[{"article_processing_charge":"No","title":"Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","year":"2021","page":"10219-10227","volume":60,"pmid":1,"oa_version":"Published Version","date_published":"2021-04-26T00:00:00Z","external_id":{"pmid":["33503292"]},"ddc":["540"],"author":[{"last_name":"Clerc","first_name":"Michèle","full_name":"Clerc, Michèle"},{"first_name":"Friedrich J","full_name":"Stricker, Friedrich J","last_name":"Stricker","id":"7aca2cfc-46cf-11f0-abd3-8c96b5186745"},{"last_name":"Ulrich","full_name":"Ulrich, Sebastian","first_name":"Sebastian"},{"first_name":"Miranda","full_name":"Sroda, Miranda","last_name":"Sroda"},{"first_name":"Nico","full_name":"Bruns, Nico","last_name":"Bruns"},{"first_name":"Luciano F.","full_name":"Boesel, Luciano F.","last_name":"Boesel"},{"last_name":"Read de Alaniz","full_name":"Read de Alaniz, Javier","first_name":"Javier"}],"month":"04","intvolume":"        60","publication_identifier":{"issnl":["1433-7851"],"issn":["1521-3773"]},"main_file_link":[{"url":"https://doi.org/10.1002/anie.202100115","open_access":"1"}],"publisher":"Wiley","OA_place":"publisher","publication":"Angewandte Chemie International Edition","status":"public","day":"26","article_type":"original","doi":"10.1002/anie.202100115","type":"journal_article","tmp":{"short":"CC BY (4.0)","name":"Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)","legal_code_url":"https://creativecommons.org/licenses/by/4.0/legalcode","image":"/images/cc_by.png"},"date_created":"2026-05-06T10:42:50Z","publication_status":"published","_id":"21805","issue":"18","extern":"1","date_updated":"2026-05-11T07:40:12Z","quality_controlled":"1","citation":{"short":"M. Clerc, F.J. Stricker, S. Ulrich, M. Sroda, N. Bruns, L.F. Boesel, J. Read de Alaniz, Angewandte Chemie International Edition 60 (2021) 10219–10227.","chicago":"Clerc, Michèle, Friedrich J Stricker, Sebastian Ulrich, Miranda Sroda, Nico Bruns, Luciano F. Boesel, and Javier Read de Alaniz. “Promoting the Furan Ring‐opening Reaction to Access New Donor-Acceptor Stenhouse Adducts with Hexafluoroisopropanol.” <i>Angewandte Chemie International Edition</i>. Wiley, 2021. <a href=\"https://doi.org/10.1002/anie.202100115\">https://doi.org/10.1002/anie.202100115</a>.","ieee":"M. Clerc <i>et al.</i>, “Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol,” <i>Angewandte Chemie International Edition</i>, vol. 60, no. 18. Wiley, pp. 10219–10227, 2021.","mla":"Clerc, Michèle, et al. “Promoting the Furan Ring‐opening Reaction to Access New Donor-Acceptor Stenhouse Adducts with Hexafluoroisopropanol.” <i>Angewandte Chemie International Edition</i>, vol. 60, no. 18, Wiley, 2021, pp. 10219–27, doi:<a href=\"https://doi.org/10.1002/anie.202100115\">10.1002/anie.202100115</a>.","ama":"Clerc M, Stricker FJ, Ulrich S, et al. Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol. <i>Angewandte Chemie International Edition</i>. 2021;60(18):10219-10227. doi:<a href=\"https://doi.org/10.1002/anie.202100115\">10.1002/anie.202100115</a>","apa":"Clerc, M., Stricker, F. J., Ulrich, S., Sroda, M., Bruns, N., Boesel, L. F., &#38; Read de Alaniz, J. (2021). Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol. <i>Angewandte Chemie International Edition</i>. Wiley. <a href=\"https://doi.org/10.1002/anie.202100115\">https://doi.org/10.1002/anie.202100115</a>","ista":"Clerc M, Stricker FJ, Ulrich S, Sroda M, Bruns N, Boesel LF, Read de Alaniz J. 2021. Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol. Angewandte Chemie International Edition. 60(18), 10219–10227."},"language":[{"iso":"eng"}],"oa":1,"abstract":[{"lang":"eng","text":"Donor–acceptor Stenhouse adducts (DASAs) are visible‐light‐responsive photoswitches with a variety of emerging applications in photoresponsive materials. Their two‐step modular synthesis, centered on the nucleophilic ring opening of an activated furan, makes DASAs readily accessible. However, the use of less reactive donors or acceptors renders the process slow and low yielding, which has limited their development. We demonstrate here that 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) promotes the ring‐opening reaction and stabilizes the open isomer, allowing greatly reduced reaction times and increased yields for known derivatives. In addition, it provides access to previously unattainable DASA‐based photoswitches and DASA–polymer conjugates. The role of HFIP and the photochromic properties of a set of new DASAs is probed using a combination of <jats:sup>1</jats:sup>H NMR and UV/Vis spectroscopy. The use of sterically hindered, electron‐poor amines enabled the dark equilibrium to be decoupled from closed‐isomer half‐lives for the first time."}],"scopus_import":"1","OA_type":"hybrid"},{"publisher":"Wiley","language":[{"iso":"eng"}],"abstract":[{"lang":"eng","text":"Hydrogen bonds are ubiquitous interactions in proteins, and are important for their folding and functionality. Scalar coupling constants across hydrogen bonds in the protein backbone, some as small as 0.5 Hz, can be directly measured in the solid state by NMR spectroscopy (see figure). The nuclei on both sides of the hydrogen bond can be identified and the size of the coupling constant can be measured accurately."}],"publication":"Angewandte Chemie International Edition","status":"public","keyword":["General Chemistry","Catalysis"],"month":"11","intvolume":"        48","issue":"49","_id":"8474","extern":"1","publication_identifier":{"issn":["1433-7851","1521-3773"]},"citation":{"mla":"Schanda, Paul, et al. “Direct Detection of 3hJN’ Hydrogen-Bond Scalar Couplings in Proteins by Solid-State NMR Spectroscopy.” <i>Angewandte Chemie International Edition</i>, vol. 48, no. 49, Wiley, 2009, pp. 9322–25, doi:<a href=\"https://doi.org/10.1002/anie.200904411\">10.1002/anie.200904411</a>.","ieee":"P. Schanda, M. Huber, R. Verel, M. Ernst, and B. Meier, “Direct detection of 3hJN’ hydrogen-bond scalar couplings in proteins by solid-state NMR spectroscopy,” <i>Angewandte Chemie International Edition</i>, vol. 48, no. 49. Wiley, pp. 9322–9325, 2009.","chicago":"Schanda, Paul, Matthias Huber, René Verel, Matthias Ernst, and Beat H. Meier. “Direct Detection of 3hJN’ Hydrogen-Bond Scalar Couplings in Proteins by Solid-State NMR Spectroscopy.” <i>Angewandte Chemie International Edition</i>. Wiley, 2009. <a href=\"https://doi.org/10.1002/anie.200904411\">https://doi.org/10.1002/anie.200904411</a>.","short":"P. Schanda, M. Huber, R. Verel, M. Ernst, B. Meier, Angewandte Chemie International Edition 48 (2009) 9322–9325.","ista":"Schanda P, Huber M, Verel R, Ernst M, Meier B. 2009. Direct detection of 3hJN’ hydrogen-bond scalar couplings in proteins by solid-state NMR spectroscopy. Angewandte Chemie International Edition. 48(49), 9322–9325.","apa":"Schanda, P., Huber, M., Verel, R., Ernst, M., &#38; Meier, B. (2009). Direct detection of 3hJN’ hydrogen-bond scalar couplings in proteins by solid-state NMR spectroscopy. <i>Angewandte Chemie International Edition</i>. Wiley. <a href=\"https://doi.org/10.1002/anie.200904411\">https://doi.org/10.1002/anie.200904411</a>","ama":"Schanda P, Huber M, Verel R, Ernst M, Meier B. Direct detection of 3hJN’ hydrogen-bond scalar couplings in proteins by solid-state NMR spectroscopy. <i>Angewandte Chemie International Edition</i>. 2009;48(49):9322-9325. doi:<a href=\"https://doi.org/10.1002/anie.200904411\">10.1002/anie.200904411</a>"},"quality_controlled":"1","date_updated":"2021-01-12T08:19:31Z","doi":"10.1002/anie.200904411","type":"journal_article","author":[{"full_name":"Schanda, Paul","first_name":"Paul","last_name":"Schanda","id":"7B541462-FAF6-11E9-A490-E8DFE5697425","orcid":"0000-0002-9350-7606"},{"last_name":"Huber","full_name":"Huber, Matthias","first_name":"Matthias"},{"full_name":"Verel, René","first_name":"René","last_name":"Verel"},{"full_name":"Ernst, Matthias","first_name":"Matthias","last_name":"Ernst"},{"last_name":"Meier","full_name":"Meier, Beat H.","first_name":"Beat H."}],"publication_status":"published","date_created":"2020-09-18T10:11:33Z","article_processing_charge":"No","day":"17","title":"Direct detection of 3hJN' hydrogen-bond scalar couplings in proteins by solid-state NMR spectroscopy","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","year":"2009","page":"9322-9325","oa_version":"None","date_published":"2009-11-17T00:00:00Z","article_type":"original","volume":48}]