1：Experimental Design and Method Selection:

The synthesis of compound 1 involved a multi-step process starting from 3,3’,5,5’-tetrabromo-2,2’-bithiophene, including iodination, Ullmann-type coupling with TipCu, selective debromination, and lithiation followed by addition of dichlorosilane. Characterization methods included NMR, IR, mass spectroscopy, X-ray crystallography, UV/Vis spectroscopy, fluorescence spectroscopy, and theoretical calculations (TD-DFT). The reaction with Pt(PPh3)2(C2H4) was performed to study complexation.

2：Sample Selection and Data Sources:

Compounds 1 and 7 were synthesized and characterized. Reference compounds II and related siloles were used for comparison. Data were obtained from synthesized samples and theoretical models.

3：List of Experimental Equipment and Materials:

NMR spectrometers (JEOL JNM-LA500, JNM-ECA600), IR spectrophotometer (Shimadzu FTIR-8700), mass spectrometers (JEOL JMS-SX102, Bruker Daltonics solariX), UV/Vis spectrophotometer (JASCO V-570), spectrofluorometer (Hitachi F-4500), absolute PL quantum yield measurement system (Hamamatsu Photonics C9920-02), lifetime fluorometer (Horiba Jobin Yvon FluoroCube 3000U), microwave synthesizer (Biotage Initiator), X-ray diffractometer (Rigaku R-AXIS IV++), computational software (Gaussian 09). Chemicals included 3,3’,5,5’-tetrabromo-2,2’-bithiophene, TipCu, dichlorosilane, Pt(PPh3)2(C2H4), solvents (THF, diethyl ether, toluene, benzene, chloroform, hexane), and reagents (iodine, orthoperiodic acid, butyllithium, etc.).

4：9). Chemicals included 3,3’,5,5’-tetrabromo-2,2’-bithiophene, TipCu, dichlorosilane, Pt(PPh3)2(C2H4), solvents (THF, diethyl ether, toluene, benzene, chloroform, hexane), and reagents (iodine, orthoperiodic acid, butyllithium, etc.). Experimental Procedures and Operational Workflow:

4. Experimental Procedures and Operational Workflow: Synthesis steps: iodination of 3,3’,5,5’-tetrabromo-2,2’-bithiophene to 2; Ullmann coupling with TipCu under microwave irradiation to 3; selective debromination with butyllithium to 4; lithiation and reaction with dichlorosilane to

5：Complexation:

reaction of 1 with Pt(PPh3)2(C2H4) in benzene to

6：Characterization:

NMR, IR, mass spectra, X-ray crystallography, UV/Vis, fluorescence measurements, quantum yield and lifetime determinations. Theoretical calculations: geometry optimization and TD-DFT at B3LYP level with various basis sets.

7：Data Analysis Methods:

NMR data analysis for structural elucidation, IR for functional groups, mass spectra for molecular weight, X-ray for crystal structure, UV/Vis for absorption properties, fluorescence for emission properties, quantum yields and lifetimes calculated using standard equations, theoretical data analyzed for electronic transitions and molecular orbitals.