Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced click chemistry with cyclopentadiene Bailey, Sophia J. Stricker, Friedrich J Hopkins, Erik Wilson, Maxwell Z. Read de Alaniz, Javier click chemistry Diels−Alder cyclopentadiene photochemistry photopatterning ddc:540 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. American Chemical Society 2021 info:eu-repo/semantics/article doc-type:Article Article http://purl.org/coar/resource_type/c_2df8fbb1 https://research-explorer.ista.ac.at/record/21816 Bailey SJ, Stricker FJ, Hopkins E, Wilson MZ, Read de Alaniz J. Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced click chemistry with cyclopentadiene. <i>ACS Applied Materials &#38; Interfaces</i>. 2021;13(30):35422-35430. doi:<a href="https://doi.org/10.1021/acsami.1c08670">10.1021/acsami.1c08670</a> eng info:eu-repo/semantics/altIdentifier/doi/10.1021/acsami.1c08670 info:eu-repo/semantics/altIdentifier/issn/1944-8244 info:eu-repo/semantics/altIdentifier/e-issn/1944-8252 info:eu-repo/semantics/altIdentifier/pmid/34310127 info:eu-repo/semantics/closedAccess