m-Pyrenisubporphyrins and Their BIII Complexes and Reduced Congeners.

IF 3.3 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
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.

间芘异亚卟啉及其BIII配合物和还原同系物。
采用pd催化α,α′-二硼基-m-芘硝基吡喃与9,10-二(1,1-二溴亚甲基)蒽交叉偶联,DDQ氧化合成间芘异亚卟啉。间芘异亚卟啉与BBr3和三乙胺反应得到b -羟基配合物和一个插入氧原子的产物。间芘异亚卟啉与PhBCl2和三乙胺反应得到b -苯基配合物。这些间芘异亚卟啉表现出红移的吸收带,反映了合并的芘部分,但都是非芳香的。对甲酰基肼和K2CO3还原间芘异亚卟啉,根据反应条件不同,得到间芘异亚氯和间芘异亚细菌氯。这些还原产物也被证明是非芳香族的,通过低场位移的内部吡啶质子的化学位移,宽和非结构化的吸收带,和小NICS值。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Chemistry - An Asian Journal
Chemistry - An Asian Journal 化学-化学综合
CiteScore
7.00
自引率
2.40%
发文量
535
审稿时长
1.3 months
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).
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信