Synthesis of New Functionalized Cyclopentadienes To Reach Reversible Bonding between Two Substrates

Siffer, Frédéric; Roucoules, Vincent; Vallat, Marie‐France; Defoin, Albert

doi:10.1055/s-2008-1032158

Cited by 1 publication

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References 14 publications

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“…The well-known Diels-Alder (DA) and retro Diels-Alder (retro DA) chemistry has been widely used in the design of stimuli-responsive interfaces. Examples concern mainly applications in adhesion [1,2], and in the controlled immobilization and release of molecules [3,4]. The unique thermoreversible character of this reaction allows the formation (Diels-Alder reaction) and dissociation (retro Diels-Alder reaction) of an adduct with a simple change of temperature and without any side reactions [5].…”

Section: Introductionmentioning

confidence: 99%

Using TOF-SIMS Spectrometry to Study the Kinetics of the Interfacial Retro Diels–Alder Reaction

et al. 2021

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In this work, the use of Time of Flight Secondary Ion Mass Spectrometry (TOF-SIMS) was explored as a technique for monitoring the interfacial retro Diels–Alder (retro DA) reaction occurring on well-controlled self-assembled monolayers (SAMs). A molecule containing a Diels–Alder (DA) adduct was grafted on to the monolayers, then the surface was heated at different temperatures to follow the reaction conversion. A TOF-SIMS analysis of the surface allowed the detection of a fragment from the molecule, which is released from the surface when retro DA reaction occurs. Hence, by monitoring the decay of this fragment’s peak integral, the reaction conversion could be determined in function of the time and for different temperatures. The viability of this method was then discussed in comparison with the results obtained by 1H NMR spectroscopy.

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