1：Experimental Design and Method Selection:

The study involved synthesizing twelve meso-phenyl-BODIPY compounds with 0 to 3 methoxy groups to act as donor-acceptor entities. Photophysical properties (UV-Vis absorption, fluorescence emission, quantum yields, lifetimes) and singlet oxygen generation were measured. DFT quantum chemical computations were used to explain experimental results.

2：Sample Selection and Data Sources:

Compounds were synthesized using aldehydes and 2,4-dimethylpyrrole, with characterization via NMR, HRMS, and UV-Vis spectra. Solvents of varying polarities (n-hexane, ethyl acetate, THF, pinacolone, acetone, methanol, acetonitrile) were used for measurements.

3：List of Experimental Equipment and Materials:

Chemicals from Sigma-Aldrich, Acros Organics, Merck, or Fluka; solvents dried and redistilled; silica gel for chromatography; Bruker dmx NMR spectrometer (600 MHz for 1H, 75 MHz for 13C); LTQ Orbitrap XL TOF spectrometer for mass spectra; Vary 8454 spectrometer for UV-Vis absorption; FLS 920 Fluorescence Spectrometer for fluorescence measurements; laser flash photolysis setup for triplet state identification; Gaussian 09 package for DFT computations.

4：Experimental Procedures and Operational Workflow:

Synthesis via one-pot reaction with aldehydes and 2,4-dimethylpyrrole in dichloromethane, addition of trifluoroacetic acid, 2,3-dicyano-5,6-dichlorobenzoquinone, N,N-Diisopropylethylamine, and boron trifluoride etherate, followed by purification. Photophysical measurements included absorption and fluorescence spectra, quantum yields using comparative method with fluorescein reference, lifetimes via TCSPC, singlet oxygen quantum yields using DPBF chemical trapping with 8-methylthio-2,6-diiodoBODIPY reference, and laser flash photolysis for triplet state.

5：Data Analysis Methods:

Fluorescence quantum yields calculated using comparative equation; singlet oxygen quantum yields calculated based on DPBF photobleaching kinetics; DFT computations with B3LYP functional and 6-311G basis set, including solvent effects via CPCM model.