article published yes Sophia J. Bailey author Friedrich J Stricker author 7aca2cfc-46cf-11f0-abd3-8c96b5186745 Erik Hopkins author Maxwell Z. Wilson author Javier Read de Alaniz author 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 Society2021 eng click chemistryDiels−Aldercyclopentadienephotochemistryphotopatterning 1944-8244 1944-8252 3431012710.1021/acsami.1c08670 133035422-35430 yes Bailey, Sophia J., Friedrich J Stricker, Erik Hopkins, Maxwell Z. Wilson, and Javier Read de Alaniz. “Shining Light on Cyclopentadienone–Norbornadiene Diels-Alder Adducts to Enable Photoinduced Click Chemistry with Cyclopentadiene.” <i>ACS Applied Materials &#38; Interfaces</i>. American Chemical Society, 2021. <a href="https://doi.org/10.1021/acsami.1c08670">https://doi.org/10.1021/acsami.1c08670</a>. Bailey, Sophia J., et al. “Shining Light on Cyclopentadienone–Norbornadiene Diels-Alder Adducts to Enable Photoinduced Click Chemistry with Cyclopentadiene.” <i>ACS Applied Materials &#38; Interfaces</i>, vol. 13, no. 30, American Chemical Society, 2021, pp. 35422–30, doi:<a href="https://doi.org/10.1021/acsami.1c08670">10.1021/acsami.1c08670</a>. Bailey SJ, Stricker FJ, Hopkins E, Wilson MZ, Read de Alaniz J. 2021. Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced click chemistry with cyclopentadiene. ACS Applied Materials &#38; Interfaces. 13(30), 35422–35430. S.J. Bailey, F.J. Stricker, E. Hopkins, M.Z. Wilson, J. Read de Alaniz, ACS Applied Materials &#38; Interfaces 13 (2021) 35422–35430. S. J. Bailey, F. J. Stricker, E. Hopkins, M. Z. Wilson, and J. Read de Alaniz, “Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced click chemistry with cyclopentadiene,” <i>ACS Applied Materials &#38; Interfaces</i>, vol. 13, no. 30. American Chemical Society, pp. 35422–35430, 2021. Bailey, S. J., Stricker, F. J., Hopkins, E., Wilson, M. Z., &#38; Read de Alaniz, J. (2021). Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced click chemistry with cyclopentadiene. <i>ACS Applied Materials &#38; Interfaces</i>. American Chemical Society. <a href="https://doi.org/10.1021/acsami.1c08670">https://doi.org/10.1021/acsami.1c08670</a> 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> 218162026-05-06T10:54:16Z2026-05-12T09:49:57Z