Understanding the solid state luminescence and piezochromic properties in polymorphs of an anthracene derivative

Aziz, Alex; Sidat, Amir; Talati, Priyesh; Crespo‐Otero, Rachel

doi:10.1039/d1cp05192j

Cited by 7 publications

(7 citation statements)

References 77 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There have been 8 polymorphs of 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile, commonly known as ROY, and their electronic band gaps have been calculated to be 1.12–1.84 eV depending on crystal structures . In another case, band gaps of two polymorphs of 9,10-bis((E)-2-(pyridin-4-yl)vinyl)anthracene (BP4VA) have been reported to be 1.58 and 1.26 eV in the literature . Using the trained model, medium CrystGraph of ROY afforded 0.40 eV MAE, and BP4PV resulted in 0.52 eV MAE (Figure ).…”

Section: Resultsmentioning

confidence: 99%

“… 30 In another case, band gaps of two polymorphs of 9,10-bis((E)-2-(pyridin-4-yl)vinyl)anthracene (BP4VA) have been reported to be 1.58 and 1.26 eV in the literature. 31 Using the trained model, medium CrystGraph of ROY afforded 0.40 eV MAE, and BP4PV resulted in 0.52 eV MAE ( Figure 6 ). The result, a smaller error of ROY than BP4VA, may be attributed to the difference in a polymorphic manner.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Graph Comparison of Molecular Crystals in Band Gap Prediction Using Neural Networks

Taniguchi,

Hosokawa,

Asahi

2023

ACS Omega

View full text Add to dashboard Cite

In material informatics, the representation of the material structure is fundamentally essential to obtaining better prediction results, and graph representation has attracted much attention in recent years. Molecular crystals can be graphically represented in molecular and crystal representations, but a comparison of which representation is more effective has not been examined. In this study, we compared the prediction accuracy between molecular and crystal graphs for band gap prediction. The results showed that the prediction accuracies using crystal graphs were better than those obtained using molecular graphs. While this result is not surprising, error analysis quantitatively evaluated that the error of the crystal graph was 0.4 times that of the molecular graph with moderate correlation. The novelty of this study lies in the comparison of molecular crystal representations and in the quantitative evaluation of the contribution of crystal structures to the band gap.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Graph Comparison of Molecular Crystals in Band Gap Prediction Using Neural Networks

Taniguchi,

Hosokawa,

Asahi

2023

ACS Omega

View full text Add to dashboard Cite

show abstract

“…239 DFT using PBCs or QM/MM approaches are often used to identify the intermolecular interactions responsible for this effect, for example, π À π and CH À π interactions (Figure 7). [240][241][242][243][244] In a mixed experimental/ computational study, it was found that intermolecular interactions may even become so strong under pressure that an electron can be transferred, which has tremendous influence on the piezochromic behavior of the system. 245 At the molecular level, minute changes in dihedral angles, for example, those modulating the overlap of neighboring π systems, or the planarity of individual π systems play an important role in piezochromic behavior.…”

Section: Spectroscopic Properties: Piezochromism and Vibrational Spectramentioning

confidence: 99%

“…DFT using PBCs or QM/MM approaches are often used to identify the intermolecular interactions responsible for this effect, for example,

\pi -\pi

and

\mathrm{CH}-\pi

interactions (Figure 7). 240–244 In a mixed experimental/computational study, it was found that intermolecular interactions may even become so strong under pressure that an electron can be transferred, which has tremendous influence on the piezochromic behavior of the system 245 …”

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

View full text Add to dashboard Cite

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

show abstract

“…The mechanical deformation of a molecular material leads to structural changes at the atomic level in the form of modifications in the geometries of its constituent molecules or, in case a crystal is considered, its crystal lattice parameters. These mechanically induced geometric changes at the atomic level can give rise to spectroscopic signals, which can be exploited in the design of mechano-1,2 and piezochromic [3][4][5] materials. Of particular interest in this regard are mechanophores, i.e., small molecular units that respond to mechanical deformation by profound structural changes such as bond rupture.…”

Section: Introductionmentioning

confidence: 99%

JEDI: A versatile code for strain analysis of molecular and periodic systems under deformation

Wang,

Benter,

Dononelli

et al. 2024

Preprint

View full text Add to dashboard Cite

Stretching or compression can induce significant energetic, geometric and spectroscopic changes in materials. To fully exploit these effects in the design of mechano- or piezochromic materials, self-healing polymers, and other mechanoresponsive devices, a detailed knowledge about the distribution of mechanical strain in the material is essential. Within the past decade, the Judgement of Energy DIstribution (JEDI) analysis has emerged as a useful tool for this purpose. Based on the harmonic approximation, the strain energy in each bond length, bond angle and dihedral angle of a deformed system is calculated using quantum chemical methods. This allows the identification of the force-bearing scaffold of the system, leading to an understanding of mechanochemical processes at the most fundamental level. Here we present a publicly available code that generalizes the JEDI analysis, which has previously only been available for isolated molecules. Now the code has been extended to two- and three-dimensional periodic systems, supramolecular clusters, and substructures of chemical systems under various types of deformation. Due to the implementation of JEDI into the Atomic Simulation Environment (ASE), the JEDI analysis can be interfaced with a plethora of program packages that allow the calculation of electronic energies for molecular systems and systems with periodic boundary conditions. The automated generation of a color-coded three-dimensional structure via the Visual Molecular Dynamics (VMD) program allows insightful visual analyses of the force-bearing scaffold of the strained system.

show abstract

Understanding the solid state luminescence and piezochromic properties in polymorphs of an anthracene derivative

Abstract: Luminescent molecular crystals have gained significant research interest for optoelectronic applications. However, fully understanding their structural and electronic relationships in the condensed phase and under external stimuli remains a significant...

Cited by 7 publications

References 77 publications

Graph Comparison of Molecular Crystals in Band Gap Prediction Using Neural Networks

Graph Comparison of Molecular Crystals in Band Gap Prediction Using Neural Networks

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

JEDI: A versatile code for strain analysis of molecular and periodic systems under deformation

Contact Info

Product

Resources

About