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<titleInfo><title>Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol</title></titleInfo>


<note type="publicationStatus">published</note>


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<name type="personal">
  <namePart type="given">Michèle</namePart>
  <namePart type="family">Clerc</namePart>
  <role><roleTerm type="text">author</roleTerm> </role></name>
<name type="personal">
  <namePart type="given">Friedrich J</namePart>
  <namePart type="family">Stricker</namePart>
  <role><roleTerm type="text">author</roleTerm> </role><identifier type="local">7aca2cfc-46cf-11f0-abd3-8c96b5186745</identifier></name>
<name type="personal">
  <namePart type="given">Sebastian</namePart>
  <namePart type="family">Ulrich</namePart>
  <role><roleTerm type="text">author</roleTerm> </role></name>
<name type="personal">
  <namePart type="given">Miranda</namePart>
  <namePart type="family">Sroda</namePart>
  <role><roleTerm type="text">author</roleTerm> </role></name>
<name type="personal">
  <namePart type="given">Nico</namePart>
  <namePart type="family">Bruns</namePart>
  <role><roleTerm type="text">author</roleTerm> </role></name>
<name type="personal">
  <namePart type="given">Luciano F.</namePart>
  <namePart type="family">Boesel</namePart>
  <role><roleTerm type="text">author</roleTerm> </role></name>
<name type="personal">
  <namePart type="given">Javier</namePart>
  <namePart type="family">Read de Alaniz</namePart>
  <role><roleTerm type="text">author</roleTerm> </role></name>














<abstract lang="eng">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 &lt;jats:sup&gt;1&lt;/jats:sup&gt;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.</abstract>
<accessCondition type="use and reproduction">https://creativecommons.org/licenses/by/4.0/</accessCondition>
<originInfo><publisher>Wiley</publisher><dateIssued encoding="w3cdtf">2021</dateIssued>
</originInfo>
<language><languageTerm authority="iso639-2b" type="code">eng</languageTerm>
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<relatedItem type="host"><titleInfo><title>Angewandte Chemie International Edition</title></titleInfo>
  <identifier type="issn">1521-3773</identifier>
  <identifier type="MEDLINE">33503292</identifier><identifier type="doi">10.1002/anie.202100115</identifier>
<part><detail type="volume"><number>60</number></detail><detail type="issue"><number>18</number></detail><extent unit="pages">10219-10227</extent>
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<mla>Clerc, Michèle, et al. “Promoting the Furan Ring‐opening Reaction to Access New Donor-Acceptor Stenhouse Adducts with Hexafluoroisopropanol.” &lt;i&gt;Angewandte Chemie International Edition&lt;/i&gt;, vol. 60, no. 18, Wiley, 2021, pp. 10219–27, doi:&lt;a href=&quot;https://doi.org/10.1002/anie.202100115&quot;&gt;10.1002/anie.202100115&lt;/a&gt;.</mla>
<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.” &lt;i&gt;Angewandte Chemie International Edition&lt;/i&gt;. Wiley, 2021. &lt;a href=&quot;https://doi.org/10.1002/anie.202100115&quot;&gt;https://doi.org/10.1002/anie.202100115&lt;/a&gt;.</chicago>
<ieee>M. Clerc &lt;i&gt;et al.&lt;/i&gt;, “Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol,” &lt;i&gt;Angewandte Chemie International Edition&lt;/i&gt;, vol. 60, no. 18. Wiley, pp. 10219–10227, 2021.</ieee>
<apa>Clerc, M., Stricker, F. J., Ulrich, S., Sroda, M., Bruns, N., Boesel, L. F., &amp;#38; Read de Alaniz, J. (2021). Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol. &lt;i&gt;Angewandte Chemie International Edition&lt;/i&gt;. Wiley. &lt;a href=&quot;https://doi.org/10.1002/anie.202100115&quot;&gt;https://doi.org/10.1002/anie.202100115&lt;/a&gt;</apa>
<ama>Clerc M, Stricker FJ, Ulrich S, et al. Promoting the furan ring‐opening reaction to access new donor-acceptor Stenhouse adducts with hexafluoroisopropanol. &lt;i&gt;Angewandte Chemie International Edition&lt;/i&gt;. 2021;60(18):10219-10227. doi:&lt;a href=&quot;https://doi.org/10.1002/anie.202100115&quot;&gt;10.1002/anie.202100115&lt;/a&gt;</ama>
<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.</ista>
<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.</short>
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