Click and Bioorthogonal Chemistry for the Creation of Dynamic Materials

Venue: Seminar room, via Sommarive 9, Department of Industrial Engineering, Povo - Trento - h: 3:00 pm

• Pierangelo Gobbo, NSERC & EU Marie Curie Fellow, School of Chemistry, The University of Bristol, UK

Recent years have seen the development of dynamic materials whose physical-chemical properties can be turned on and off when desired. However, the development of dynamic materials capable of chemoselective recognition still represents a challenge in the field. The achievement of such material systems will represent an important scientific and technological advancement, but it requires the development of new synthetic strategies and new characterization methodologies to enable their interfacial chemistry to be investigated.

In this presentation it will be shown that by introducing click and bioorthogonal groups at the interface of materials it is possible to make them to react chemoselectively even in complex media. These click and bioorthogonal groups include a maleimide that can undergo Michael-type addition or cycloaddition reactions with different functional groups, strained alkynes for bioorthogonal strain-promoted cycloaddition reactions with azides or nitrones, and methyl-2-(diphenylphosphino)benzoate moieties for the bioorthogonal Staudinger-Bertozzi ligation with azides.

In order to study and characterize these clickable and bioorthogonal materials, methodologies for the determination of the amount of reactive functionalities introduced onto the material’s surface and the evaluation of their proper reactivity were also developed. In particular, NMR spectroscopy and X-ray photoelectron spectroscopy were pivotal to 1) quantitate the amount of interfacial reactive molecules that were introduced, 2) track the interfacial organic chemistry of the nanomaterial template, and 3) determine interfacial reaction yields.

In all cases the clickable and bioorthogonal materials were found to react quickly, efficiently and chemoselectively with their corresponding reaction partners through a simple “pour-and-mix” type of chemistry. The utility of these clickable and bioorthogonal materials will be finally showcased in bioconjugation, for the synthesis of fluorogenic biosensors, nanomaterial hybrids and nanomaterial-based MRI contrast agents and in the emerging field of protolife science.

Contacts:
prof. Sandra Dirè
Materials Chemistry Group & "Klaus Mueller" NMR Laboratory
0461 28 2456 - sandra.dire [at] unitn.it