1：Experimental Design and Method Selection:

The study involved synthesizing and characterizing four o-carboranyl compounds (CB1, CB2, CB1B, CB2B) based on 2-phenylpyridine and 2-(benzo[b]thiophen-2-yl)pyridine, with o-carborane introduced at the C4 position. Methods included Sonogashira and Suzuki-Miyaura coupling reactions, borylation, and photophysical measurements. Theoretical calculations using DFT and TD-DFT were employed to analyze electronic transitions.

2：Sample Selection and Data Sources:

Compounds were synthesized from commercially available reagents. Single crystals of CB2 and CB2B were grown for X-ray diffraction analysis. UV-vis and PL measurements were performed in degassed toluene solutions and PMMA films.

3：List of Experimental Equipment and Materials:

Instruments included Bruker Avance 400 NMR spectrometer, Jasco V-530 UV-vis spectrophotometer, Horiba FluoroMax-4P spectrophotometer, Edinburgh Instruments FLS920 spectrometer for lifetime measurements, and Bruker D8 QUEST CCD diffractometer for X-ray crystallography. Materials included various chemicals like decaborane, boronic acids, solvents (toluene, THF, etc.), and PMMA.

4：Experimental Procedures and Operational Workflow:

Synthesis involved multiple steps: Sonogashira reaction to form intermediate 3, Suzuki-Miyaura coupling to form 1a and 2a, cage formation with decaborane to form CB1 and CB2, borylation with BBr3 and methylation with AlMe3 to form CB1B and CB2B. Photophysical measurements were conducted in solution at 298 K and 77 K, and in PMMA films at 298 K. X-ray crystallography and theoretical calculations (DFT/B3LYP/6-31G(d)) were performed.

5：2B. Photophysical measurements were conducted in solution at 298 K and 77 K, and in PMMA films at 298 K. X-ray crystallography and theoretical calculations (DFT/B3LYP/6-31G(d)) were performed. Data Analysis Methods:

5. Data Analysis Methods: NMR spectra were analyzed for structural confirmation. UV-vis and PL data were used to determine absorption and emission wavelengths, quantum yields, and decay constants. Theoretical calculations provided insights into electronic transitions and orbital contributions.