Beyond Woodward-Fieser Rules: Design Principles of Property-Oriented Chromophores Based on Explainable Deep Learning...

An adequate understanding of molecular structure-property relationships is important for developing new molecules with desired properties. Although deep learning optical spectroscopy (DLOS) has been successfully applied to predict the optical and photophysical properties of organic chromophores, how specific functional groups and solvents affect the optical properties is not clearly understood. Here, we employed an explainable DLOS method by applying the integrated gradients method to DLOS. The integrated gradients method allows us to obtain attributions, indicating how much the functional group contributes to the optical properties including the absorption wavelength and bandwidth, extinction coefficients, emission wavelength and bandwidth, photoluminescence quantum yield, and lifetime. The attributions of 54 functional groups and 9 solvent molecules to seven optical properties are quantified and can be used to estimate the optical properties of chromophores as in the Woodward-Fieser rule. Unlike the Woodward-Fieser rule for only the absorption wavelength, the attributions obtained in this work can be applied to estimate all seven optical properties, which makes a significant extension of the Woodward-Fieser rules. In addition, we demonstrated a strategy for utilizing the attributions in the design of molecules and in tuning the optical properties of the molecules. The design of molecular structures using attributions can revolutionize the development of optimal molecules.