Yi Wang, Le Liu, Yutao Rao, Ling Xu, Mingbo Zhou, Bangshao Yin, Atsuhiro Osuka, Jianxin Song
{"title":"m-Pyrenisubporphyrins and Their B<sup>III</sup> Complexes and Reduced Congeners.","authors":"Yi Wang, Le Liu, Yutao Rao, Ling Xu, Mingbo Zhou, Bangshao Yin, Atsuhiro Osuka, Jianxin Song","doi":"10.1002/asia.202500693","DOIUrl":null,"url":null,"abstract":"<p><p>m-Pyrenisubporphyrins were synthesized by Pd-catalyzed cross-coupling of α,α'-diboryl-m-pyrenitripyrrane with 9,10-bis(1,1-dibromomethylenyl)anthracene followed by oxidation with DDQ. Reaction of the m-pyrenisubporphyrin with BBr<sub>3</sub> and triethylamine gave a B-hydroxy complex and an oxygen-atom-inserted product. Reaction of the m-pyrenisubporphyrin with PhBCl<sub>2</sub> and triethylamine gave a B-phenyl complex. These m-pyrenisubporphyrins show red-shifted absorption bands, reflecting the incorporated pyrene segment, but are all nonaromatic. Reduction of m-pyrenisubporphyrin with p-tosylhydrazide and K<sub>2</sub>CO<sub>3</sub> gave m-pyrenisubchlorin and m-pyrenisubbacteriochlorin, depending upon the reaction conditions. These reduced products have also been shown to be nonaromatic by the low-field shifted chemical shifts of the inner pyrrolic protons, broad and non-structured absorption bands, and small NICS values.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e00693"},"PeriodicalIF":3.3000,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202500693","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
m-Pyrenisubporphyrins were synthesized by Pd-catalyzed cross-coupling of α,α'-diboryl-m-pyrenitripyrrane with 9,10-bis(1,1-dibromomethylenyl)anthracene followed by oxidation with DDQ. Reaction of the m-pyrenisubporphyrin with BBr3 and triethylamine gave a B-hydroxy complex and an oxygen-atom-inserted product. Reaction of the m-pyrenisubporphyrin with PhBCl2 and triethylamine gave a B-phenyl complex. These m-pyrenisubporphyrins show red-shifted absorption bands, reflecting the incorporated pyrene segment, but are all nonaromatic. Reduction of m-pyrenisubporphyrin with p-tosylhydrazide and K2CO3 gave m-pyrenisubchlorin and m-pyrenisubbacteriochlorin, depending upon the reaction conditions. These reduced products have also been shown to be nonaromatic by the low-field shifted chemical shifts of the inner pyrrolic protons, broad and non-structured absorption bands, and small NICS values.
期刊介绍:
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).