Facile, Convenient Synthesis of Highly Pure ω-Ferrocenylalkanethiols as Probes for Self-Assembled Monolayer (SAM) on Gold Surface

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 167; no. 1; pp. 239 - 249
• Main Authors: Tazaki, Masato, Okada, Kenji, Yakata, Kenshi, Nakano, Koji, Sakai, Masashi, Yonemitsu, Tadashi
• Format: Journal Article
• Language: English
• Published: Taylor & Francis Group 01-01-2000
• Subjects: high purity synthesis; isothiuronium salt; LAH/AlCl; probe for self-assembled monolayer (SAM); reduction of acylferrocene; ω-ferrocenylalkanethiols
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426500008082402

High purity synthesis of ω-ferrocenylalkanethiols (Fc(CH
2
)
n
−SH, n=6, 8, 11) was developed for their use in self-assembled monolayers on gold surface. The method employs a separation and purification of isothiuronium salt 6 to improve the purity of final products 7. The use of hazardous mercury in the Clemmensen reduction of acylferrocene 4 to alkylferrocenes 5 is avoided by an alternative LAH/AlCl
3
reduction.