[{"OA_type":"closed access","month":"07","_id":"21816","extern":"1","quality_controlled":"1","publication":"ACS Applied Materials & Interfaces","abstract":[{"text":"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.","lang":"eng"}],"article_type":"original","date_published":"2021-07-26T00:00:00Z","citation":{"ista":"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.","short":"S.J. Bailey, F.J. Stricker, E. Hopkins, M.Z. Wilson, J. Read de Alaniz, ACS Applied Materials &#38; Interfaces 13 (2021) 35422–35430.","mla":"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>.","chicago":"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>.","ama":"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>","ieee":"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.","apa":"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>"},"doi":"10.1021/acsami.1c08670","publication_identifier":{"issn":["1944-8244"],"eissn":["1944-8252"]},"scopus_import":"1","type":"journal_article","publication_status":"published","fulldoi":"https://doi.org/10.1021/acsami.1c08670","intvolume":"        13","day":"26","external_id":{"pmid":["34310127"]},"issue":"30","oa_version":"None","ddc":["540"],"article_processing_charge":"No","title":"Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced click chemistry with cyclopentadiene","pmid":1,"date_created":"2026-05-06T10:54:16Z","publisher":"American Chemical Society","user_id":"ba8df636-2132-11f1-aed0-ed93e2281fdd","year":"2021","author":[{"first_name":"Sophia J.","last_name":"Bailey","full_name":"Bailey, Sophia J."},{"id":"7aca2cfc-46cf-11f0-abd3-8c96b5186745","full_name":"Stricker, Friedrich J","last_name":"Stricker","first_name":"Friedrich J"},{"last_name":"Hopkins","full_name":"Hopkins, Erik","first_name":"Erik"},{"first_name":"Maxwell Z.","full_name":"Wilson, Maxwell Z.","last_name":"Wilson"},{"first_name":"Javier","last_name":"Read de Alaniz","full_name":"Read de Alaniz, Javier"}],"status":"public","volume":13,"language":[{"iso":"eng"}],"keyword":["click chemistry","Diels−Alder","cyclopentadiene","photochemistry","photopatterning"],"date_updated":"2026-05-12T09:49:57Z","page":"35422-35430"}]