{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T09:19:37Z","timestamp":1785403177076,"version":"3.56.0"},"reference-count":14,"publisher":"International Union of Crystallography (IUCr)","issue":"8","license":[{"start":{"date-parts":[[2023,7,28]],"date-time":"2023-07-28T00:00:00Z","timestamp":1690502400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2023,7,28]],"date-time":"2023-07-28T00:00:00Z","timestamp":1690502400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP23K04741"],"award-info":[{"award-number":["JP23K04741"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP23K13755"],"award-info":[{"award-number":["JP23K13755"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"name":"The Okayama Foundation for Science and Technology"},{"name":"Okayama Prefecture Industrial Promotion Foundation"},{"name":"OUS Research Project","award":["OUS-RP-23-2"],"award-info":[{"award-number":["OUS-RP-23-2"]}]},{"name":"OUS Research Project","award":["OUS-RP-22-4"],"award-info":[{"award-number":["OUS-RP-22-4"]}]},{"DOI":"10.13039\/100016189","name":"Wesco Scientific Promotion Foundation","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100016189","id-type":"DOI","asserted-by":"crossref"}]},{"name":"Fukuoka Naohiko Memorial Foundation"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2023,7,14]]},"published-print":{"date-parts":[[2023,8,1]]},"abstract":"<jats:p>\n                    The dehydrobenzannulene (\n                    <jats:italic>E<\/jats:italic>\n                    ,\n                    <jats:italic>E<\/jats:italic>\n                    )-1,3-(3,4:9,10-dibenzododeca-1,11-diene-5,7-diyne-1,12-diyl)benzene, C\n                    <jats:sub>26<\/jats:sub>\n                    H\n                    <jats:sub>16<\/jats:sub>\n                    , was successfully synthesized\n                    <jats:italic>via<\/jats:italic>\n                    photocatalyst-assisted stereoselective reductive desulfonylation of 1,3-bis{1-phenylsulfonyl-2-[2-(trimethylsilylethynyl)phenyl]ethenyl}benzene, C\n                    <jats:sub>44<\/jats:sub>\n                    H\n                    <jats:sub>42<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    S\n                    <jats:sub>2<\/jats:sub>\n                    Si\n                    <jats:sub>2<\/jats:sub>\n                    , and subsequent desilylative cyclization of the resulting (\n                    <jats:italic>E<\/jats:italic>\n                    ,\n                    <jats:italic>E<\/jats:italic>\n                    )-bis-silyl-protected dienyne, C\n                    <jats:sub>32<\/jats:sub>\n                    H\n                    <jats:sub>34<\/jats:sub>\n                    Si\n                    <jats:sub>2<\/jats:sub>\n                    . The structure of the dehydrobenzannulene thus obtained was confirmed by single-crystal X-ray analysis; three benzene rings are connected to one another by a 1,3-butadiynylene and a pair of ethenylene arrays. Although the \u03c0-system expanded efficiently in the dehydrobenzannulene, it was observed that the butadiynylene and ethenylene arrays were strained, showing smaller [171.3\u2005(2)\u2013172.6\u2005(2) \u00b0] and larger bond angles [122.5\u2005(2)\u2013131.9\u2005(2)\u00b0] than the conventional bond angles, respectively. In CHCl\n                    <jats:sub>3<\/jats:sub>\n                    , the dehydrobenzannulene showed the longest absorption band at 377\u2005nm. When irradiated by UV light, it emitted fluorescence at 468\u2005nm (\u03a6\n                    <jats:sub>F<\/jats:sub>\n                    = 0.26) and 504\u2005nm (\u03a6\n                    <jats:sub>F<\/jats:sub>\n                    = 0.24) in CHCl\n                    <jats:sub>3<\/jats:sub>\n                    and in the powdered state, respectively.\n                  <\/jats:p>","DOI":"10.1107\/s2056989023006187","type":"journal-article","created":{"date-parts":[[2023,7,21]],"date-time":"2023-07-21T01:24:53Z","timestamp":1689902693000},"page":"757-761","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis, optical properties and crystal structure of (\n                    <i>E<\/i>\n                    ,\n                    <i>E<\/i>\n                    )-1,3-(3,4:9,10-dibenzododeca-1,11-diene-5,7-diyne-1,12-diyl)benzene"],"prefix":"10.1107","volume":"79","author":[{"given":"Hikaru","family":"Watanabe","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takuma","family":"Sato","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michiki","family":"Sumita","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mei","family":"Shiroyama","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daichi","family":"Sugawara","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-7698-5261","authenticated-orcid":true,"given":"Tomoki","family":"Tokuyama","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasuhiro","family":"Okuda","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kan","family":"Wakamatsu","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haruo","family":"Akashi","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02pc6pc55","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8684-2951","authenticated-orcid":true,"given":"Akihiro","family":"Orita","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05aevyc10","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2023,7,28]]},"reference":[{"key":"pk2689_bb1","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. 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