Emrah Özcan, Gürkan Keşan, Pavel Chábera, Radek Litvín and Tomáš Polívka
{"title":"类胡萝卜素双苯肼虾青素的合成和光谱特性：将共轭作用扩展至 C=N 基团","authors":"Emrah Özcan, Gürkan Keşan, Pavel Chábera, Radek Litvín and Tomáš Polívka","doi":"10.1039/D4NJ02282C","DOIUrl":null,"url":null,"abstract":"<p >We report on the synthesis and detailed spectroscopic characterization of bis-phenylhydrazone astaxanthin (<strong>BPH-Asx</strong>), a derivative of astaxanthin (<strong>Asx</strong>), in which the conjugated carbonyl group of <strong>Asx</strong> is replaced by a conjugated C<img>N bond. <strong>BPH-Asx</strong> was successfully synthesized and characterized using various spectroscopic techniques, revealing subtle changes in absorption spectra and significant alterations in excited-state dynamics compared to <strong>Asx</strong>. The results reveal a shortened S<small><sub>1</sub></small> lifetime, 1.4 ps for <strong>BPH-Asx</strong> compared to 5 ps for <strong>Asx</strong>, indicating a significant impact on its excited-state dynamics. Since no polarity-induced effect was observed for <strong>BPH-Asx</strong>, the changes induced by the conjugated C<img>N group are due to prolongation of effective conjugation. Moreover, the identification of a distinctive S* signal with a 3 ps lifetime in <strong>BPH-Asx</strong> underscores the relation between effective conjugation and presence of the S* signal that is not detected in <strong>Asx</strong>.</p>","PeriodicalId":95,"journal":{"name":"New Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7000,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and spectroscopic properties of carotenoid bis-phenylhydrazone astaxanthin: extending conjugation to a CN group†\",\"authors\":\"Emrah Özcan, Gürkan Keşan, Pavel Chábera, Radek Litvín and Tomáš Polívka\",\"doi\":\"10.1039/D4NJ02282C\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >We report on the synthesis and detailed spectroscopic characterization of bis-phenylhydrazone astaxanthin (<strong>BPH-Asx</strong>), a derivative of astaxanthin (<strong>Asx</strong>), in which the conjugated carbonyl group of <strong>Asx</strong> is replaced by a conjugated C<img>N bond. <strong>BPH-Asx</strong> was successfully synthesized and characterized using various spectroscopic techniques, revealing subtle changes in absorption spectra and significant alterations in excited-state dynamics compared to <strong>Asx</strong>. The results reveal a shortened S<small><sub>1</sub></small> lifetime, 1.4 ps for <strong>BPH-Asx</strong> compared to 5 ps for <strong>Asx</strong>, indicating a significant impact on its excited-state dynamics. Since no polarity-induced effect was observed for <strong>BPH-Asx</strong>, the changes induced by the conjugated C<img>N group are due to prolongation of effective conjugation. Moreover, the identification of a distinctive S* signal with a 3 ps lifetime in <strong>BPH-Asx</strong> underscores the relation between effective conjugation and presence of the S* signal that is not detected in <strong>Asx</strong>.</p>\",\"PeriodicalId\":95,\"journal\":{\"name\":\"New Journal of Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-07-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"New Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj02282c\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"New Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj02282c","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synthesis and spectroscopic properties of carotenoid bis-phenylhydrazone astaxanthin: extending conjugation to a CN group†
We report on the synthesis and detailed spectroscopic characterization of bis-phenylhydrazone astaxanthin (BPH-Asx), a derivative of astaxanthin (Asx), in which the conjugated carbonyl group of Asx is replaced by a conjugated CN bond. BPH-Asx was successfully synthesized and characterized using various spectroscopic techniques, revealing subtle changes in absorption spectra and significant alterations in excited-state dynamics compared to Asx. The results reveal a shortened S1 lifetime, 1.4 ps for BPH-Asx compared to 5 ps for Asx, indicating a significant impact on its excited-state dynamics. Since no polarity-induced effect was observed for BPH-Asx, the changes induced by the conjugated CN group are due to prolongation of effective conjugation. Moreover, the identification of a distinctive S* signal with a 3 ps lifetime in BPH-Asx underscores the relation between effective conjugation and presence of the S* signal that is not detected in Asx.
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