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Title: Uncovering novel liquid organic hydrogen carriers: a systematic exploration of chemical compound space using cheminformatics and quantum chemical methods

Journal Article · · Digital Discovery
DOI: https://doi.org/10.1039/d3dd00123g · OSTI ID:2009005

We present a comprehensive, in silico-based discovery approach to identifying novel liquid organic hydrogen carrier (LOHC) candidates using cheminformatics methods and quantum chemical calculations. We screened over 160 billion molecules from ZINC15 and GDB-17 chemical databases for structural similarity to known LOHCs and employed a data-driven selection criterion connecting molecular features with dehydrogenation enthalpy. This scoring criterion effectively predicts dehydrogenation enthalpies from SMILES strings, streamlining the LOHC screening process. After rigorous screening and down-selection, we compiled a database of 3000 dehydrogenation reactions for the most promising LOHC candidates, setting the stage for future selection based on kinetics and catalysis. This work demonstrates the significant impact of integrating quantum chemistry and cheminformatics in materials discovery, accelerating the selection process while reducing experimental efforts and time. By proposing new molecules as prospective LOHC candidates, our study provides a valuable resource for researchers and engineers in the development of advanced LOHC systems and showcases a successful approach for high-throughput discovery, contributing to more efficient and sustainable energy storage solutions.

Research Organization:
Argonne National Laboratory (ANL), Argonne, IL (United States)
Sponsoring Organization:
USDOE Laboratory Directed Research and Development (LDRD) Program; USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities (SUF)
Grant/Contract Number:
AC02-06CH11357
OSTI ID:
2009005
Alternate ID(s):
OSTI ID: 2477600
Journal Information:
Digital Discovery, Vol. 2, Issue 6; ISSN 2635-098X
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (93)

Role of Liquid Hydrogen Carriers in Deeply Decarbonized Energy Systems journal August 2022
Liquid Organic Hydrogen Carriers: High-throughput Screening of Homogeneous Catalysts preprint February 2023
The Generation of a Unique Machine Description for Chemical Structures-A Technique Developed at Chemical Abstracts Service. journal May 1965
The effect of temperature, catalyst and sterics on the rate of N-heterocycledehydrogenation for hydrogenstorage journal January 2011
A benchmark study of aromaticity indexes for benzene, pyridine and the diazines – I. Ground state aromaticity journal January 2022
Storage of Hydrogen in Reversible Aromatic Organic Liquids book March 2023
Estimation of synthetic accessibility score of drug-like molecules based on molecular complexity and fragment contributions journal June 2009
Machine Learning in Catalysis, From Proposal to Practicing journal December 2019
The Prospect of Hydrogen Storage Using Liquid Organic Hydrogen Carriers journal March 2019
UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations journal December 1992
Aromatic liquid organic hydrogen carriers for hydrogen storage and release journal August 2023
Reinforcement learning supercharges redox flow batteries journal August 2022
A prototype truck powered by hydrogen from organic liquid hydrides journal January 1985
Nanocrystallites-forming hierarchical porous Ni/Al2O3–TiO2 catalyst for dehydrogenation of organic chemical hydrides journal October 2011
Language-oriented rule-based reaction network generation and analysis: Description of RING journal October 2012
The Selective Hydrogenation of Derivatives of Pyrrole, Indole, Carbazole and Acridine journal June 1941
Language-oriented rule-based reaction network generation and analysis: Applications of RING journal November 2012
Reversible ammonia-based and liquid organic hydrogen carriers for high-density hydrogen storage: Recent progress journal March 2019
Efficient hydrogen supply through catalytic dehydrogenation of methylcyclohexane over Pt/metal oxide catalysts journal May 2010
Direct synthesis of formic acid from carbon dioxide by hydrogenation in acidic media journal June 2014
Liquid Organic Hydrogen Carriers (LOHCs): Toward a Hydrogen-free Hydrogen Economy journal December 2016
Dehydrogenation of Dodecahydro- N -ethylcarbazole on Pt(111) journal May 2013
A systematic review on green hydrogen for off-grid communities –technologies, advantages, and limitations journal June 2023
Thermochemical Properties and Dehydrogenation Thermodynamics of Indole Derivates journal November 2020
Reversible storage and release of hydrogen with LOHC: Evaluation of thermochemical data for methyl-quinolines with complementary experimental and computational methods journal June 2022
Recent Advances in Carbon Dioxide Hydrogenation to Methanol via Heterogeneous Catalysis journal February 2020
Colmena: Scalable Machine-Learning-Based Steering of Ensemble Simulations for High Performance Computing conference November 2021
Language-oriented rule-based reaction network generation and analysis: Algorithms of RING journal May 2014
Homogeneously-catalysed hydrogen release/storage using the 2-methylindole/2-methylindoline LOHC system in molten salt-organic biphasic reaction systems journal January 2019
Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions journal May 1992
Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions journal January 1980
Development of dehydrogenation catalyst for hydrogen generation in organic chemical hydride method journal August 2006
Novel CO 2 Electrochemical Reduction to Methanol for H 2 Storage journal January 2004
Critical challenges towards the commercial rollouts of a LOHC-based H2 economy journal June 2023
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals journal July 2007
Hydrogen-storage materials for mobile applications book October 2010
Hydrogenation and dehydrogenation reactions of benzofuran and its derivatives (review) journal April 1976
Environmental and health impact assessment of Liquid Organic Hydrogen Carrier (LOHC) systems – challenges and preliminary results journal January 2015
OPERA models for predicting physicochemical properties and environmental fate endpoints journal March 2018
Parsl: Pervasive Parallel Programming in Python
  • Babuji, Yadu; Foster, Ian; Wilde, Michael
  • Proceedings of the 28th International Symposium on High-Performance Parallel and Distributed Computing - HPDC '19 https://doi.org/10.1145/3307681.3325400
conference January 2019
Liquid organic hydrogen carriers journal September 2015
Hydrogen storage book January 2022
Liquid Organic Hydrogen Carriers and alternatives for international transport of renewable hydrogen journal January 2021
Advances and prospects in electrocatalytic hydrogenation of aromatic hydrocarbons for synthesis of “loaded” liquid organic hydrogen carriers journal April 2023
Energy storage in residential and commercial buildings via Liquid Organic Hydrogen Carriers (LOHC) journal January 2012
A future energy supply based on Liquid Organic Hydrogen Carriers (LOHC) journal January 2011
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections journal January 2008
Liquid Organic Hydrogen Carriers as an efficient vector for the transport and storage of renewable energy journal December 2012
Temperature controlled three-stage catalytic dehydrogenation and cycle performance of perhydro-9-ethylcarbazole journal September 2012
Homogeneous Transition Metal Catalysis of Acceptorless Dehydrogenative Alcohol Oxidation: Applications in Hydrogen Storage and to Heterocycle Synthesis journal January 2017
Lower Temperature Dehydrogenation of Methylcyclohexane by Membrane-assisted Equilibrium Shift journal December 2006
Thirty years of density functional theory in computational chemistry: an overview and extensive assessment of 200 density functionals journal April 2017
The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage journal January 2008
Prediction of organic homolytic bond dissociation enthalpies at near chemical accuracy with sub-second computational cost journal May 2020
Inverse molecular design using machine learning: Generative models for matter engineering journal July 2018
ZINC 15 – Ligand Discovery for Everyone journal November 2015
Ab Initio Machine Learning in Chemical Compound Space journal August 2021
Liquid Organic Hydrogen Carriers (LOHCs) as H‐Source for Bio‐Derived Fuels and Additives Production journal March 2022
Big Data Meets Quantum Chemistry Approximations: The Δ-Machine Learning Approach journal April 2015
Best‐Practice DFT Protocols for Basic Molecular Computational Chemistry** journal September 2022
Toward a Hydrogen Economy: Development of Heterogeneous Catalysts for Chemical Hydrogen Storage and Release Reactions journal October 2022
Accelerating Communications in Federated Applications with Transparent Object Proxies preprint January 2023
Nitrogen-Containing Liquid Organic Hydrogen Carriers: Progress and Prospects journal May 2017
Off-board regeneration of ammonia borane for use as a hydrogen carrier for automotive fuel cells journal October 2012
Machine learning–assisted molecular design and efficiency prediction for high-performance organic photovoltaic materials journal November 2019
Global Methodology for Catalyst Screening and Optimization Process. Application to Mild Hydrocracking journal November 2020
Enumeration of 166 Billion Organic Small Molecules in the Chemical Universe Database GDB-17 journal November 2012
Targeting and scheduling of standalone renewable energy system with liquid organic hydrogen carrier as energy storage journal March 2021
Hazard assessment of quinaldine-, alkylcarbazole-, benzene- and toluene-based liquid organic hydrogen carrier (LOHCs) systems journal January 2019
Quantum-Chemically Informed Machine Learning: Prediction of Energies of Organic Molecules with 10 to 14 Non-hydrogen Atoms journal June 2020
A modified steam-methane-reformation reaction for hydrogen production journal April 2011
Computational structure–activity relationships in H 2 storage: how placement of N atoms affects release temperatures in organic liquid storage materials journal January 2007
Hydrogen storage by liquid organic hydrogen carriers: Catalyst, renewable carrier, and technology – A review journal December 2023
Potential Liquid-Organic Hydrogen Carrier (LOHC) Systems: A Review on Recent Progress journal November 2020
Performance of Similarity Measures in 2D Fragment-Based Similarity Searching:  Comparison of Structural Descriptors and Similarity Coefficients journal November 2002
A Review of Catalysts for Methylcyclohexane Dehydrogenation journal July 2021
Self‐consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets journal April 1984
Liquid organic hydrogen carriers for transportation and storing of renewable energy – Review and discussion journal August 2018
Efficient evolution of hydrogen from liquid cycloalkanes over Pt-containing catalysts supported on active carbons under “wet–dry multiphase conditions” journal July 2002
Finding minima, transition states, and following reaction pathways on ab initio potential energy surfaces book January 2005
Melting Points of Potential Liquid Organic Hydrogen Carrier Systems Consisting of N-Alkylcarbazoles journal March 2016
A computational workflow to discover novel liquid organic hydrogen carriers and their dehydrogenation routes journal January 2020
Liquid Organic Hydrogen Carrier (LOHC) – Assessment based on chemical and economic properties journal March 2019
Liquid organic hydrogen carriers (LOHCs) – techno-economic analysis of LOHCs in a defined process chain journal January 2019
Why is Tanimoto index an appropriate choice for fingerprint-based similarity calculations? journal May 2015
Homogeneous Catalytic System for Reversible Dehydrogenation−Hydrogenation Reactions of Nitrogen Heterocycles with Reversible Interconversion of Catalytic Species journal June 2009
Catalytic Generation of Hydrogen from Formic acid and its Derivatives: Useful Hydrogen Storage Materials journal May 2010
Deep Learning in Chemistry journal May 2019
Machine learning for molecular and materials science journal July 2018
Hydrogen storage in liquid organic heterocycles journal January 2008
Autonomous Chemical Experiments: Challenges and Perspectives on Establishing a Self-Driving Lab journal August 2022
Chemical hydrides: A solution to high capacity hydrogen storage and supply journal January 2008
Hydrogen liquefaction and storage: Recent progress and perspectives journal April 2023