Study of stacking interactions between two neutral tetrathiafulvalene molecules in Cambridge Structural Database crystal structures and by quantum chemical calculations

Antonijević, Ivana S.; Malenov, Dušan P.; Hall, Michael B.; Zarić, Snežana D.

doi:10.1107/s2052520618015494

Cited by 9 publications

(3 citation statements)

References 66 publications

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“…Stacking is not limited to aromatic rings. There have been several papers on the stacking (with each other or with aromatic rings) of delocalized chelate rings, rings formed by intramolecular H-bonds, or other nonaromatic systems such as neutral tetrathiafulvalene. − Some of these interactions can be face-to-face, or nearly so.…”

Section: Fundamental Sciencementioning

confidence: 99%

A Million Crystal Structures: The Whole Is Greater than the Sum of Its Parts

2019

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The founding in 1965 of what is now called the Cambridge Structural Database (CSD) has reaped dividends in numerous and diverse areas of chemical research. Each of the million or so crystal structures in the database was solved for its own particular reason, but collected together, the structures can be reused to address a multitude of new problems. In this Review, which is focused mainly on the last 10 years, we chronicle the contribution of the CSD to research into molecular geometries, molecular interactions, and molecular assemblies and demonstrate its value in the design of biologically active molecules and the solid forms in which they are delivered. Its potential in other commercially relevant areas is described, including gas storage and delivery, thin films, and (opto)electronics. The CSD also aids the solution of new crystal structures. Because no scientific instrument is without shortcomings, the limitations of CSD research are assessed. We emphasize the importance of maintaining database quality: notwithstanding the arrival of big data and machine learning, it remains perilous to ignore the principle of garbage in, garbage out. Finally, we explain why the CSD must evolve with the world around it to ensure it remains fit for purpose in the years ahead.

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Section: Fundamental Sciencementioning

confidence: 99%

A Million Crystal Structures: The Whole Is Greater than the Sum of Its Parts

2019

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“…[ 31,32 ] TTF is a kind of heterocyclic organic compounds and has excellent conductivity with a redox potential of 0.05 V, which is the proper potential for transfer of electrons between mediator and FAD cofactor having redox potential of −0.46 V. In addition, due to its unique heterocyclic chemical structure, TTF interacts with GOx by π−π interaction, enhancing adhesion between them. [ 33 ] As shown in Figure 3a, the onset potential of GOR observed in flat Au anode with PTFE substrate was 0.05 V, with current density of 0.37 mA cm −2 at 0.3 V. These were 0.05 V and 0.31 mA cm −2 at 0.3 V in non‐buckled flat Au anode on PDMS substrate (Figure 3c). Interestingly, those measured with buckled Au anode on PDMS substrate were 0.05 V and 0.39 mA cm −2 at 0.3 V (Figure 3e).…”

Section: Resultsmentioning

confidence: 91%

Stretchable Enzymatic Biofuel Cells Based on Microfluidic Structured Elastomeric Polydimethylsiloxane with Wrinkled Gold Electrodes

Lee,

Kim,

Kwon

et al. 2023

Adv Funct Materials

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Various sensors and electronic devices are recently developed to monitor human health in mechanically flexible or even stretchable forms for intimate contact with non‐flat curvilinear surfaces of the human body. For successful operation of these devices, finding a proper way to electrically power them is very important. In this work, glucose/oxygen fueled enzymatic biofuel cells (EBFCs) based on microfluidic structured elastomeric polydimethylsiloxane substrate with wrinkled gold (Au) electrodes are suggested for power supply. For doing that, firstly, bottom surface of microfluidic channel is covered with buckled Au electrodes for stretchability. By microfluidic design showing capillary imbibition through fluidic channels, loading of catalyts is promoted. Interestingly, buckled Au electrodes induce much better anodic and cathodic reaction rates than those of non‐buckled Au electrodes by 25% and 33%, respectively. This is because surface area and the amount of catalyst loading in electrodes increase by Au wrinkling. In evaluations of EBFCs using the buckled Au electrodes, maximum power density reaches 7.1 ± 0.64 µW cm−2, while they show decent performance of 5.4 ± 0.49 µW cm−2 even under external stretching. Taken together, it is corroborated that such proposed stretchable EBFCs are alternative for providing electrical power in wearable or implantable devices.

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“…The stability of molecular crystal surfaces may be attributed to the strength of the intermolecular interactions being cleaved and the chemical groups exposed on the surface. 63 The (111) facet, shown in Figure 3a, cleaves through the strong interactions in stacking direction of the TTF molecules 107 and exposes the electron-rich π-system and the sulfur atoms of TTF on the surface. Therefore, this facet has a relatively high surface energy.…”

Section: ■ Introductionmentioning

confidence: 99%

Structure Prediction of Epitaxial Organic Interfaces with Ogre, Demonstrated for Tetracyanoquinodimethane (TCNQ) on Tetrathiafulvalene (TTF)

et al. 2023

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Highly ordered epitaxial interfaces between organic semiconductors are considered as a promising avenue for enhancing the performance of organic electronic devices including solar cells and transistors, thanks to their well-controlled, uniform electronic properties and high carrier mobilities. The electronic structure of epitaxial organic interfaces and their functionality in devices are inextricably linked to their structure. We present a method for structure prediction of epitaxial organic interfaces based on lattice matching followed by surface matching, implemented in the open-source Python package, Ogre. The lattice matching step produces domain-matched interfaces, where commensurability is achieved with different integer multiples of the substrate and film unit cells. In the surface matching step, Bayesian optimization (BO) is used to find the interfacial distance and registry between the substrate and film. The BO objective function is based on dispersion corrected deep neural network interatomic potentials. These are shown to be in qualitative agreement with density functional theory (DFT) regarding the optimal position of the film on top of the substrate and the ranking of putative interface structures. Ogre is used to investigate the epitaxial interface of 7,7,8,8-tetracyanoquinodimethane (TCNQ) on tetrathiafulvalene (TTF), whose electronic structure has been probed by ultraviolet photoemission spectroscopy (UPS), but whose structure had been hitherto unknown [Organic Electronics 2017, 48, 371]. We find that TCNQ(001) on top of TTF(100) is the most stable interface configuration, closely followed by TCNQ(010) on top of TTF(100). The density of states, calculated using DFT, is in excellent agreement with UPS, including the presence of an interface charge transfer state.

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Study of stacking interactions between two neutral tetrathiafulvalene molecules in Cambridge Structural Database crystal structures and by quantum chemical calculations

Cited by 9 publications

References 66 publications

A Million Crystal Structures: The Whole Is Greater than the Sum of Its Parts

A Million Crystal Structures: The Whole Is Greater than the Sum of Its Parts

Stretchable Enzymatic Biofuel Cells Based on Microfluidic Structured Elastomeric Polydimethylsiloxane with Wrinkled Gold Electrodes

Structure Prediction of Epitaxial Organic Interfaces with Ogre, Demonstrated for Tetracyanoquinodimethane (TCNQ) on Tetrathiafulvalene (TTF)

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