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Improved model for fullerene C60 solubility in organic solvents based on quantum-chemical and topological descriptors

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Abstract

Fullerenes are sparingly soluble in many solvents. The dependence of fullerene’s solubility on molecular structure of the solvent must be understood in order to manage efficiently this class of compounds. To find such dependency ab initio quantum-chemical calculations in combination with quantitative structure–property relationship (QSPR) tool were used to model the solubility of fullerene C60 in 122 organic solvents. A genetic algorithm and multiple regression analysis (GA-MLRA) were applied to generate correlation models. The best performance is accomplished by the four-variable MLRA model with prediction coefficient r 2test  = 0.903. This study reveals a correlation of highest occupied molecular orbital energy (HOMO), certain heteroatom fragments, and geometrical parameters with solubility. Several other important parameters of solvents that affect the C60 solubility have been also evaluated by the QSPR analysis. The employed GA-MLRA approach enhanced by application of quantum-chemical calculations yields reliable results, allowing one to build simple, interpretable models that can be used for predictions of C60 solubility in various organic solvents.

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Acknowledgments

The authors would like to thank for support the National Science Foundation for the “Interdisciplinary Center for Nanotoxicity” support—NSF HRD #0833178; for NSF EPSCoR Grant no. 362492-190200-01\NSFEPS-0903787 and Department of Defense through the U. S. Army Engineer Research and Development Center (Vicksburg, MS) for the grant “Development of Predictive Techniques for Modeling Properties of NanoMaterials Using New OSPR/QSAR Approach Based on Optimal NanoDescriptors”—Contract #W912HZ-06-C-0061. The authors are grateful to the Mississippi Center for Supercomputing Research (MCSR) for providing state-of-the-arts high performance computing facilities and excellent services for supporting this research.

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Authors and Affiliations

  1. Interdisciplinary Center for Nanotoxicity, Department of Chemistry and Biochemistry, Jackson State University, 1400 J. R. Lynch Street, P.O. Box 17910, Jackson, MS, 39217, USA

    Tetyana Petrova, Bakhtiyor F. Rasulev & Jerzy Leszczynski

  2. Istituto di Ricerche Farmacologiche Mario Negri, Via La Masa 19, 20156, Milano, Italy

    Andrey A. Toropov

  3. Department of Civil and Environmental Engineering, Jackson State University, 1400 J. R. Lynch Street, P.O. Box 17910, Jackson, MS, 39217, USA

    Danuta Leszczynska

Authors
  1. Tetyana Petrova
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  2. Bakhtiyor F. Rasulev
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  3. Andrey A. Toropov
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  4. Danuta Leszczynska
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  5. Jerzy Leszczynski
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Correspondence to Bakhtiyor F. Rasulev.

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Petrova, T., Rasulev, B.F., Toropov, A.A. et al. Improved model for fullerene C60 solubility in organic solvents based on quantum-chemical and topological descriptors. J Nanopart Res 13, 3235–3247 (2011). https://doi.org/10.1007/s11051-011-0238-x

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  • DOI: https://doi.org/10.1007/s11051-011-0238-x

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