{"title":"Synthesis of Chrysene-Based Nanographenes by a Successive APEX Reaction.","authors":"Yuichi Nakashige, Hidefumi Nakatsuji, Kaho Matsushima, Kazuo Murakami, Hideto Ito, Kenichiro Itami","doi":"10.1021/prechem.5c00032","DOIUrl":null,"url":null,"abstract":"<p><p>Chrysene-based nanographenes (ChrNGs), despite their relatively small structures, have been reported to exhibit low highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gaps and strong long-wavelength fluorescence, making them attractive for various applications. However, the precise synthesis of ChrNGs remains challenging, and their availability is limited compared with other classes of nanographenes. Herein, we report the synthesis of novel ChrNGs by a successive annulative π-extension (APEX) reaction. Using diphenylacetylene and benzonaphthosilole in a Pd/<i>o</i>-chloranil catalytic system, successive APEX afforded ChrNGs of various lengths and degrees of oxidation. Furthermore, exhaustive separation and further π-extension by cyclodehydrogenation afforded ChrNGs with more flat and rigid structures. Photophysical measurements of the obtained ChrNGs showed a variety of absorption and emission properties, including intense multicolor emission.</p>","PeriodicalId":29793,"journal":{"name":"Precision Chemistry","volume":"3 9","pages":"535-540"},"PeriodicalIF":6.2000,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12458009/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Precision Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1021/prechem.5c00032","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/9/22 0:00:00","PubModel":"eCollection","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Chrysene-based nanographenes (ChrNGs), despite their relatively small structures, have been reported to exhibit low highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gaps and strong long-wavelength fluorescence, making them attractive for various applications. However, the precise synthesis of ChrNGs remains challenging, and their availability is limited compared with other classes of nanographenes. Herein, we report the synthesis of novel ChrNGs by a successive annulative π-extension (APEX) reaction. Using diphenylacetylene and benzonaphthosilole in a Pd/o-chloranil catalytic system, successive APEX afforded ChrNGs of various lengths and degrees of oxidation. Furthermore, exhaustive separation and further π-extension by cyclodehydrogenation afforded ChrNGs with more flat and rigid structures. Photophysical measurements of the obtained ChrNGs showed a variety of absorption and emission properties, including intense multicolor emission.
期刊介绍：
Chemical research focused on precision enables more controllable predictable and accurate outcomes which in turn drive innovation in measurement science sustainable materials information materials personalized medicines energy environmental science and countless other fields requiring chemical insights.Precision Chemistry provides a unique and highly focused publishing venue for fundamental applied and interdisciplinary research aiming to achieve precision calculation design synthesis manipulation measurement and manufacturing. It is committed to bringing together researchers from across the chemical sciences and the related scientific areas to showcase original research and critical reviews of exceptional quality significance and interest to the broad chemistry and scientific community.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
