1：Experimental Design and Method Selection:

The synthesis involved cross-condensation reactions between bulky phthalonitrile derivatives and imido-phthalonitriles to form trans-ABAB ZnPcs, followed by hydrolysis or deprotection to achieve amphiphilic derivatives. Photophysical studies included UV-Vis spectroscopy, fluorescence measurements, and direct observation of singlet oxygen phosphorescence.

2：Sample Selection and Data Sources:

Compounds 1a-g were synthesized and purified using column chromatography. Solvents like THF and toluene were used for photophysical measurements.

3：List of Experimental Equipment and Materials:

Equipment included microwave reactors (Biotage Initiator+), NMR spectrometers (Bruker AC-300 and XRD-500), UV-Vis spectrophotometer (JASCO-V660), IR spectrophotometer (Agilent Technologies Cary 630 FTIR), and mass spectrometers (VG-AutoSpec and Bruker Reflex III). Materials included silica gel for chromatography, various phthalonitrile derivatives, and solvents.

4：Experimental Procedures and Operational Workflow:

Synthesis steps involved cross-condensation, purification, and deprotection. Photophysical measurements were conducted at various concentrations to study aggregation and singlet oxygen generation.

5：Data Analysis Methods:

Linear regression for Lambert-Beer law verification, monoexponential decay kinetics for fluorescence, and quantification of singlet oxygen quantum yields using direct phosphorescence observation.