{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T01:15:27Z","timestamp":1760404527349,"version":"build-2065373602"},"reference-count":20,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2013,8,12]],"date-time":"2013-08-12T00:00:00Z","timestamp":1376265600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Luminescence"],"published-print":{"date-parts":[[2014,8]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>Three tricyclic 1,2\u2010dioxetane derivatives, 1a, 2a and 3a were synthesized from their corresponding 1,4\u2010dioxin acenaphthylene compounds, 1, 2 and 3, by reaction with singlet\u2010oxygen (<jats:sup>1<\/jats:sup>O<jats:sub>2<\/jats:sub>) in dichloromethane. Evidence for the formation of the dioxetanes 1a, 2a and 3a is provided by the chemiluminescence (CL) that corresponds to the emission from the electronically excited diesters 1b*, 2b* and 3b*, which are decomposed thermally from the dioxetanes 1a, 2a and 3a, respectively. The highly strained 1,2\u2010dioxetane ring decomposes from a twisted geometry by simultaneous cleavages of the O\u2013O and C\u2013C bonds, producing the electronically excited diester that emits CL. It was observed that the CL from compound 2a is red\u2010shifted relative to that of compounds 1a and 3a suggesting a higher degree of stabilization for the excited state by the electron\u2010donating methoxy group. Also, a study of the solvent effect on fluorescence shows a significant red\u2010shift in compound 2b, indicating a more polar excited state. The kinetics of the thermal decomposition of the 1,2\u2010dioxetanes clearly demonstrate that the CL characteristics of compound 2a are quite different from those of compounds, 1a and 3a. These results are consistent with the proposed intramolecular chemically initiated electron exchange luminescence (CIEEL) mechanism which is triggered by the electron\u2010donating group of compound 2a. Copyright \u00a9 2013 John Wiley &amp; Sons, Ltd.<jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/bio2568-gra-0001.png\" xlink:title=\"image\"\/><\/jats:p>","DOI":"10.1002\/bio.2568","type":"journal-article","created":{"date-parts":[[2013,8,12]],"date-time":"2013-08-12T03:56:05Z","timestamp":1376279765000},"page":"445-450","source":"Crossref","is-referenced-by-count":2,"title":["Substituent effects on the decomposition of chemiluminescent tricyclic aromatic dioxetanes"],"prefix":"10.1002","volume":"29","author":[{"given":"Chung\u2010Wen","family":"Sun","sequence":"first","affiliation":[{"name":"Department of Chemistry National Taiwan Normal University  Taipei 116 Taiwan, Republic of China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shun\u2010Chi","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering Ming Chi University of Technology  Taishan Taipei 243 Taiwan, Republic of China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tai\u2010Shan","family":"Fang","sequence":"additional","affiliation":[{"name":"Department of Chemistry National Taiwan Normal University  Taipei 116 Taiwan, Republic of China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2013,8,12]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/b719181b"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature04542"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp074063g"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja043295f"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0300035"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochemrev.2004.02.001"},{"key":"e_1_2_6_8_1","first-page":"366","article-title":"Chemiluminescence of organic peroxides. conversion of ground\u2010state reactants to excited\u2010state products by the chemically initiated electron\u2010exchange luminescence mechanism","volume":"12","author":"Schuster GB","year":"1979","journal-title":"J Am Chem Soc"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cp20973f"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.04.017"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/b706624d"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp973175c"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/bio.694"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)00236-1"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00457-9"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochem.2010.12.001"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00483a060"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)95720-4"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2010.04.048"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00487a077"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-12-044080-1.50010-9"}],"container-title":["Luminescence"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fbio.2568","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/bio.2568","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T20:19:11Z","timestamp":1759954751000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/bio.2568"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,8,12]]},"references-count":20,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2014,8]]}},"alternative-id":["10.1002\/bio.2568"],"URL":"https:\/\/doi.org\/10.1002\/bio.2568","archive":["Portico"],"relation":{},"ISSN":["1522-7235","1522-7243"],"issn-type":[{"type":"print","value":"1522-7235"},{"type":"electronic","value":"1522-7243"}],"subject":[],"published":{"date-parts":[[2013,8,12]]}}}