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Synthesis and spectroscopic properties of carotenoid bis-phenylhydrazone astaxanthin : extending conjugation to a C 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 N group

Özcan, Emrah ; Keşan, Gürkan ; Chábera, Pavel LU ; Litvín, Radek and Polívka, Tomáš (2024) In New Journal of Chemistry 48(29). p.12919-12928
Abstract

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 C N 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 C N group are due to prolongation of... (More)

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 C N 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 C N 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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author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
New Journal of Chemistry
volume
48
issue
29
pages
10 pages
publisher
Royal Society of Chemistry
external identifiers
  • scopus:85198114504
ISSN
1144-0546
DOI
10.1039/d4nj02282c
language
English
LU publication?
yes
id
319bcd90-07f4-4b2f-8c97-274135b58b09
date added to LUP
2024-09-27 15:24:05
date last changed
2024-09-27 15:25:12
@article{319bcd90-07f4-4b2f-8c97-274135b58b09,
  abstract     = {{<p>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 C N 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<sub>1</sub> 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 C N 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.</p>}},
  author       = {{Özcan, Emrah and Keşan, Gürkan and Chábera, Pavel and Litvín, Radek and Polívka, Tomáš}},
  issn         = {{1144-0546}},
  language     = {{eng}},
  number       = {{29}},
  pages        = {{12919--12928}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{New Journal of Chemistry}},
  title        = {{Synthesis and spectroscopic properties of carotenoid bis-phenylhydrazone astaxanthin : extending conjugation to a C 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 N group}},
  url          = {{http://dx.doi.org/10.1039/d4nj02282c}},
  doi          = {{10.1039/d4nj02282c}},
  volume       = {{48}},
  year         = {{2024}},
}