A Bayesian Approach to Predict Solubility Parameters

Sanchez‐Lengeling, Benjamin; Roch, Loïc M.; Perea, José Darío; Langner, Stefan; Brabec, Christoph J.; Aspuru‐Guzik, Alán

doi:10.1002/adts.201800069

Title: A Bayesian Approach to Predict Solubility Parameters

Journal Article · 10 September 2018 · Advanced Theory and Simulations

DOI: https://doi.org/10.1002/adts.201800069 · OSTI ID:1469250

^[1];

^[1]; Perea, José Darío ^[2]; Langner, Stefan ^[2]; Brabec, Christoph J. ^[3];

^[4]

Department of Chemistry and Chemical Biology Harvard University Cambridge MA 02138 USA
Institute of Materials for Electronics and Energy Technology (i-MEET) Friedrich‐Alexander‐Universität Erlangen‐Nürnberg Martensstrasse 7 91058 Erlangen Germany
Institute of Materials for Electronics and Energy Technology (i-MEET) Friedrich‐Alexander‐Universität Erlangen‐Nürnberg Martensstrasse 7 91058 Erlangen Germany, Bavarian Center for Applied Energy Research (ZAE Bayern) Immerwahrstrasse 2 91058 Erlangen Germany
Department of Chemistry and Chemical Biology Harvard University Cambridge MA 02138 USA, Canadian Institute for Advanced Research Toronto Ontario M5G 1Z8 Canada, Department of Computer Science University of Toronto Toronto Ontario M5S 3H7 Canada

Abstract Solubility is a ubiquitous phenomenon in many aspects of material science. While solubility can be determined by considering the cohesive forces in a liquid via the Hansen solubility parameters (HSP), quantitative structure–property relationship models are often used for prediction, notably due to their low computational cost. Here, gpHSP, an interpretable and versatile probabilistic approach to determining HSP, is reported. Our model is based on Gaussian processes, a Bayesian machine learning approach that provides uncertainty bounds to prediction. gpHSP achieves its flexibility by leveraging a variety of input data, such as SMILES strings, COSMOtherm simulations, and quantum chemistry calculations. gpHSP is built on experimentally determined HSP, including a general solvents set aggregated from the literature, and a polymer set experimentally characterized by this group of authors. In all sets, a high degree of agreement is obtained, surpassing well‐established machine learning methods. The general applicability of gpHSP to miscibility of organic semiconductors, drug compounds, and in general solvents is demonstrated, which can be further extended to other domains. gpHSP is a fast and accurate toolbox, which could be applied to molecular design for solution processing technologies.

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Sponsoring Organization:: USDOE

OSTI ID:: 1469250

Journal Information:: Advanced Theory and Simulations, Journal Name: Advanced Theory and Simulations Journal Issue: 1 Vol. 2; ISSN 2513-0390

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (58)

Solubility Based Identification of Green Solvents for Small Molecule Organic Solar Cells Burgués-Ceballos, Ignasi; Machui, Florian; Min, Jie Advanced Functional Materials, Vol. 24, Issue 10 https://doi.org/10.1002/adfm.201301509	journal	November 2013
For the Bright Future-Bulk Heterojunction Polymer Solar Cells with Power Conversion Efficiency of 7.4% Liang, Yongye; Xu, Zheng; Xia, Jiangbin Advanced Materials, Vol. 22, Issue 20, p. E135-E138 https://doi.org/10.1002/adma.200903528	journal	May 2010
A Systematic Approach to Solvent Selection Based on Cohesive Energy Densities in a Molecular Bulk Heterojunction System Walker, Bright; Tamayo, Arnold; Duong, Duc T. Advanced Energy Materials, Vol. 1, Issue 2 https://doi.org/10.1002/aenm.201000054	journal	February 2011
Guiding the Selection of Processing Additives for Increasing the Efficiency of Bulk Heterojunction Polymeric Solar Cells Vongsaysy, Uyxing; Pavageau, Bertrand; Wantz, Guillaume Advanced Energy Materials, Vol. 4, Issue 3 https://doi.org/10.1002/aenm.201300752	journal	September 2013
Small is Powerful: Recent Progress in Solution-Processed Small Molecule Solar Cells Collins, Samuel D.; Ran, Niva A.; Heiber, Michael C. Advanced Energy Materials, Vol. 7, Issue 10 https://doi.org/10.1002/aenm.201602242	journal	January 2017
Miscibility-Function Relations in Organic Solar Cells: Significance of Optimal Miscibility in Relation to Percolation Ye, Long; Collins, Brian A.; Jiao, Xuechen Advanced Energy Materials, Vol. 8, Issue 28 https://doi.org/10.1002/aenm.201703058	journal	January 2018
Generalizing solubility parameter theory to apply to one- and two-dimensional solutes and to incorporate dipolar interactions Hughes, J. Marguerite; Aherne, Damian; Coleman, Jonathan N. Journal of Applied Polymer Science, Vol. 127, Issue 6 https://doi.org/10.1002/app.38051	journal	June 2012
Modeling of Hansen's solubility parameters of aripiprazole, ziprasidone, and their impurities: A nonparametric comparison of models for prediction of drug absorption sites: Linear and nonlinear modeling of Hansen's solubility parameters Obradović, Darija; Andrić, Filip; Zlatović, Mario Journal of Chemometrics, Vol. 32, Issue 4 https://doi.org/10.1002/cem.2996	journal	January 2018
Classification of Additives for Organic Photovoltaic Devices Machui, Florian; Maisch, Philipp; Burgués-Ceballos, Ignasi ChemPhysChem, Vol. 16, Issue 6 https://doi.org/10.1002/cphc.201402734	journal	January 2015
Semiempirical GGA-type density functional constructed with a long-range dispersion correction Grimme, Stefan Journal of Computational Chemistry, Vol. 27, Issue 15, p. 1787-1799 https://doi.org/10.1002/jcc.20495	journal	January 2006
Optimization and application of lithium parameters for PM3 Anders, Ernst; Koch, Rainer; Freunscht, Peter Journal of Computational Chemistry, Vol. 14, Issue 11 https://doi.org/10.1002/jcc.540141106	journal	November 1993
Determination of Solubility Parameters for Organic Semiconductor Formulations Machui, Florian; Abbott, Steven; Waller, David Macromolecular Chemistry and Physics, Vol. 212, Issue 19 https://doi.org/10.1002/macp.201100284	journal	August 2011
Application of QSPR to Binary Polymer/Solvent Mixtures: Prediction of Flory-Huggins Parameters Xu, Jie; Liu, Hongtao; Li, Wenbin Macromolecular Theory and Simulations, Vol. 17, Issue 9 https://doi.org/10.1002/mats.200800063	journal	December 2008
Molecular solubility and hansen solubility parameters for the analysis of phase separation in bulk heterojunctions Duong, Duc T.; Walker, Bright; Lin, Jason Journal of Polymer Science Part B: Polymer Physics, Vol. 50, Issue 20 https://doi.org/10.1002/polb.23153	journal	August 2012
The ORCA program system: The ORCA program system Neese, Frank Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 1 https://doi.org/10.1002/wcms.81	journal	June 2011
Fast Parallel Algorithms for Short-Range Molecular Dynamics Plimpton, Steve Journal of Computational Physics, Vol. 117, Issue 1 https://doi.org/10.1006/jcph.1995.1039	journal	March 1995
Optimization of parameters for semiempirical methods VI: more modifications to the NDDO approximations and re-optimization of parameters Stewart, James J. P. Journal of Molecular Modeling, Vol. 19, Issue 1 https://doi.org/10.1007/s00894-012-1667-x	journal	November 2012
Computational Prediction of Drug Solubility in Fasted Simulated and Aspirated Human Intestinal Fluid Fagerberg, Jonas H.; Karlsson, Eva; Ulander, Johan Pharmaceutical Research, Vol. 32, Issue 2 https://doi.org/10.1007/s11095-014-1487-z	journal	September 2014
Cocrystal Solubility Product Prediction Using an in combo Model and Simulations to Improve Design of Experiments Avdeef, Alex Pharmaceutical Research, Vol. 35, Issue 2 https://doi.org/10.1007/s11095-018-2343-3	journal	February 2018
Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings 1PII of original article: S0169-409X(96)00423-1. The article was originally published in Advanced Drug Delivery Reviews 23 (1997) 3–25. 1 Lipinski, Christopher A.; Lombardo, Franco; Dominy, Beryl W. Advanced Drug Delivery Reviews, Vol. 46, Issue 1-3 https://doi.org/10.1016/S0169-409X(00)00129-0	journal	March 2001
Determination of partial solubility parameters of five benzodiazepines in individual solvents Verheyen, S.; Augustijns, P.; Kinget, R. International Journal of Pharmaceutics, Vol. 228, Issue 1-2 https://doi.org/10.1016/S0378-5173(01)00838-9	journal	October 2001
The use of solubility parameters in pharmaceutical dosage form design Hancock, B. International Journal of Pharmaceutics, Vol. 148, Issue 1 https://doi.org/10.1016/S0378-5173(96)04828-4	journal	March 1997
The modified extended Hansen method to determine partial solubility parameters of drugs containing a single hydrogen bonding group and their sodium derivatives: benzoic acid/Na and ibuprofen/Na Bustamante, P.; Peña, M. A.; Barra, J. International Journal of Pharmaceutics, Vol. 194, Issue 1 https://doi.org/10.1016/S0378-5173(99)00374-9	journal	January 2000
Solubility parameter and oral absorption Martini, Luigi G.; Avontuur, Paul; George, Ashley European Journal of Pharmaceutics and Biopharmaceutics, Vol. 48, Issue 3 https://doi.org/10.1016/S0939-6411(99)00055-7	journal	November 1999
Application of Hansen Solubility Parameters to predict drug–nail interactions, which can assist the design of nail medicines Hossin, B.; Rizi, K.; Murdan, S. European Journal of Pharmaceutics and Biopharmaceutics, Vol. 102 https://doi.org/10.1016/j.ejpb.2016.02.009	journal	May 2016
Estimation of Hansen solubility parameters using multivariate nonlinear QSPR modeling with COSMO screening charge density moments Járvás, Gábor; Quellet, Christian; Dallos, András Fluid Phase Equilibria, Vol. 309, Issue 1 https://doi.org/10.1016/j.fluid.2011.06.030	journal	October 2011
Hansen solubility parameter as a tool to predict cocrystal formation Mohammad, Mohammad Amin; Alhalaweh, Amjad; Velaga, Sitaram P. International Journal of Pharmaceutics, Vol. 407, Issue 1-2 https://doi.org/10.1016/j.ijpharm.2011.01.030	journal	April 2011
The role of miscibility in polymer:fullerene nanoparticulate organic photovoltaic devices Ulum, Syahrul; Holmes, Natalie; Barr, Matthew Nano Energy, Vol. 2, Issue 5 https://doi.org/10.1016/j.nanoen.2013.03.009	journal	September 2013
Determination of the P3HT:PCBM solubility parameters via a binary solvent gradient method: Impact of solubility on the photovoltaic performance Machui, Florian; Langner, Stefan; Zhu, Xiangdong Solar Energy Materials and Solar Cells, Vol. 100 https://doi.org/10.1016/j.solmat.2012.01.005	journal	May 2012
MultiDK: A Multiple Descriptor Multiple Kernel Approach for Molecular Discovery and Its Application to Organic Flow Battery Electrolytes Kim, Sungjin; Jinich, Adrián; Aspuru-Guzik, Alán Journal of Chemical Information and Modeling, Vol. 57, Issue 4 https://doi.org/10.1021/acs.jcim.6b00332	journal	April 2017
A Simple Representation of Three-Dimensional Molecular Structure Axen, Seth D.; Huang, Xi-Ping; Cáceres, Elena L. Journal of Medicinal Chemistry, Vol. 60, Issue 17 https://doi.org/10.1021/acs.jmedchem.7b00696	journal	August 2017
Combined Computational Approach Based on Density Functional Theory and Artificial Neural Networks for Predicting The Solubility Parameters of Fullerenes Perea, J. Darío; Langner, Stefan; Salvador, Michael The Journal of Physical Chemistry B, Vol. 120, Issue 19 https://doi.org/10.1021/acs.jpcb.6b00787	journal	May 2016
Introducing a New Potential Figure of Merit for Evaluating Microstructure Stability in Photovoltaic Polymer-Fullerene Blends Perea, José Darío; Langner, Stefan; Salvador, Michael The Journal of Physical Chemistry C, Vol. 121, Issue 33 https://doi.org/10.1021/acs.jpcc.7b03228	journal	August 2017
Molecular-Scale Understanding of Cohesion and Fracture in P3HT:Fullerene Blends Tummala, Naga Rajesh; Bruner, Christopher; Risko, Chad ACS Applied Materials & Interfaces, Vol. 7, Issue 18 https://doi.org/10.1021/acsami.5b02202	journal	April 2015
Suppression of Thermally Induced Fullerene Aggregation in Polyfullerene-Based Multiacceptor Organic Solar Cells Dowland, Simon A.; Salvador, Michael; Perea, José Darío ACS Applied Materials & Interfaces, Vol. 9, Issue 12 https://doi.org/10.1021/acsami.7b00401	journal	March 2017
Extended-Connectivity Fingerprints Rogers, David; Hahn, Mathew Journal of Chemical Information and Modeling, Vol. 50, Issue 5 https://doi.org/10.1021/ci100050t	journal	April 2010
Solubility Challenge: Can You Predict Solubilities of 32 Molecules Using a Database of 100 Reliable Measurements? Llinàs, Antonio; Glen, Robert C.; Goodman, Jonathan M. Journal of Chemical Information and Modeling, Vol. 48, Issue 7 https://doi.org/10.1021/ci800058v	journal	June 2008
Sigma-Profile Database for Using COSMO-Based Thermodynamic Methods Mullins, Eric; Oldland, Richard; Liu, Y. A. Industrial & Engineering Chemistry Research, Vol. 45, Issue 12 https://doi.org/10.1021/ie060370h	journal	June 2006
UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations Rappe, A. K.; Casewit, C. J.; Colwell, K. S. Journal of the American Chemical Society, Vol. 114, Issue 25, p. 10024-10035 https://doi.org/10.1021/ja00051a040	journal	December 1992
DFTB+, a Sparse Matrix-Based Implementation of the DFTB Method ^† Aradi, B.; Hourahine, B.; Frauenheim, Th. The Journal of Physical Chemistry A, Vol. 111, Issue 26 https://doi.org/10.1021/jp070186p	journal	July 2007
Influence of Molecular Shape on Solid-State Packing in Disordered PC ₆₁ BM and PC ₇₁ BM Fullerenes Williams, Monika; Tummala, Naga Rajesh; Aziz, Saadullah G. The Journal of Physical Chemistry Letters, Vol. 5, Issue 19 https://doi.org/10.1021/jz501559q	journal	September 2014
Polymer Crystallization of Partially Miscible Polythiophene/Fullerene Mixtures Controls Morphology Kozub, Derek R.; Vakhshouri, Kiarash; Orme, Lisa M. Macromolecules, Vol. 44, Issue 14 https://doi.org/10.1021/ma200855r	journal	July 2011
Determination of Solvent–Polymer and Polymer–Polymer Flory–Huggins Interaction Parameters for Poly(3-hexylthiophene) via Solvent Vapor Swelling Emerson, Jillian A.; Toolan, Daniel T. W.; Howse, Jonathan R. Macromolecules, Vol. 46, Issue 16 https://doi.org/10.1021/ma400597j	journal	August 2013
In Situ Characterization of Polymer–Fullerene Bilayer Stability Leman, Deborah; Kelly, Mary Allison; Ness, Stuart Macromolecules, Vol. 48, Issue 2 https://doi.org/10.1021/ma5021227	journal	January 2015
Block Copolymers for Organic Optoelectronics Segalman, Rachel A.; McCulloch, Bryan; Kirmayer, Saar Macromolecules, Vol. 42, Issue 23 https://doi.org/10.1021/ma901350w	journal	December 2009
Multicomponent Solubility Parameters for Single-Walled Carbon Nanotube−Solvent Mixtures Bergin, Shane D.; Sun, Zhenyu; Rickard, David ACS Nano, Vol. 3, Issue 8 https://doi.org/10.1021/nn900493u	journal	August 2009
Abnormal strong burn-in degradation of highly efficient polymer solar cells caused by spinodal donor-acceptor demixing Li, Ning; Perea, José Darío; Kassar, Thaer Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms14541	journal	February 2017
Accelerating the discovery of materials for clean energy in the era of smart automation Tabor, Daniel P.; Roch, Loïc M.; Saikin, Semion K. Nature Reviews Materials, Vol. 3, Issue 5 https://doi.org/10.1038/s41578-018-0005-z	journal	April 2018
A review of methods for the calculation of solution free energies and the modelling of systems in solution Skyner, R. E.; McDonagh, J. L.; Groom, C. R. Physical Chemistry Chemical Physics, Vol. 17, Issue 9 https://doi.org/10.1039/C5CP00288E	journal	January 2015
Understanding the correlation and balance between the miscibility and optoelectronic properties of polymer–fullerene solar cells Zhang, Chaohong; Langner, Stefan; Mumyatov, Alexander V. Journal of Materials Chemistry A, Vol. 5, Issue 33 https://doi.org/10.1039/C7TA03505E	journal	January 2017
COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2, Issue 5 https://doi.org/10.1039/P29930000799	journal	January 1993
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy Weigend, Florian; Ahlrichs, Reinhart Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305 https://doi.org/10.1039/b508541a	journal	January 2005
Nanotube–polymer composites: insights from Flory–Huggins theory and mesoscale simulations Maiti, Amitesh; Wescott, James; Kung, Paul Molecular Simulation, Vol. 31, Issue 2-3 https://doi.org/10.1080/08927020412331308539	journal	February 2005
PubChem Substance and Compound databases Kim, Sunghwan; Thiessen, Paul A.; Bolton, Evan E. Nucleic Acids Research, Vol. 44, Issue D1 https://doi.org/10.1093/nar/gkv951	journal	September 2015
Density-functional exchange-energy approximation with correct asymptotic behavior Becke, A. D. Physical Review A, Vol. 38, Issue 6 https://doi.org/10.1103/PhysRevA.38.3098	journal	September 1988
Density-functional approximation for the correlation energy of the inhomogeneous electron gas Perdew, John P. Physical Review B, Vol. 33, Issue 12 https://doi.org/10.1103/PhysRevB.33.8822	journal	June 1986
Learning Nonlinear Functions Using Regularized Greedy Forest Johnson, Rie; Zhang, Tong IEEE Transactions on Pattern Analysis and Machine Intelligence, Vol. 36, Issue 5 https://doi.org/10.1109/TPAMI.2013.159	journal	May 2014
ChemOS: Orchestrating autonomous experimentation Roch, Loïc M.; Häse, Florian; Kreisbeck, Christoph Science Robotics, Vol. 3, Issue 19 https://doi.org/10.1126/scirobotics.aat5559	journal	June 2018

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