Xiaorong Jin, Boyu Xiao, Yutao Rao, Mingbo Zhou, Bangshao Yin, Ling Xu, Tomohiro Higashino, Atsuhiro Osuka, Jianxin Song
{"title":"Synthesis of BIII Suboxochlorins","authors":"Xiaorong Jin, Boyu Xiao, Yutao Rao, Mingbo Zhou, Bangshao Yin, Ling Xu, Tomohiro Higashino, Atsuhiro Osuka, Jianxin Song","doi":"10.1021/acs.orglett.5c00304","DOIUrl":null,"url":null,"abstract":"As a new core-modified variant of B<sup>III</sup> subporphyrins, B<sup>III</sup> suboxochlorins were synthesized from B<sup>III</sup> <i>meso</i>-2-formylphenylsubporphyrins via addition reaction with mesitylmagnesium bromide, Friedel–Crafts type cyclization effected with BF<sub>3</sub>·OEt<sub>2</sub>, and oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or AgPF<sub>6</sub>. The synthesized B<sup>III</sup> suboxochlorins are equipped with a fused and conjugated benzocyclohexene unit at the periphery and display broad and blue-shifted Soret bands and red-shifted and vibronic structured Q-bands as compared with the usual B<sup>III</sup> triarylsubporphyrins. These B<sup>III</sup> suboxochlorins emit fluorescence, showing a peak over 700 nm and a tail reaching 1000 nm with ca. 2.8% quantum yield.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"4 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00304","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
As a new core-modified variant of BIII subporphyrins, BIII suboxochlorins were synthesized from BIIImeso-2-formylphenylsubporphyrins via addition reaction with mesitylmagnesium bromide, Friedel–Crafts type cyclization effected with BF3·OEt2, and oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or AgPF6. The synthesized BIII suboxochlorins are equipped with a fused and conjugated benzocyclohexene unit at the periphery and display broad and blue-shifted Soret bands and red-shifted and vibronic structured Q-bands as compared with the usual BIII triarylsubporphyrins. These BIII suboxochlorins emit fluorescence, showing a peak over 700 nm and a tail reaching 1000 nm with ca. 2.8% quantum yield.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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