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
(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
- Özcan, Emrah ; Keşan, Gürkan ; Chábera, Pavel LU ; Litvín, Radek and Polívka, Tomáš
- organization
- publishing date
- 2024
- 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}}, }