Bioinspired Functional Catechol Derivatives Through Simple Thiol Conjugate Addition

MANCEBO-ARACIL, JUAN; CASAGUALDA, CAROLINA; MORENO-VILLAÉCIJA, MIGUEL ÁNGEL; NADOR, FABIANA GABRIELA; GARCÍA-PARDO, JAVIER; FRANCONETTI-GARCÍA, ANTONIO; BUSQUÉ, FÉLIX; ALIBÉS, RAMÓN; ESPLANDIU, MARÍA JOSÉ; RUIZ-MOLINA, DANIEL; SEDÓ-VEGARA, JOSEP

CHEMISTRY-A EUROPEAN JOURNAL

WILEY-V C H VERLAG GMBH

Año: 2019

0947-6539

The combination of the surface-adhesive properties ofcatechol rings and functional moieties conveying specific propertiesis very appealing to materials chemistry, but the preparation ofcatechol derivatives often requires elaborate synthetic routes tocircumvent the intrinsic reactivity of the catechol ring. In this work,functional catechols are synthesized straightforwardly using thebioinspired reaction of several functional thiols with o-benzoquinone.With one exception, the conjugated addition of the thiol takes placeregioselectively at the 3-position of the quinone, and is rationalizedby DFT calculations. Overall, this synthetic methodology is shown toprovide a general and straightforward access to functional andchain-extended catechol derivatives, which are later put to the testwith regard to their hydro/oleophobicity, colloidal stability,fluorescence and metal-coordinating capabilities in proof-of-conceptapplications.