Combined Computational Approach Based on Density Functional Theory and Artificial Neural Networks for Predicting The Solubility Parameters of Fullerenes.

The solubility of organic semiconductors in environmentally benign solvents is an important prerequisite for the widespread adoption of organic electronic appliances. Solubility can be determined by considering the cohesive forces in a liquid via Hansen solubility parameters (HSP). We report a numerical approach to determine the HSP of fullerenes using a mathematical tool based on artificial neural networks (ANN). ANN transforms the molecular surface charge density distribution (σ-profile) as determined by density functional theory (DFT) calculations within the framework of a continuum solvation model into solubility parameters. We validate our model with experimentally determined HSP of the fullerenes C60, PC61BM, bisPC61BM, ICMA, ICBA, and PC71BM and through comparison with previously reported molecular dynamics calculations. Most excitingly, the ANN is able to correctly predict the dispersive contributions to the solubility parameters of the fullerenes although no explicit information on the van der Waals forces is present in the σ-profile. The presented theoretical DFT calculation in combination with the ANN mathematical tool can be easily extended to other π-conjugated, electronic material classes and offers a fast and reliable toolbox for future pathways that may include the design of green ink formulations for solution-processed optoelectronic devices.

[1]  M. Toney,et al.  Effect of Solvent Additives on the Solution Aggregation of Phenyl-C61–Butyl Acid Methyl Ester (PCBM) , 2015 .

[2]  Chi C Hua,et al.  Solubility of C60 and PCBM in Organic Solvents. , 2015, The journal of physical chemistry. B.

[3]  Paul Heremans,et al.  Determination of Solvent Systems for Blade Coating Thin Film Photovoltaics , 2015 .

[4]  A. Hexemer,et al.  The Crystallization of PEDOT:PSS Polymeric Electrodes Probed In Situ during Printing , 2015, Advanced materials.

[5]  R. Dauskardt,et al.  Molecular-Scale Understanding of Cohesion and Fracture in P3HT:Fullerene Blends. , 2015, ACS applied materials & interfaces.

[6]  C. Brabec,et al.  Classification of additives for organic photovoltaic devices. , 2015, Chemphyschem : a European journal of chemical physics and physical chemistry.

[7]  R. J. Kline,et al.  In Situ Characterization of Polymer–Fullerene Bilayer Stability , 2015 .

[8]  Tyler B Fleetham,et al.  Development of non-halogenated binary solvent systems for high performance bulk-heterojunction organic solar cells , 2015 .

[9]  J. Brédas,et al.  Influence of Molecular Shape on Solid-State Packing in Disordered PC61BM and PC71BM Fullerenes. , 2014, The journal of physical chemistry letters.

[10]  J. Aubry,et al.  Hansen approach versus COSMO-RS for predicting the solubility of an organic UV filter in cosmetic solvents , 2014 .

[11]  E. Voutsas,et al.  Evaluation of COSMO-RS model in binary and ternary mixtures of natural antioxidants, ionic liquids and organic solvents , 2014 .

[12]  Christoph J. Brabec,et al.  Solubility Based Identification of Green Solvents for Small Molecule Organic Solar Cells , 2014 .

[13]  Hans-Joachim Egelhaaf,et al.  The Effect of PCBM Dimerization on the Performance of Bulk Heterojunction Solar Cells , 2014 .

[14]  S. Mehraeen,et al.  Materials‐Scale Implications of Solvent and Temperature on [6,6]‐Phenyl‐C61‐butyric Acid Methyl Ester (PCBM): A Theoretical Perspective , 2013 .

[15]  Thuc‐Quyen Nguyen,et al.  Molecular solubility and hansen solubility parameters for the analysis of phase separation in bulk heterojunctions , 2012 .

[16]  M. Toney,et al.  Factors Governing Intercalation of Fullerenes and Other Small Molecules Between the Side Chains of Semiconducting Polymers Used in Solar Cells , 2012 .

[17]  Steven Abbott,et al.  Determination of the P3HT:PCBM solubility parameters via a binary solvent gradient method: Impact of solubility on the photovoltaic performance , 2012 .

[18]  G. Járvás,et al.  Estimation of Hansen solubility parameters using multivariate nonlinear QSPR modeling with COSMO scr , 2011 .

[19]  J. Anthony.  Small-Molecule, Nonfullerene Acceptors for Polymer Bulk Heterojunction Organic Photovoltaics† , 2011 .

[20]  Yongfang Li,et al.  6.5% Efficiency of Polymer Solar Cells Based on poly(3‐hexylthiophene) and Indene‐C60 Bisadduct by Device Optimization , 2010, Advanced materials.

[21]  A. Klamt,et al.  COSMO-RS: an alternative to simulation for calculating thermodynamic properties of liquid mixtures. , 2010, Annual review of chemical and biomolecular engineering.

[22]  Emmanuel Stefanis,et al.  Prediction of Hansen Solubility Parameters with a New Group-Contribution Method , 2008 .

[23]  Stephen R. Forrest,et al.  The path to ubiquitous and low-cost organic electronic appliances on plastic , 2004, Nature.

[24]  C. Hansen,et al.  Using Hansen solubility parameters to correlate solubility of C60 fullerene in organic solvents and in polymers , 2004 .

[25]  Michael L. Michelsen,et al.  A Flory–Huggins model based on the Hansen solubility parameters , 2002 .

[26]  Andreas Klamt,et al.  Use of COSMO‐RS for the prediction of adsorption equilibria , 2002 .

[27]  Yizhak Marcus,et al.  Solubility of C60 Fullerene , 2001 .

[28]  A. Klamt.  Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena , 1995 .