Intramolecular charge-transfer state of carotenoids siphonaxanthin and siphonein: function of non-conjugated acyl-oxy group

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60076658%3A12310%2F20%3A43902334" target="_blank" >RIV/60076658:12310/20:43902334 - isvavai.cz</a>

Alternative codes found

RIV/60077344:_____/20:00532625

Result on the web

<a href="https://link.springer.com/article/10.1007%2Fs11120-019-00694-x" target="_blank" >https://link.springer.com/article/10.1007%2Fs11120-019-00694-x</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11120-019-00694-x" target="_blank" >10.1007/s11120-019-00694-x</a>

Result language

angličtina

Original language name

Intramolecular charge-transfer state of carotenoids siphonaxanthin and siphonein: function of non-conjugated acyl-oxy group

Original language description

We used ultrafast transient absorption spectroscopy to study excited-state dynamics of two keto-carotenoids, siphonaxanthin and siphonein. These two carotenoids differ in the presence of dodecanoyl-oxy group in siphonein, which is attached to the C19 carbon on the same side of the molecule as the conjugated keto group. We show that this dodecanoyl-oxy group, though not in conjugation, is still capable of modifying excited state properties. While spectroscopic properties of siphonein and siphonaxanthin are nearly identical in a non-polar solvent, they become markedly different in polar solvents. In a polar solvent, siphonein, having the dodecanoyl-oxy moiety, exhibits less pronounced vibrational bands in the absorption spectrum and has significantly enhanced characteristic features of an intramolecular charge-transfer (ICT) state in transient absorption spectra compared to siphonaxanthin. The presence of the dodecanoyl-oxy moiety also alters the lifetimes of the S-1/ICT state. For siphonaxanthin, the lifetimes are 60, 20, and 14 ps in n-hexane, acetonitrile, and methanol, whereas for siphonein these lifetimes yield 60, 11, and 10 ps. Thus, we show that even a non-conjugated functional group can affect the charge-transfer character of the S-1/ICT state. By comparison with fucoxanthin acyl-oxy derivatives, we show that position of the acyl-oxy group in respect to the conjugated keto group is the key feature determining whether the polarity-dependent behavior is enhanced or suppressed.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10610 - Biophysics

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

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

Publication year

2020

Confidentiality

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

Name of the periodical

Photosynthesis Research

ISSN

0166-8595

e-ISSN

—

Volume of the periodical

144

Issue of the periodical within the volume

2

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

9

Pages from-to

127-135

UT code for WoS article

000500626700001

EID of the result in the Scopus database

2-s2.0-85076111802