1：Experimental Design and Method Selection:

The study involved synthesizing novel phthalonitrile derivatives and their phthalocyanine complexes, followed by spectroscopic characterization and investigation of photophysical and photochemical properties. Theoretical models for aggregation behavior and photochemical mechanisms (e.g., Type II for singlet oxygen generation) were employed.

2：Sample Selection and Data Sources:

Samples included synthesized compounds 1-6, with characterization using elemental analysis, UV-Vis spectrophotometry, FT-IR spectrometry, 1H-NMR spectroscopy, and mass spectrometry. Data were acquired from laboratory experiments.

3：List of Experimental Equipment and Materials:

Equipment included spectrophotometers, spectrometers, and mass spectrometers (e.g., MALDI-TOF). Materials included phthalonitrile derivatives, metal salts (e.g., Zn(CH3COO)2, InCl3), solvents (e.g., THF, DMSO), and reagents (e.g., DPBF for singlet oxygen detection).

4：Experimental Procedures and Operational Workflow:

Synthesis involved nucleophilic substitution reactions with K2CO3 in DMSO at 50°C, followed by cyclotetramerization with DBU in n-hexanol at 160°C. Characterization steps included purification via column chromatography and spectral measurements. Photophysical studies involved dilution tests in THF to check aggregation, and photochemical studies measured fluorescence quantum yields, singlet oxygen quantum yields using DPBF, and photodegradation quantum yields under light irradiation.

5：Data Analysis Methods:

Data were analyzed using linear regression for Lambert-Beer law compliance, comparative analysis of quantum yields, and statistical evaluation of spectral data.