TD-DFT based fine-tuning of molecular excitation energies using evolutionary algorithms

Abburu, Sailesh; Venkatraman, Vishwesh; Alsberg, Bjørn K.

doi:10.1039/c5ra22800j

Cited by 5 publications

(5 citation statements)

References 79 publications

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“…This flexibility stems from the customizable molecular builder that offers control of the synthetic accessibility of the candidates at the same time as allowing for the automated construction even of short-lived intermediates, transition states, ion pairs, and supramolecules . These capabilities have been utilized in the de novo design of a range of different compounds, including ruthenium-based olefin metathesis catalysts, azobenzenes with tailored excitation energies, dyes for solar cells, , monomers for high-refractive-index organic polymers, organic solvents for CO 2 capture, and iron-based spin-crossover compounds . One of the last iron complexes was later confirmed, in experiments, to possess spin-crossover properties and is thus, to our knowledge, the first automatically de novo designed inorganic molecule experimentally verified to reflect the intended properties .…”

Section: Software Packages For Catalyst Designmentioning

confidence: 99%

Automated in Silico Design of Homogeneous Catalysts

2020

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Catalyst discovery is increasingly relying on computational chemistry, and many of the computational tools are currently being automated. The state of this automation and the degree to which it may contribute to speeding up development of catalysts are the subject of this Perspective. We also consider the main challenges associated with automated catalyst design, in particular the generation of promising and chemically realistic candidates, the tradeoff between accuracy and cost in estimating the catalytic performance, the opportunities associated with automated generation and use of large amounts of data, and even how to define the objectives of catalyst design. Throughout the Perspective, we take a cross-disciplinary approach and evaluate the potential of methods and experiences from fields other than homogeneous catalysis. Finally, we provide an overview of software packages available for automated in silico design of homogeneous catalysts.

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Section: Software Packages For Catalyst Designmentioning

confidence: 99%

Automated in Silico Design of Homogeneous Catalysts

2020

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“…DENOPTIM has been used to fine-tune azobenzene excitation energies. 39 The absorption maximum of each candidate was estimated using time-dependent density functional theory (TD-DFT) and used as fitness function. Starting from 300 known azobenzenes (λ max 318−575 nm), DENOPTIM identified novel compounds with a predicted λ max higher than 600 nm.…”

Section: Journal Of Chemical Information and Modelingmentioning

confidence: 99%

“…DENOPTIM has been used to fine-tune azobenzene excitation energies . The absorption maximum of each candidate was estimated using time-dependent density functional theory (TD-DFT) and used as fitness function.…”

Section: Application Examplesmentioning

confidence: 99%

DENOPTIM: Software for Computational de Novo Design of Organic and Inorganic Molecules

Foscato

Venkatraman

Jensen

2019

J. Chem. Inf. Model.

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A general-purpose software package, termed DE Novo OPTimization of In/organic Molecules (DENOPTIM), for de novo design and virtual screening of functional molecules is described. Molecules of any element and kind, including metastable species and transition states, are handled as chemical objects that go beyond valence-rules representations. Synthetic accessibility of the generated molecules is ensured via detailed control of the kinds of bonds that are allowed to form in the automated molecular building process. DENOPTIM contains a combinatorial explorer for screening and a genetic algorithm for global optimization of user-defined properties. Estimates of these properties may be obtained to form the fitness function (figure of merit or scoring function) from external molecular modeling programs via shell scripts. Examples of a range of different fitness functions and DENOPTIM applications, including an easy-to-do test case, are described. DENOPTIM is available as Open Source from .

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“…While this relatively new class of azoarene photoswitches is attractive, the complete enumeration of the chemical space approaches 10 6 . Density functional theory (DFT) calculations are used to predict structures and photophysical properties at a relatively low computational cost. , Thus, DFT has been previously used in high-throughput virtual screening (HTVS) − for virtual libraries containing 500–500 000 molecules. The vastness of the chemical space cannot be understated; conservative estimates suggest that at least 10 23 organic molecules are theoretically possible .…”

Section: Introductionmentioning

confidence: 99%

Efficient Discovery of Visible Light-Activated Azoarene Photoswitches with Long Half-Lives Using Active Search

Mukadum

Nguyen

Adrion

et al. 2021

J. Chem. Inf. Model.

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Photoswitches are molecules that undergo a reversible, structural isomerization after exposure to different wavelengths of light. The dynamic control offered by molecular photoswitches is favorable for applications in materials chemistry, photopharmacology, and catalysis. Ideal photoswitches absorb visible light and have long-lived metastable isomers. We used high throughput virtual screening to predict the absorption maxima (λ max ) of the E-isomer and half-lives (t 1/2 ) of the Z-isomer. However, computing the photophysical and kinetic properties of each entry of a virtual molecular library containing 10 3 -10 6 entries with density functional theory is prohibitively time-consuming. We applied active search, a machine learning technique to intelligently search a chemical search space of 255 991 photoswitches based on 29 known azoarenes and their derivatives. We iteratively trained the active search algorithm based on whether a candidate absorbed visible light (λ max > 450 nm). Active search was found to triple the discovery 1 rate compared to random search. Further, we projected 1 962 photoswitches to 2D using the Uniform Manifold Approximation and Projection (umap) algorithm and found that λ max depends on the core, which is tunable with substituents. We then incorporated a second stage of screening with to predict the stabilities of the Z-isomers for the top 1% of candidates. We identified four ideal photoswitches that concurrently satisfy λ max > 450 nm and t 1/2 > 2 hours; the range of λ max and t 1/2 range from 465 to 531 nm and hours to days, respectively.

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TD-DFT based fine-tuning of molecular excitation energies using evolutionary algorithms

Abstract: An evolutionary de novo design method is presented to fine-tune the excitation energies of molecules calculated using time-dependent density functional theory (TD-DFT).

Cited by 5 publications

References 79 publications

Automated in Silico Design of Homogeneous Catalysts

Automated in Silico Design of Homogeneous Catalysts

DENOPTIM: Software for Computational de Novo Design of Organic and Inorganic Molecules

Efficient Discovery of Visible Light-Activated Azoarene Photoswitches with Long Half-Lives Using Active Search

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