@article{21816,
  abstract     = {A new Diels−Alder (DA)-based photopatterning platform is presented, which exploits the irreversible, light-induced decarbonylation and subsequent cleavage of cyclopentadienone−norbornadiene (CPD−NBD) adducts. A series of CPD−NBD adducts have been prepared and systematically studied toward the use in a polymeric material photopatterning platform. By incorporating an optimized CPD−NBD adduct into polymer networks, it is demonstrated that cyclopentadiene may be unveiled upon 365 nm irradiation and subsequently clicked to a variety of maleimides with spatial control under mild reaction conditions and with fast kinetics. Unlike currently available photoinduced Diels−Alder reactions that rely on trapping transient, photocaged dienes, this platform introduces a persistent, yet highly reactive diene after irradiation, enabling the use of photosensitive species such as cyanine dyes to be patterned. To highlight the potential use of this platform in a variety of material applications, we demonstrate two proof-of-concepts: patterned conjugation of multiple dyes into apolyacrylate network and preprogrammed ligation of streptavidin into poly(ethylene glycol) hydrogels.},
  author       = {Bailey, Sophia J. and Stricker, Friedrich J and Hopkins, Erik and Wilson, Maxwell Z. and Read de Alaniz, Javier},
  issn         = {1944-8252},
  journal      = {ACS Applied Materials & Interfaces},
  keywords     = {click chemistry, Diels−Alder, cyclopentadiene, photochemistry, photopatterning},
  number       = {30},
  pages        = {35422--35430},
  publisher    = {American Chemical Society},
  title        = {{Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced click chemistry with cyclopentadiene}},
  doi          = {10.1021/acsami.1c08670},
  volume       = {13},
  year         = {2021},
}