HCCSCCCCSCC(TIPS)

What is HCCSCCCCSCC(TIPS)

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Preparation Process: To prepare HCCSCCCCSCC(TIPS), follow these steps: 1. **Protection**: Start with propargyl alcohol (HC≡CCH₂OH) and protect the hydroxyl group with TIPS-Cl (triisopropylsilyl chloride) in the presence of imidazole/DMF to yield HC≡CCH₂OTIPS. 2. **Thiolation**: Treat HC≡CCH₂OTIPS with NaSH in methanol to form HSCH₂C≡CCH₂OTIPS. 3. **Alkylation**: React HSCH₂C≡CCH₂OTIPS with 1,4-dibromobutane (Br(CH₂)₄Br) and K₂CO₃ in acetone to yield HS(CH₂)₄C≡CCH₂OTIPS. 4. **Final Coupling**: Combine HS(CH₂)₄C≡CCH₂OTIPS with bromoacetylene (HC≡CBr) and K₂CO₃ in acetone to obtain HCCSCCCCSCC(TIPS). Purify by column chromatography.

Usage Scenarios: The compound HCCSCCCCSCC(TIPS) is a thiol-terminated organic molecule with a triisopropylsilyl (TIPS) protecting group. It is primarily used in organic synthesis, particularly in the formation of self-assembled monolayers (SAMs) on gold and other metal surfaces for applications in nanotechnology and surface chemistry. The TIPS group enhances stability and prevents unwanted reactions during synthesis. The thiol groups enable strong binding to metal surfaces, making it useful in molecular electronics, biosensors, and catalysis. Additionally, it serves as a precursor in the synthesis of more complex organic and organometallic compounds, aiding in controlled polymerization and functional material design.

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