In the design of fluorescence and bioluminescence probes, it is common to attach electron-donating groups (EDG) and electron-withdrawing groups (EWG) to a fluorophore to adjust its frontier orbital energies and thus the absorption/emission wavelengths.   To help understand such substituent effects, we will present a new procedure for analyzing the interactions between fluorophore orbitals and substituent orbitals (Chem. Sci. 2018, 10.1039/C8SC02990C).  Using prodan and oxyluciferin as examples, we will show different effects, especially permanent electrostatics and orbital mixing, can play key roles in the modulation of the fluorophore frontier orbitals.  <br/>

Computational modeling of substituent effect on the frontier orbitals of conjugated molecules

2019 Spring National Meeting

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