Synthesis and spectroscopic properties of carotenoid bis-phenylhydrazone astaxanthin: extending conjugation to a C=N group

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60076658%3A12310%2F24%3A43908440" target="_blank" >RIV/60076658:12310/24:43908440 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj02282c" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj02282c</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d4nj02282c" target="_blank" >10.1039/d4nj02282c</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and spectroscopic properties of carotenoid bis-phenylhydrazone astaxanthin: extending conjugation to a C=N group

Popis výsledku v původním jazyce

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 S-1 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.

Název v anglickém jazyce

Synthesis and spectroscopic properties of carotenoid bis-phenylhydrazone astaxanthin: extending conjugation to a C=N group

Popis výsledku anglicky

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 S-1 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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GX19-28323X" target="_blank" >GX19-28323X: Vztah mezi strukturou a funkcí karotenoidů: Nové cesty k řešení nezodpovězených otázek</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

1369-9261

Svazek periodika

48

Číslo periodika v rámci svazku

29

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

12919-12928

Kód UT WoS článku

001265385500001

EID výsledku v databázi Scopus

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