The Synthesis, Condensation, and Luminescence of Stilbenoid Oligomers with Alkoxysilane End Groups

2001 ◽  
Vol 665 ◽  
Author(s):  
H. Detert ◽  
E. Sugiono
Keyword(s):  
Small Molecules ◽  
Organic Semiconductors ◽  
Three Dimensional ◽  
Synthetic Route ◽  
Heck Reactions ◽  
Transparent Films ◽  
Cross Metathesis ◽  
Fluorescent Materials ◽  
End Groups ◽  
Hydrolysis Of

ABSTRACTA synthetic route to highly luminescent organic semiconductors with curable alkoxysilyl groups is described. Monodisperse oligo(phenylenevinylene)s are rigidly connected to di- and triethoxysilanes via Heck reactions or via cross-metathesis. Hydrolysis of the silicic esters yields silanols condensing to linear and cyclic oligo-OPV-siloxanes or to three-dimensional networks, thus allowing the transformation of small molecules to fluorescent materials with well-defined chromophores. Transparent films are obtained by casting of soluble cyclosiloxanes and from OPV-silanetriols, the latter can be cured to insoluble networks.

Connecting Curable Siloxanes to Luminescent Organic Semiconductors - Monomers for Functional Hybrid Materials

2006 ◽  
Vol 939 ◽  
Author(s):  
Heiner Detert ◽  
Erli Sugiono
Keyword(s):  
Small Molecules ◽  
Organic Semiconductors ◽  
Hybrid Materials ◽  
Three Dimensional ◽  
End Groups ◽  
Rigid Connection ◽  
Hydrolysis Of

ABSTRACTLuminescent stilbenoid chromophores with two alkoxysilane end groups are prepared via hydrosilylation or condensation / reduction of substituted 5-ring OPVs with hydro- and aminopropylsilanes. Chromophore and curable units are connected via flexible spacers. To obtain compounds with a rigid connection between silane and π-system, iodo- or bromo-OPVs were coupled to alkoxysilanes carrying vinyl- or p-vinylphenyl moieties under Heck conditions. This approach allowed a combined connection of the chromophore to the silane moiety with an extension of the π-system. Hydrolysis of the alkoxysilanes yields silanols condensing to curable three-dimensional networks, thus allowing the transformation of small molecules to transparent and fluorescent films with well-defined chromophores.

scholarly journals Global Aromaticity at the Nanoscale

2019 ◽  
Author(s):  
Michel Rickhaus ◽  
Michael Jirasek ◽  
Lara Tejerina ◽  
Henrik Gotfredsen ◽  
Martin D. Peeks ◽  
...  
Keyword(s):  
Small Molecules ◽  
Organic Semiconductors ◽  
Oxidation State ◽  
Single Molecule ◽  
Ring Current ◽  
Electronic Devices ◽  
Three Dimensional ◽  
Average Oxidation State ◽  
Ring Currents ◽  
Cyclic Molecule

<div><p>Aromaticity is an important concept for predicting electronic delocalisation in molecules, particularly for designing organic semiconductors and single-molecule electronic devices. It is most simply defined by the ability of a cyclic molecule to sustain a ring current when placed in a magnetic field. Hückel’s rule states that if a ring has [4n+2] π-electrons, it will be aromatic with an induced magnetisation that opposes the external field inside the ring, whereas if it has 4n π-electrons, it will be antiaromatic with the opposite magnetisation. This rule reliably predicts the behaviour of small molecules, typically with circuits of less than about 22 π-electrons (n = 5). It is not clear whether aromaticity has a size limit and whether Hückel’s rule is valid in much larger macrocycles. Here, we present evidence for global aromaticity in a wide variety of porphyrin nanorings, with circuits of up to 162 π-electrons (n = 40; diameter 5 nm). We show that aromaticity can be controlled by changing the molecular structure, oxidation state and three-dimensional conformation. Whenever a global ring current is observed, its direction is correctly predicted by Hückel’s rule. The magnitude of the current is maximised when the average oxidation state of the porphyrin units is around 0.5–0.7, when the system starts to resemble a conductor with a partially filled valence band. Our results show that aromaticity can arise in large macrocycles, bridging the size gap between ring currents in molecular and mesoscopic rings.</p></div>

scholarly journals Global Aromaticity at the Nanoscale

2019 ◽  
Author(s):  
Michel Rickhaus ◽  
Michael Jirasek ◽  
Lara Tejerina ◽  
Henrik Gotfredsen ◽  
Martin D. Peeks ◽  
...  
Keyword(s):  
Small Molecules ◽  
Organic Semiconductors ◽  
Oxidation State ◽  
Single Molecule ◽  
Ring Current ◽  
Electronic Devices ◽  
Three Dimensional ◽  
Average Oxidation State ◽  
Ring Currents ◽  
Cyclic Molecule

<div><p>Aromaticity is an important concept for predicting electronic delocalisation in molecules, particularly for designing organic semiconductors and single-molecule electronic devices. It is most simply defined by the ability of a cyclic molecule to sustain a ring current when placed in a magnetic field. Hückel’s rule states that if a ring has [4n+2] π-electrons, it will be aromatic with an induced magnetisation that opposes the external field inside the ring, whereas if it has 4n π-electrons, it will be antiaromatic with the opposite magnetisation. This rule reliably predicts the behaviour of small molecules, typically with circuits of less than about 22 π-electrons (n = 5). It is not clear whether aromaticity has a size limit and whether Hückel’s rule is valid in much larger macrocycles. Here, we present evidence for global aromaticity in a wide variety of porphyrin nanorings, with circuits of up to 162 π-electrons (n = 40; diameter 5 nm). We show that aromaticity can be controlled by changing the molecular structure, oxidation state and three-dimensional conformation. Whenever a global ring current is observed, its direction is correctly predicted by Hückel’s rule. The magnitude of the current is maximised when the average oxidation state of the porphyrin units is around 0.5–0.7, when the system starts to resemble a conductor with a partially filled valence band. Our results show that aromaticity can arise in large macrocycles, bridging the size gap between ring currents in molecular and mesoscopic rings.</p></div>

scholarly journals Global Aromaticity at the Nanoscale

2019 ◽  
Author(s):  
Michel Rickhaus ◽  
Michael Jirasek ◽  
Lara Tejerina ◽  
Henrik Gotfredsen ◽  
Martin D. Peeks ◽  
...  
Keyword(s):  
Small Molecules ◽  
Organic Semiconductors ◽  
Oxidation State ◽  
Single Molecule ◽  
Ring Current ◽  
Electronic Devices ◽  
Three Dimensional ◽  
Average Oxidation State ◽  
Ring Currents ◽  
Cyclic Molecule

<div><p>Aromaticity is an important concept for predicting electronic delocalisation in molecules, particularly for designing organic semiconductors and single-molecule electronic devices. It is most simply defined by the ability of a cyclic molecule to sustain a ring current when placed in a magnetic field. Hückel’s rule states that if a ring has [4n+2] π-electrons, it will be aromatic with an induced magnetisation that opposes the external field inside the ring, whereas if it has 4n π-electrons, it will be antiaromatic with the opposite magnetisation. This rule reliably predicts the behaviour of small molecules, typically with circuits of less than about 22 π-electrons (n = 5). It is not clear whether aromaticity has a size limit and whether Hückel’s rule is valid in much larger macrocycles. Here, we present evidence for global aromaticity in a wide variety of porphyrin nanorings, with circuits of up to 162 π-electrons (n = 40; diameter 5 nm). We show that aromaticity can be controlled by changing the molecular structure, oxidation state and three-dimensional conformation. Whenever a global ring current is observed, its direction is correctly predicted by Hückel’s rule. The magnitude of the current is maximised when the average oxidation state of the porphyrin units is around 0.5–0.7, when the system starts to resemble a conductor with a partially filled valence band. Our results show that aromaticity can arise in large macrocycles, bridging the size gap between ring currents in molecular and mesoscopic rings.</p></div>

scholarly journals Monte Carlo simulations of crystalline organic semiconductors

2013 ◽  
Vol 10 (1) ◽  
pp. 125-134
Author(s):  
Marko Mladenovic ◽  
Igor Stankovic
Keyword(s):  
Molecular Structure ◽  
Monte Carlo ◽  
Monte Carlo Simulations ◽  
Small Molecules ◽  
Organic Semiconductors ◽  
Molecular Model ◽  
Three Dimensional

Molecular model for crystalline organic semiconductors based on small molecules is implemented in three-dimensional Monte Carlo simulations. In this paper results for naphthalene are presented. Molecular structure is considered in two configurations: within a single monocrystal and in vicinity of interface between two monocrystals with different crystalline orientations.

A Free Energy Perturbation Approach to Estimate the Intrinsic Solubilities of Drug-like Small Molecules

2019 ◽  
Author(s):  
Sayan Mondal ◽  
Gary Tresadern ◽  
Jeremy Greenwood ◽  
Byungchan Kim ◽  
Joe Kaus ◽  
...  
Keyword(s):  
Solid State ◽  
Small Molecules ◽  
Three Dimensional ◽  
Aqueous Solubility ◽  
Computational Approach ◽  
Free Energy Perturbation ◽  
Perturbation Approach ◽  
Energy Perturbation ◽  
State Form ◽  
Good Agreement

<p>Optimizing the solubility of small molecules is important in a wide variety of contexts, including in drug discovery where the optimization of aqueous solubility is often crucial to achieve oral bioavailability. In such a context, solubility optimization cannot be successfully pursued by indiscriminate increases in polarity, which would likely reduce permeability and potency. Moreover, increasing polarity may not even improve solubility itself in many cases, if it stabilizes the solid-state form. Here we present a novel physics-based approach to predict the solubility of small molecules, that takes into account three-dimensional solid-state characteristics in addition to polarity. The calculated solubilities are in good agreement with experimental solubilities taken both from the literature as well as from several active pharmaceutical discovery projects. This computational approach enables strategies to optimize solubility by disrupting the three-dimensional solid-state packing of novel chemical matter, illustrated here for an active medicinal chemistry campaign.</p>

scholarly journals Functionalization Strategies of PEDOT and PEDOT:PSS Films for Organic Bioelectronics Applications

Chemosensors ◽  
2021 ◽  
Vol 9 (8) ◽  
pp. 212
Author(s):  
Gonzalo E. Fenoy ◽  
Omar Azzaroni ◽  
Wolfgang Knoll ◽  
Waldemar A. Marmisollé
Keyword(s):  
Small Molecules ◽  
Conducting Polymer ◽  
Organic Semiconductors ◽  
Synthesis Method ◽  
Polymer Synthesis ◽  
Preparation Methods ◽  
Electrophysiological Signals ◽  
Organic Bioelectronics ◽  
Biological Interfaces ◽  
Living Organisms

Organic bioelectronics involves the connection of organic semiconductors with living organisms, organs, tissues, cells, membranes, proteins, and even small molecules. In recent years, this field has received great interest due to the development of all kinds of devices architectures, enabling the detection of several relevant biomarkers, the stimulation and sensing of cells and tissues, and the recording of electrophysiological signals, among others. In this review, we discuss recent functionalization approaches for PEDOT and PEDOT:PSS films with the aim of integrating biomolecules for the fabrication of bioelectronics platforms. As the choice of the strategy is determined by the conducting polymer synthesis method, initially PEDOT and PEDOT:PSS films preparation methods are presented. Later, a wide variety of PEDOT functionalization approaches are discussed, together with bioconjugation techniques to develop efficient organic-biological interfaces. Finally, and by making use of these approaches, the fabrication of different platforms towards organic bioelectronics devices is reviewed.

scholarly journals A new synthetic route for the preparation of [Os3(CO)10(μ-OH)(μ-H)] and its reaction with bis(diphenylphosphino)methane (dppm): syntheses and X-ray structures of two isomers of [Os3(CO)8(μ-OH)(μ-H)(μ-dppm)] and [Os3(CO)7(μ3-CO)(μ3-O)(μ-dppm)]

RSC Advances ◽  
2020 ◽  
Vol 10 (73) ◽  
pp. 44699-44711
Author(s):  
Md. Tuhinur R. Joy ◽  
Nikhil C. Bhoumik ◽  
Shishir Ghosh ◽  
Michael G. Richmond ◽  
Shariff E. Kabir
Keyword(s):  
Synthetic Route ◽  
X Ray ◽  
Hydrolysis Of

The cluster [Os3(CO)10(μ-OH)(μ-H)] was obtained in 75% from the hydrolysis of [Os3(CO)10(NCMe)2].

A succinct access to ω-hydroxylated jasmonates via olefin metathesis

2017 ◽  
Vol 72 (7-8) ◽  
pp. 285-292 ◽  
Author(s):  
Guillermo H. Jimenez-Aleman ◽  
Selina Seçinti ◽  
Wilhelm Boland
Keyword(s):  
Abiotic Stress ◽  
Olefin Metathesis ◽  
Higher Plants ◽  
Environmentally Friendly ◽  
Signaling Molecules ◽  
Synthetic Route ◽  
Limited Availability ◽  
Cross Metathesis ◽  
Physiological Processes

AbstractIn higher plants, jasmonates are lipid-derived signaling molecules that control many physiological processes, including responses to abiotic stress, defenses against insects and pathogens, and development. Among jasmonates, ω-oxidized compounds form an important subfamily. The biological roles of these ω-modified derivatives are not fully understood, largely due to their limited availability. Herein, a brief (two-step), simple and efficient (>80% yield), versatile, gram-scalable, and environmentally friendly synthetic route to ω-oxidized jasmonates is described. The approach utilizes olefin cross-metathesis as the key step employing inexpensive, commercially available substrates and catalysts.

Unique three-dimensional (3D) molecular array in dimethyl-DNTT crystals: a new approach to 3D organic semiconductors

2010 ◽  
Vol 1 (2) ◽  
pp. 179 ◽  
Author(s):  
Myeong Jin Kang ◽  
Tatsuya Yamamoto ◽  
Shoji Shinamura ◽  
Eigo Miyazaki ◽  
Kazuo Takimiya
Keyword(s):  
Organic Semiconductors ◽  
Three Dimensional ◽  
New Approach
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