当前位置: X-MOL 学术Langmuir › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Para-Fluoro-Thiol Reaction on Anchor Layers Grafted from an Aryldiazonium Salt: A Tool for Surface Functionalization with Thiols
Langmuir ( IF 3.9 ) Pub Date : 2021-09-14 , DOI: 10.1021/acs.langmuir.1c02012
Ting Wu 1 , Christopher M Fitchett 1 , Alison J Downard 1
Affiliation  

A new coupling reaction, the para-fluoro-thiol (PFT) reaction, activated by base at room temperature, is reported for carbon surface functionalization. 4-Nitrothiophenol (4-NTP) and (3-nitrobenzyl)mercaptan (3-NBM) were coupled to pentafluorophenyl (F5-Ph) anchor layers grafted from the aryldiazonium ion formed in situ. The relative yields of the PFT reactions, estimated from the electrochemical responses of coupled nitrophenyl (NP) and nitrobenzyl (NB) groups, depended on the nucleophilicity of the thiolate and the strength of the base. The highest surface concentration (4.6 × 10–10 mol cm–2) was obtained using 3-NBM in the presence of [Bu4N]OH; this concentration corresponds to the maximum that is typically achieved for other high-yielding coupling reactions at aryldiazonium ion anchor layers. The PFT reaction is expected to be applicable to the numerous thiol derivatives commonly restricted to self-assembled monolayer (SAM) formation at gold and other noble metals, thereby opening a simple new approach for interface design on carbon substrates. The strategy may also have advantages for modification of gold surfaces: the layer prepared by coupling 3-NBM to F5-Ph films on gold was found to be more stable to storage under ambient conditions than self-assembled monolayers of 3-NBM.

中文翻译:

芳基重氮盐接枝锚层上的对氟硫醇反应:硫醇表面功能化的工具

一种新的偶联反应,氟硫醇 (PFT) 反应,在室温下被碱激活,被报道用于碳表面功能化。4-硝基苯硫酚 (4-NTP) 和 (3-硝基苄基) 硫醇 (3-NBM) 与五氟苯基 (F 5 -Ph) 锚固层偶联,该锚固层从原位形成的芳基重氮离子接枝。根据偶联的硝基苯基 (NP) 和硝基苄基 (NB) 基团的电化学响应估计 PFT 反应的相对产率取决于硫醇盐的亲核性和碱的强度。最高表面浓度(4.6×10 -10摩尔厘米-2)中的溶液在存在使用3- NBM获得的[卜4N]OH; 该浓度对应于在芳基重氮离子锚定层的其他高产偶联反应通常达到的最大值。PFT 反应有望适用于通常仅限于在金和其他贵金属上形成自组装单层 (SAM) 的众多硫醇衍生物,从而为碳基底上的界面设计开辟了一种简单的新方法。该策略还具有修饰金表面的优势:发现通过将 3-NBM 与金上的F 5 -Ph 薄膜偶联制备的层在环境条件下比 3-NBM 的自组装单层更稳定储存。
更新日期:2021-09-28
down
wechat
bug