Synthesis and Properties of Aryl- and Amino-Substituted Dibenzo[b,e]phosphindolizines.

IF 3 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Akihiro Tsurusaki, Makoto Nakamura, Akihiro Komura, Ken Kamikawa
{"title":"Synthesis and Properties of Aryl- and Amino-Substituted Dibenzo[b,e]phosphindolizines.","authors":"Akihiro Tsurusaki, Makoto Nakamura, Akihiro Komura, Ken Kamikawa","doi":"10.1002/cplu.202500204","DOIUrl":null,"url":null,"abstract":"<p><p>Dibenzo[b,e]phosphindolizine oxides with five different aryl groups and a diphenylamino group at the 10-position are synthesized by the Suzuki-Miyaura cross-coupling reaction and the Buchwald-Hartwig amination reaction of 10-chlorodibenzo[b,e]phosphindolizine. The molecular structures and properties of the products are elucidated by X-ray crystallographic analysis, UV-vis spectroscopy, and electrochemical analysis. Dibenzo[b,e]phosphindolizines with p-(diphenylamino)phenyl and diphenylamino groups have smaller HOMO-LUMO gaps and higher HOMO energy levels than derivatives with methoxy and trifluoromethyl groups and without an amino group. The substituent effects are also investigated by theoretical calculations.</p>","PeriodicalId":148,"journal":{"name":"ChemPlusChem","volume":" ","pages":"e2500204"},"PeriodicalIF":3.0000,"publicationDate":"2025-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemPlusChem","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/cplu.202500204","RegionNum":4,"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

Dibenzo[b,e]phosphindolizine oxides with five different aryl groups and a diphenylamino group at the 10-position are synthesized by the Suzuki-Miyaura cross-coupling reaction and the Buchwald-Hartwig amination reaction of 10-chlorodibenzo[b,e]phosphindolizine. The molecular structures and properties of the products are elucidated by X-ray crystallographic analysis, UV-vis spectroscopy, and electrochemical analysis. Dibenzo[b,e]phosphindolizines with p-(diphenylamino)phenyl and diphenylamino groups have smaller HOMO-LUMO gaps and higher HOMO energy levels than derivatives with methoxy and trifluoromethyl groups and without an amino group. The substituent effects are also investigated by theoretical calculations.

芳基和氨基取代二苯并[b,e]膦化吡啶的合成与性能。
采用Suzuki-Miyaura交叉偶联反应和Buchwald-Hartwig胺化反应,合成了10-氯二苯并[b,e]膦化吡啶的5个不同芳基和1个10位二苯胺基的二苯并[b,e]膦化吡啶氧化物。通过x射线晶体学分析、紫外可见光谱分析和电化学分析对产物的分子结构和性质进行了表征。与含甲氧基和三氟甲基但不含氨基的衍生物相比,含对(二苯基)苯基和二苯基的二苯并[b,e]膦化肼具有更小的HOMO- lumo间隙和更高的HOMO能级。通过理论计算对取代基效应进行了研究。
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
ChemPlusChem
ChemPlusChem CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
5.90
自引率
0.00%
发文量
200
审稿时长
1 months
期刊介绍: ChemPlusChem is a peer-reviewed, general chemistry journal that brings readers the very best in multidisciplinary research centering on chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. Fully comprehensive in its scope, ChemPlusChem publishes articles covering new results from at least two different aspects (subfields) of chemistry or one of chemistry and one of another scientific discipline (one chemistry topic plus another one, hence the title ChemPlusChem). All suitable submissions undergo balanced peer review by experts in the field to ensure the highest quality, originality, relevance, significance, and validity.
×
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