The combination of the surface-adhesive properties of catechol rings and functional moieties conveyings pecific properties is very appealing to materials chemistry,b ut the preparation of catechol derivatives often requires elaborate synthetic routes to circumventt he intrinsic reactivity of the catechol ring. In this work, functional catechols are synthesized straightforwardly by using the bioinspired reaction of several functionalt hiols with o-benzoquinone. With one exception,t he conjugated addition of the thiol takes place regioselectively at the 3-positiono ft he quinone, and is rationalized by DFT calculations. Overall, this synthetic methodology provides ag eneral and straightforward access to functional andc hain-extended catechold erivatives, which are later tested with regard to their hydro-/oleophobicity, colloidal stability, fluorescence, and metal-coordinatingc apabilities in proof-of-concept applications.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

The control of surface wettability with polyphenol coatings has been at the forefront of materials research since the late 1990s, when robust underwater adhesion was linked to the presence of L-DOPA—a catecholic amino acid—in unusually high amounts, in the sequences of several mussel foot proteins. Since then, several successful approaches have been reported, although a common undesired feature of most of them is the presence of a remnant color and/or the intrinsic difficulty in fine-tuning and controlling the hydrophobic character. We report here a new family of functional catechol-based coatings, grounded in the oxidative condensation of readily available pyrocatechol and thiol-capped functional moieties. The presence of at least two additional thiol groups in their structure allows for polymerization through the formation of disulfide bonds. The synthetic flexibility, together with its modular character, allowed us to: (I) develop coatings with applications exemplified by textiles for oil-spill water treatment; (II) develop multifunctional coatings, and (III) fine-tune the WCA for flat and textile surfaces. All of this was achieved with the application of colorless coatings.

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