scholarly journals Functional materials based on molecules with hydrogen-bonding ability: applications to drug co-crystals and polymer complexes

2018 ◽  
Vol 5 (6) ◽  
pp. 180564 ◽  
Author(s):  
Kristin M. Hutchins
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Functional Materials ◽  
Polymeric Materials ◽  
Pharmaceutical Compounds ◽  
Multiple Point ◽  
Polymer Complexes ◽  
Design Synthesis ◽  
Hydrogen Bonding Interactions ◽  
Donor Acceptor

The design, synthesis and property characterization of new functional materials has garnered interest in a variety of fields. Materials that are capable of recognizing and binding with small molecules have applications in sensing, sequestration, delivery and property modification. Specifically, recognition of pharmaceutical compounds is of interest in each of the aforementioned application areas. Numerous pharmaceutical compounds comprise functional groups that are capable of engaging in hydrogen-bonding interactions; thus, materials that are able to act as hydrogen-bond receptors are of significant interest for these applications. In this review, we highlight some crystalline and polymeric materials that recognize and engage in hydrogen-bonding interactions with pharmaceuticals or small biomolecules. Moreover, as pharmaceuticals often exhibit multiple hydrogen-bonding sites, many donor/acceptor molecules have been specifically designed to interact with the drug via such multiple-point hydrogen bonds. The formation of multiple hydrogen bonds not only increases the strength of the interaction but also affords unique hydrogen-bonded architectures.

A Neutral Donor-Acceptor p-Stack: Solid-State Structures of 1 : 1 Pyromellitic Diimide-Dialkoxynaphthalene Cocrystals

1997 ◽  
Vol 50 (5) ◽  
pp. 439 ◽  
Author(s):  
Darren G. Hamilton ◽  
Daniel E. Lynch ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Neutral Donor ◽  
Hydrogen Bonding Interactions ◽  
Donor And Acceptor ◽  
Structural Preferences ◽  
Donor Acceptor ◽  
Covalently Linked ◽  
Solid State Structures

Pyromellitic diimide forms orange-coloured cocrystals of 1 : 1 stoichiometry with dialkoxynaphthalene derivatives. The solid-state structures of two examples are presented. The cocrystal formed with 2,6-dimethoxynaphthalene presents vertical stacks of alternating π-rich and π-deficient subunits with the long axes of the respective components approximately parallel. Investigation of the packing in the cocrystal also reveals a stabilizing array of hydrogen bonds between the components of adjacent stacks. Cocrystallization with 1,5-[2-(2-hydroxyethoxy)ethoxy]naphthalene, a derivative bearing hydroxy terminated ethyleneoxy chains, gives rise to an altered structural arrangement. Alternating donor- acceptor stacks once again dominate the structure but adopt a geometry where the long axes of the constituents are essentially perpendicular. Hydrogen-bonding interactions result in the formation of continuous non-covalently linked columns of donor and acceptor subunits by linking the terminal hydroxy functions of the naphthalene component to the imide protons. The structural preferences revealed by these solid-state analyses indicate that these complexes are useful prototypes of more complex neutral supramolecular assemblies.

Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogen-bonding sites

2012 ◽  
Vol 68 (4) ◽  
pp. 431-443 ◽  
Author(s):  
Maya Tutughamiarso ◽  
Guido Wagner ◽  
Ernst Egert
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Antiviral Drug ◽  
The Other ◽  
Receptor Interaction ◽  
Dimer Formation ◽  
Hydrogen Bonding Interactions ◽  
Donor Acceptor ◽  
Drug Receptor ◽  
Drug Receptor Interaction

The antifungal drug 5-fluorocytosine (4-amino-5-fluoro-1,2-dihydropyrimidin-2-one) was cocrystallized with five complementary compounds in order to better understand its drug–receptor interaction. The first two compounds, 2-aminopyrimidine (2-amino-1,3-diazine) and N-acetylcreatinine (N-acetyl-2-amino-1-methyl-5H-imidazol-4-one), exhibit donor–acceptor sites for R 2 2(8) heterodimer formation with 5-fluorocytosine. Such a heterodimer is observed in the cocrystal with 2-aminopyrimidine (I); in contrast, 5-fluorocytosine and N-acetylcreatinine [which forms homodimers in its crystal structure (II)] are connected only by a single hydrogen bond in (III). The other three compounds 6-aminouracil (6-amino-2,4-pyrimidinediol), 6-aminoisocytosine (2,6-diamino-3H-pyrimidin-4-one) and acyclovir [acycloguanosine or 2-amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one] possess donor–donor–acceptor sites; therefore, they can interact with 5-fluorocytosine to form a heterodimer linked by three hydrogen bonds. In the cocrystals with 6-aminoisocytosine (Va)–(Vd), as well as in the cocrystal with the antiviral drug acyclovir (VII), the desired heterodimers are observed. However, they are not formed in the cocrystal with 6-aminouracil (IV), where the components are connected by two hydrogen bonds. In addition, a solvent-free structure of acyclovir (VI) was obtained. A comparison of the calculated energies released during dimer formation helped to rationalize the preference for hydrogen-bonding interactions in the various cocrystal structures.

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.

A room-temperature self-healing elastomer with ultra-high strength and toughness fabricated via optimized hierarchical hydrogen-bonding interactions

2022 ◽  
Author(s):  
Liangliang Xia ◽  
Ming Zhou ◽  
Hongjun Tu ◽  
wen Zeng ◽  
xiaoling Yang ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Mechanical Strength ◽  
Room Temperature ◽  
Polymeric Materials ◽  
High Strength ◽  
Self Healing ◽  
High Mechanical Strength ◽  
Hydrogen Bonding Interactions ◽  
Healing Efficiency ◽  
Good Healing

The preparation of room-temperature self-healing polymeric materials with good healing efficiency and high mechanical strength is challenging. Two processes are essential to realise the room-temperature self-healing of materials: (a) a...

scholarly journals Recent Progress in Hydrogen-Bonded π-Conjugated Systems Displaying J-Type Aggregates

2020 ◽  
Vol 02 (01) ◽  
pp. 047-063 ◽  
Author(s):  
Nelson Ricardo Ávila-Rovelo ◽  
Amparo Ruiz-Carretero
Keyword(s):  
Hydrogen Bonding ◽  
Self Assembly ◽  
Noncovalent Interactions ◽  
Functional Materials ◽  
Organic Electronic Devices ◽  
Conjugated Systems ◽  
Hydrogen Bonding Interactions ◽  
Different Types ◽  
J Aggregates ◽  
Additional Hydrogen

Supramolecular approaches are of great interest in the design of functional materials. The types of aggregates arising from different noncovalent interactions endow materials with intriguing properties. In this sense, J-type aggregates are very attractive due to their unique optical properties and capacity to transport excitons. These features make them great candidates in the design of materials for organic electronic devices. Furthermore, the incorporation of additional hydrogen-bonding functionalities provides J-aggregates with superior directionality and connection among the different π-conjugated cores. The control over the formation of H-bonds to achieve functional aggregates is therefore a promising strategy towards controlled structures with specific functions.This review outlines the most relevant and recent works of π-conjugated systems exhibiting J-type aggregates resulting from hydrogen-bonding interactions. Different types of hydrogen-bonding functionalities will be discussed together with their roles in the aggregate properties, their impact in the optoelectronic properties, the self-assembly mechanisms, and their applications in organic electronics.

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.

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 {N 1-[2-(Butylselanyl)benzyl]-N 2,N 2-dimethylethane-1,2-diamine}dichloridomercury(II)

2018 ◽  
Vol 74 (8) ◽  
pp. 1151-1154
Author(s):  
Pushpendra Singh ◽  
Harkesh B. Singh ◽  
Ray J. Butcher
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Self Assembly ◽  
Title Compound ◽  
Supramolecular Assembly ◽  
Molecular Geometry ◽  
The Self ◽  
Intermolecular Hydrogen Bonding ◽  
Hydrogen Bonding Interactions ◽  
Donor Acceptor

In the title compound, [HgCl2(C16H28N2Se)], the primary geometry around the Se and Hg atoms is distorted trigonal–pyramidal and distorted square-pyramidal, respectively. The distortion of the molecular geometry in the complex is caused by the steric demands of the ligands attached to the Se atom. The Hg atom is coordinated through two chloride anions, an N atom and an Se atom, making up an unusual HgNSeCl2 coordination sphere with an additional long Hg...N interaction. Intermolecular C—H...Cl interactions are the only identified intermolecular hydrogen-bonding interactions that seem to be responsible for the self assembly. These relatively weak C—H...Cl hydrogen bonds possess the required linearity and donor–acceptor distances. They act as molecular associative forces that result in a supramolecular assembly along the b-axis direction in the solid state of the title compound.

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