{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T07:49:34Z","timestamp":1791618574125,"version":"4.3.4"},"reference-count":47,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"},{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    As visible light responsive molecular tools, hemiindigo photoswitches are attracting increasing research interest. The development of chiral hemiindigo derivatives could expand their application fields. We synthesized the first hemiindigo\u2010based glycoside and glycomacrocycle in a few steps through Click reaction. These compounds can be readily photoisomerized under visible light irradiation, with a high photoconversion yield and good fatigue resistance under anaerobic conditions. Compared to the acyclic derivatives, the glycomacrocyclic hemiindigo linked through\n                    <jats:italic>N<\/jats:italic>\n                    \u2010substitution on the indoxyl moiety displayed a constrained molecular geometry, significantly modifying the shape of the absorption band in the visible. The hemiindigo glycomacrocyle also exhibited more efficient\n                    <jats:italic>Z<\/jats:italic>\n                    \u21c4\n                    <jats:italic>E<\/jats:italic>\n                    photoisomerization compared to its acyclic counterpart, with a two\u2010fold increase of the photochromic quantum yield (0.34 for\n                    <jats:italic>\n                      \u03a6\n                      <jats:sub>Z<\/jats:sub>\n                    <\/jats:italic>\n                    <jats:sub>\u2192<\/jats:sub>\n                    <jats:italic>\n                      <jats:sub>E<\/jats:sub>\n                    <\/jats:italic>\n                    and 0.12 for\n                    <jats:italic>\n                      \u03a6\n                      <jats:sub>E<\/jats:sub>\n                    <\/jats:italic>\n                    <jats:sub>\u2192<\/jats:sub>\n                    <jats:italic>\n                      <jats:sub>Z<\/jats:sub>\n                    <\/jats:italic>\n                    ). These observed specific photophysical behaviors were rationalized using DFT and TD\u2010DFT calculations. The most twisted\n                    <jats:italic>E\u2010<\/jats:italic>\n                    macrocycle displayed chiroptical activity, allowing an on\u2010off chiroptical switching upon\n                    <jats:italic>Z<\/jats:italic>\n                    \u2192\n                    <jats:italic>E<\/jats:italic>\n                    \u2192\n                    <jats:italic>Z<\/jats:italic>\n                    photoisomerization. All of the investigated hemiindigo derivatives exhibited fluorescence in their\n                    <jats:italic>Z<\/jats:italic>\n                    \u2010form.\n                  <\/jats:p>","DOI":"10.1002\/chem.71764","type":"journal-article","created":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T07:32:27Z","timestamp":1791185547000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and Characterization of Hemiindigo\u2010Based Glycoside and Glycomacrocycle"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-8219-1169","authenticated-orcid":false,"given":"Guilhem","family":"Fontaine","sequence":"first","affiliation":[{"name":"Universit\u00e9 Paris\u2010Saclay ENS Paris\u2010Saclay, CNRS, PPSM  Gif\u2010sur\u2010Yvette France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5612-8327","authenticated-orcid":false,"given":"R\u00e9mi","family":"M\u00e9tivier","sequence":"additional","affiliation":[{"name":"Universit\u00e9 Paris\u2010Saclay ENS Paris\u2010Saclay, CNRS, PPSM  Gif\u2010sur\u2010Yvette France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6049-6587","authenticated-orcid":false,"given":"Guillaume","family":"Laurent","sequence":"additional","affiliation":[{"name":"Universit\u00e9 Paris\u2010Saclay ENS Paris\u2010Saclay, CNRS, PPSM  Gif\u2010sur\u2010Yvette France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9003-0670","authenticated-orcid":false,"given":"R\u00e9gis","family":"Guillot","sequence":"additional","affiliation":[{"name":"Institut De Chimie Mol\u00e9culaire Et Des Mat\u00e9riaux d'Orsay CNRS UMR 8182 Universit\u00e9 Paris\u2010Saclay  Orsay Cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7664-5532","authenticated-orcid":false,"given":"Juan","family":"Xie","sequence":"additional","affiliation":[{"name":"Universit\u00e9 Paris\u2010Saclay ENS Paris\u2010Saclay, CNRS, PPSM  Gif\u2010sur\u2010Yvette France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,5]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b07531"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/cptc.202400261"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00638"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.2c01150"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205758"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr9900228"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505520"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b07839"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42004\u2010020\u201000438\u20102"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.09.047"},{"key":"e_1_2_7_12_1","first-page":"460","volume-title":"Carbohydrate 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