Large Variability and Complexity of Isothermal Solubility for a Series of Redox-Active Phenothiazines

Chemical structures and abbreviations of the phenothiazine (PT) derivatives examined in this study.

Scientific Achievement

Phenothiazine derivatives present a robust analysis system for experimental solubility determination in all states of charge. The QSPR models were only moderately successful in predicting solubility of an unknown PT compound. Modeling solubility of a fairly complex molecular set with only a few descriptors is difficult.

Significance and Impact

30 differently functionalized PT derivatives used to understand the impact of molecular structure and chemical environment on solubility as a function of state of charge. NMR method presented in the study can be used as a high-throughput technique providing opportunities for automated experiments to determine solubility. Examination of molecular descriptors selected by the QSPR models provide hints about the factors affecting solubility.

Research Details

  • Synthesized the neutral and charged forms of PT derivatives
  • Determined their solubility in all states of charge using NMR method
  • Examined solubility trends for these PT derivatives using QSPR models
  • Multiple linear regression models were used to correlate these properties starting with a large set of molecular descriptors. Final QSPR models included four-to-six molecular descriptors, which were used to rationalize the data

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DOI: 10.1039/D2MA00598K

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