Michael Haas, Sabrina Gonglach, Stefan Müllegger, Wolfgang Schöfberger
{"title":"具有扩展π电子结构的介取代A2B分子的合成与表征。","authors":"Michael Haas, Sabrina Gonglach, Stefan Müllegger, Wolfgang Schöfberger","doi":"10.1007/s00706-017-2114-6","DOIUrl":null,"url":null,"abstract":"<p><strong>Abstract: </strong>We report the chemical synthesis and characterization of the stable 5,15-bis(pentafluorophenyl)-10-(trimethylsilylethynyl)corrole which serves as a precursor for the subsequent in situ sila-Sonogashira-cross-coupling reaction and metalation with copper(II) acetate. Under ambient conditions and a common catalyst system the reaction with 1-iodopyrene occurred within five hours. Due to the direct conjugation of the 18π-electronic system of the corrole macrocycle over the alkynyl group to the pyrene moiety the optical transitions in the Soret (B-) band Q-band region are significantly altered. The copper corrole exhibited complex hyperfine and superhyperfine structure in the EPR spectrum. The assignment of the EPR spectrum reveals the existence of an axial [CuII-cor<sup>∙+</sup>] species.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"773-781"},"PeriodicalIF":1.7000,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-2114-6","citationCount":"7","resultStr":"{\"title\":\"Synthesis and characterization of <i>meso</i>-substituted A<sub>2</sub>B corroles with extended π-electronic structure.\",\"authors\":\"Michael Haas, Sabrina Gonglach, Stefan Müllegger, Wolfgang Schöfberger\",\"doi\":\"10.1007/s00706-017-2114-6\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><strong>Abstract: </strong>We report the chemical synthesis and characterization of the stable 5,15-bis(pentafluorophenyl)-10-(trimethylsilylethynyl)corrole which serves as a precursor for the subsequent in situ sila-Sonogashira-cross-coupling reaction and metalation with copper(II) acetate. Under ambient conditions and a common catalyst system the reaction with 1-iodopyrene occurred within five hours. Due to the direct conjugation of the 18π-electronic system of the corrole macrocycle over the alkynyl group to the pyrene moiety the optical transitions in the Soret (B-) band Q-band region are significantly altered. The copper corrole exhibited complex hyperfine and superhyperfine structure in the EPR spectrum. The assignment of the EPR spectrum reveals the existence of an axial [CuII-cor<sup>∙+</sup>] species.</p><p><strong>Graphical abstract: </strong></p>\",\"PeriodicalId\":18766,\"journal\":{\"name\":\"Monatshefte Fur Chemie\",\"volume\":\"149 4\",\"pages\":\"773-781\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2018-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1007/s00706-017-2114-6\",\"citationCount\":\"7\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Monatshefte Fur Chemie\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1007/s00706-017-2114-6\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2017/11/29 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Monatshefte Fur Chemie","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s00706-017-2114-6","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2017/11/29 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synthesis and characterization of meso-substituted A2B corroles with extended π-electronic structure.
Abstract: We report the chemical synthesis and characterization of the stable 5,15-bis(pentafluorophenyl)-10-(trimethylsilylethynyl)corrole which serves as a precursor for the subsequent in situ sila-Sonogashira-cross-coupling reaction and metalation with copper(II) acetate. Under ambient conditions and a common catalyst system the reaction with 1-iodopyrene occurred within five hours. Due to the direct conjugation of the 18π-electronic system of the corrole macrocycle over the alkynyl group to the pyrene moiety the optical transitions in the Soret (B-) band Q-band region are significantly altered. The copper corrole exhibited complex hyperfine and superhyperfine structure in the EPR spectrum. The assignment of the EPR spectrum reveals the existence of an axial [CuII-cor∙+] species.
期刊介绍：
"Monatshefte für Chemie/Chemical Monthly" was originally conceived as an Austrian journal of chemistry. It has evolved into an international journal covering all branches of chemistry. Featuring the most recent advances in research in analytical chemistry, biochemistry, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, Chemical Monthly publishes refereed original papers and a section entitled "Short Communications". Reviews, symposia in print, and issues devoted to special fields will also be considered.
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