Selectively activated crosslinkers for sequential functionalization of polymers
Date
2025
Authors
Tupper, Eillie
Musolino, Stefania F.
Wulff, Jeremy E.
Journal Title
Journal ISSN
Volume Title
Publisher
University Of Victoria
Abstract
Previous work by the Wulff group has investigated several polymer crosslinkers containing two identical diazirine moieties (Science, 2019). The diazirine group is excited by photocuring or thermal activation, releasing nitrogen and generating a carbene, which allows for the C-H, O-H, or N-H insertion of a polymer. This was expanded upon in later work by the Wulff group, where it was found that changing the electronics of each diazirine allows them to be activated using different wavelengths of light (Chemical Science, 2021).
A new molecule, DualLynx (2nd Gen), DL-2, was created using one diazirine with an electron-donating group and one with an electron-withdrawing group. The difference in electronics between the two reactive groups allows the diazirines to be activated sequentially, a unique feature for bis-diazirine crosslinkers.
This project demonstrates the unique properties of the DL-2 molecule through a series of small-molecule experiments in solution. While preliminary polymer experiments indicate that the structure of DL-2 may not be optimized for surface functionalization, investigation of the dimerized side product formed in this reaction gives some insight into the behaviour and reactivity of the diazirine motif.
Description
Keywords
organic chemistry, polymer, diazirine, rosslinker