Abstract
The derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) are pivotal ingredients for a large number of functional, stimuli-responsive materials and therapeutic molecules based on their photophysical properties, and there is a urgent need to understand and predict their optical traits prior to investing a large amount of resources in preparing them. Density functional theory (DFT) and time-dependent DFT (TDDFT) computations were performed to calculate the excitation energies of the lowest-energy singlet excited state of a large series of common BODIPY derivatives employing various functional aiming at the best possible combination providing the least deviations from the experimental values. Using the common “fudge” correction, a series of combinations was investigated, and a methodology is proposed offering equal or better performances than what is reported in the literature.
Highlights
The BODIPY pigment and its derivatives are key entities for phototheranostics [1], including photodynamic therapy [2], functional optoelectronic materials [3], such as solar cells [4,5,6] and light emitting diodes [7], and stimuli-responsive materials [8,9,10,11]
Ab initio calculations were reported with good results, but the computational time is an unneglectable parameter to consider [47,48]
Most of the BODIPY core are planar or quasi planar with small deviation up to 30 degree in extreme cases. This issue has already been addressed by Orte and coworkers [27] and, in our case, did not explicitly interfere with the TD-Density functional theory (DFT) calculations for the estimation of the 0-0 transition
Summary
The BODIPY pigment and its derivatives are key entities for phototheranostics [1], including photodynamic therapy [2], functional optoelectronic materials [3], such as solar cells [4,5,6] and light emitting diodes [7], and stimuli-responsive materials [8,9,10,11]. Ab initio calculations were reported with good results, but the computational time is an unneglectable parameter to consider [47,48]. From all these previous investigations, the main conclusion is that the methodology that requires the least resources in material science and biomedical research is the application of an empirical correction: “fudge” [18,38,49]. Fudge methods generally consist in applying an empirical correction to calculated data to make them fit with experimental results This method is used for TD-DFT computations where the shape of the simulated spectra compare favorably with the experiments but exhibit large offsets in terms of wavelength position
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