High-Throughput Pressure-Dependent Density Functional Theory Investigation of Herringbone Polycyclic Aromatic Hydrocarbons: Part 2. Pressure-Dependent Electronic Properties

Hammouri, Mahmoud; Garcia, Taylor M.; Cook, Cameron; Monaco, Stephen; Jezowski, Sebastian R.; Marom, Noa; Schatschneider, Christopher

doi:10.1021/acs.jpcc.8b07307

Cited by 11 publications

(6 citation statements)

References 69 publications

(163 reference statements)

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“…Here, we investigate a series of phenylated acene derivatives, two with tetracene backbones [5,12-diphenyltetracene (DPT) and rubrene (RUB)] and five with pentacene backbones [6-phenylpentacene (MPP), 6,13-diphenylpentacene (DPP), 5,7,12,14-tetraphenyl-pentacene (TPP), 1,4,6,8,11,13-hexaphenylpentacene (HPP), and 1,2,3,4,6,8,9,10,11,13-decaphenylpentacene (DcPP)], whose structures − are illustrated in Figure . Although tetracene and pentacene crystallize in a HB structure, ,− their phenylated derivatives display a rich variety of packing arrangements (Hirshfeld surface analyses of these structures are provided in the Supporting Information). Because of the presence of the phenyl side groups, DPT does not present a HB packing motif but forms π-stacks characterized by cofacial intermolecular interactions (also known as β-HB). , RUB displays a combination of cofacial π-stacking along the b -direction and HB packing in the ab -plane. ,, MPP crystallizes in a “slipped” sandwich HB (SHB) structure with a mixture of cofacial and HB packing, as shown in the Supporting Information.…”

Section: Introductionmentioning

confidence: 99%

Phenylated Acene Derivatives as Candidates for Intermolecular Singlet Fission

et al. 2019

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Singlet fission (SF), a spin-conserving process where one singlet exciton is converted into two triplet excitons, may improve the efficiency of organic photovoltaics. Only a few materials have been experimentally observed to undergo intermolecular SF, most of which are acenes and their derivatives. Using many-body perturbation theory in the GW approximation and the Bethe−Salpeter equation, we systematically investigate the electronic and excitonic properties of tetracene, pentacene, and their phenylated derivatives in the gas phase and solid state. Their potential for SF is evaluated with respect to the thermodynamic driving force and the singlet exciton charge-transfer character. In both the gas phase and solid state, pentacene and its derivatives are more promising than tetracene analogues. Within a family of molecules containing the same acene backbone, increasing the number of phenyl side groups is detrimental for the SF driving force in the gas phase. However, in the solid state, the SF driving force and the exciton character are modulated by intermolecular interactions present within different packing arrangements. Molecules with a higher number of phenyl side groups often form crystals with less cofacial interactions between the acene backbones. These crystals are found to exhibit a higher SF driving force and a higher degree of singlet exciton charge-transfer character.

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Section: Introductionmentioning

confidence: 99%

Phenylated Acene Derivatives as Candidates for Intermolecular Singlet Fission

et al. 2019

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“…The next major contribution (12.7%) is due to NÁ Á ÁH/HÁ Á ÁN interactions, which are clearly classified as van der Waals interactions, because the shortest NÁ Á ÁH distance is over 2.709 Å (between acetonitrile N and indole H atoms), while the sum of the van der Waals radii of the contacting NÁ Á ÁH is around 2.57 Å (Bondi, 1964). Finally, the presence of CÁ Á ÁC (1.0%) and CÁ Á ÁN/NÁ Á ÁC (0.3%) contacts corresponding to theinteractions contributes a small part of the surface and may suggests a less ideal packing arrangement for the molecule in the crystal (Hammouri et al, 2018).…”

Section: Figurementioning

confidence: 99%

Synthesis, structure and antiproliferative and optical activities of two new biphenyl-derived Schiff bases

et al. 2019

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Two novel Schiff bases derived from indole and biphenyl have been designed and synthesized, namely 3‐((E)‐{(E)‐[1‐(biphenyl‐4‐yl)ethylidene]hydrazinylidene}methyl)‐1‐methyl‐1H‐indole (3‐BEHMI) acetonitrile monosolvate, C24H21N3·CH3CN, and 3‐((E)‐{(E)‐[1‐(biphenyl‐4‐yl)ethylidene]hydrazinylidene}methyl)‐1‐methyl‐1H‐indole (3‐BEHEI) acetonitrile monosolvate, C24H21N3·CH3CN. Their structures were characterized by elemental analysis, quadrupole time‐of‐flight MS, NMR and UV–Vis spectroscopy. The single‐crystal packing structure of 3‐BEHMI is largely dominated by C—H…π interactions and weak van der Waals interactions. The in vitro cytotoxicity of the two title compounds have been evaluated against two tumour cell lines (A549 human lung cancer and 4T1 mouse breast cancer) and two normal cell lines (MRC‐5 normal lung cells and NIH 3T3 fibroblasts) by MTT assay. The results indicate that 3‐BEHEI exhibits a slightly weaker antiproliferative capability (IC50 = ∼50 µM) than the previously reported similar Schiff base 3‐BEHI (IC50 = ∼20 µM). This is in line with docking results. 3‐BEHMI demonstrates a weak cytotoxic activity, with IC50 values around 110 µM, which disagrees with its docking results. Overall, the tested compounds manifest relevant cytotoxicities on the selected cancer cell lines and normal cell lines. The UV–Vis and fluorescence spectra were recorded and reproduced through the TD‐DFT method with four types of hybrid density functionals, including B3LYP, M062X, PBE1PBE and WB97XD.

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“…In many applications of computational high-pressure chemistry, DFT using PBCs is the method of choice. [166][167][168][169][170] In this Section, however, care is exercised to present applications using other methods as well, for example, wall potentials, mixed quantum mechanical/molecular mechanics (QM/MM) approaches, Quantum Monte Carlo, and single-molecule methods such as (X-)HCFF, XP-PCM, and GOSTSHYP.…”

Section: Applicationsmentioning

confidence: 99%

Computational high‐pressure chemistry: Ab initio simulations of atoms, molecules, and extended materials in the gigapascal regime

Zeller,

Hsieh,

Dononelli

et al. 2024

WIREs Comput Mol Sci

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The field of liquid‐phase and solid‐state high‐pressure chemistry has exploded since the advent of the diamond anvil cell, an experimental technique that allows the application of pressures up to several hundred gigapascals. To complement high‐pressure experiments, a large number of computational tools have been developed. These techniques enable the simulation of chemical systems, their sizes ranging from single atoms to infinitely large crystals, under high pressure, and the calculation of the resulting structural, electronic, and spectroscopic changes. At the most fundamental level, computational methods using carefully tailored wall potentials allow the analytical calculation of energies and electronic properties of compressed atoms. Molecules and molecular clusters can be compressed either via mechanochemical approaches or via more sophisticated computational protocols using implicit or explicit solvation approaches, typically in combination with density functional theory, thus allowing the simulation of pressure‐induced chemical reactions. Crystals and other periodic systems can be routinely simulated under pressure as well, both statically and dynamically, to predict the changes of crystallographic data under pressure and high‐pressure crystal structure transitions. In this review, the theoretical foundations of the available computational tools for simulating high‐pressure chemistry are introduced and example applications demonstrating the strengths and weaknesses of each approach are discussed.This article is categorized under: Structure and Mechanism > Computational Materials Science Electronic Structure Theory > Ab Initio Electronic Structure Methods Software > Simulation Methods

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High-Throughput Pressure-Dependent Density Functional Theory Investigation of Herringbone Polycyclic Aromatic Hydrocarbons: Part 2. Pressure-Dependent Electronic Properties

Cited by 11 publications

References 69 publications

Phenylated Acene Derivatives as Candidates for Intermolecular Singlet Fission

Phenylated Acene Derivatives as Candidates for Intermolecular Singlet Fission

Synthesis, structure and antiproliferative and optical activities of two new biphenyl-derived Schiff bases

Computational high‐pressure chemistry: Ab initio simulations of atoms, molecules, and extended materials in the gigapascal regime

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