sr(C2H5NO2)2(H2O)3]Br2}n, the Sr2+ion and one of the water molecules are located on twofold rotation axes. The alkaline earth ion is nine-coordinated by three water O atoms and six O atoms of the carboxylate groups of four glycine ligands, two in a chelating mode and two in a monodentate mode. The glycine molecule exists in a zwitterionic form and bridges the cations into chains parallel to [001]. The Br−counter-anions are located between the chains. Intermolecular hydrogen bonds are formed between the amino and carboxylate groups of neighbouring glycine ligands, generating a head-to-tail sequence. Adjacent head-to-tail sequences are further interconnected by intermolecular N—H...Br hydrogen-bonding interactions into sheets parallel to (100). O—H...Br and O—H...O hydrogen bonds involving the coordinating water molecules are also present, consolidating the three-dimensional hydrogen-bonding network.

scholarly journals Photocapture of dynamic hydrogen-bonded assemblies

2004 ◽  
Vol 6 (4) ◽  
pp. 185-192 ◽  
Author(s):  
Nathan D. McClenaghan ◽  
Dario M. Bassani
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Supramolecular Assemblies ◽  
Topochemical Reaction ◽  
Hydrogen Bonding Interactions ◽  
Recent Advances ◽  
Weak Hydrogen Bonding ◽  
Supramolecular Template ◽  
Multiple Hydrogen Bonds ◽  
Hydrogen Bonded

Recent advances in the continuing study of [2+2] photodimerization reactions in supramolecular, non-covalent systems are presented. The covalent photocapture of small dynamic assemblies which are formed using weak hydrogen-bonding interactions between two different complementary units, barbiturates and melamines, is discussed. One unit serves as a photo-inert supramolecular template capable of bringing two photoactive units together using multiple hydrogen-bonds. The second type of unit unites the corresponding, complementary hydrogen-bonding motif with a photoactive unit. Irradiation of the supramolecular assemblies leads to photodimerization of adjacent units and generation of an imprinted site for the template. Moieties which are adapted to participate in photodimerization reactions are styrene, cinnamate, stilbene and fullerene units. The results are interpreted on the basis of topochemical reaction control.

1-[1-(2-Chlorophenyl)ethylidene]thiosemicarbazide

2007 ◽  
Vol 63 (3) ◽  
pp. o1160-o1161 ◽  
Author(s):  
Jian-Gang Wang ◽  
Fang-Fang Jian ◽  
Xiao-Yan Ren ◽  
Shi-Hong Kan
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Room Temperature ◽  
Two Dimensional ◽  
Compound C ◽  
Hydrogen Bonding Interactions

The title compound, C9H10CIN3S, was prepared by the reaction of thiosemicarbazide with 1-(2-chlorophenyl)ethanone at room temperature. The packing is stabilized by hydrogen bonds. In the crystal structure, molecules are linked into two-dimensional layers by intermolecular N—H...S hydrogen-bonding interactions.

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