Polymeric self-assembled monolayers .4. Chemical, electrochemical, and thermal stability of omega-functionalized, self-assembled diacetylenic and polydiacetylenic monolayers

Here we contrast the stability of monomeric and photopolymerized self-assembled monolayers (SAMs) containing a diacetylene group (HS(CH2)(10)C=CC=C(CH2)(10)COOH) with SAMs prepared from simple n-alkanethiols. The polymerized SAMs are;extremely durable compared to either the n-alkanethiol SAMs or the unpolymerized diacetylenic SAMs. For example, they are stable to repeated electrochemical cycling to extreme potentials, thermal excursions to 200 degrees C, and exposure to hot base (1:1 mixture of ethanol and 1.0 M aqueous KOH at 100 degrees C). All of these conditions completely strip n-alkanethiol SAMs from Au substrates. These high-performance materials are suitable for applications in lubrication, adhesion, corrosion passivation, and chemical sensing.