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

作者: Hristina Staleva-Musto , Valentyna Kuznetsova , David Bína , Radek Litvín , Tomáš Polívka

DOI: 10.1007/S11120-019-00694-X

关键词:

摘要: We used ultrafast transient absorption spectroscopy to study excited-state dynamics of two keto-carotenoids, siphonaxanthin and siphonein. These carotenoids differ in the presence dodecanoyl-oxy group siphonein, which is attached C19 carbon on same side molecule as conjugated keto group. show that this group, though not conjugation, still capable modifying excited state properties. While spectroscopic properties siphonein are nearly identical a non-polar solvent, they become markedly different polar solvents. In having moiety, exhibits less pronounced vibrational bands spectrum has significantly enhanced characteristic features an intramolecular charge-transfer (ICT) spectra compared siphonaxanthin. The moiety also alters lifetimes S1/ICT state. For siphonaxanthin, 60, 20, 14 ps n-hexane, acetonitrile, methanol, whereas for these yield 11, 10 ps. Thus, we even non-conjugated functional can affect character By comparison with fucoxanthin acyl-oxy derivatives, position respect key feature determining whether polarity-dependent behavior or suppressed.

参考文章(40)
Li Li, Feng Hu, Yu-Qiang Chang, Yan Zhou, Peng Wang, Jian-Ping Zhang, Triplet excitation dynamics of two keto-carotenoids in n-hexane and in methanol as studied by ns flash photolysis spectroscopy Chemical Physics Letters. ,vol. 633, pp. 114- 119 ,(2015) , 10.1016/J.CPLETT.2015.05.022
Tomáš Polívka, Harry A. Frank, Miriam M. Enriquez, Dariusz M. Niedzwiedzki, Synnøve Liaaen-Jensen, Joanna Hemming, John R. Helliwell, Madeleine Helliwell, X-ray crystal structure and time-resolved spectroscopy of the blue carotenoid violerythrin. Journal of Physical Chemistry B. ,vol. 114, pp. 8760- 8769 ,(2010) , 10.1021/JP101296A
C. C. Gradinaru, J. T. M. Kennis, E. Papagiannakis, I. H. M. van Stokkum, R. J. Cogdell, G. R. Fleming, R. A. Niederman, R. van Grondelle, An unusual pathway of excitation energy deactivation in carotenoids: Singlet-to-triplet conversion on an ultrafast timescale in a photosynthetic antenna Proceedings of the National Academy of Sciences of the United States of America. ,vol. 98, pp. 2364- 2369 ,(2001) , 10.1073/PNAS.051501298
Seiji Akimoto, Tatsuya Tomo, Yukito Naitoh, Akira Otomo, Akio Murakami, Mamoru Mimuro, Identification of a new excited state responsible for the in vivo unique absorption band of siphonaxanthin in the green alga Codium fragile. Journal of Physical Chemistry B. ,vol. 111, pp. 9179- 9181 ,(2007) , 10.1021/JP071766P
Emmanouil Papagiannakis, Ivo H.M. van Stokkum, Holger Fey, Claudia Büchel, Rienk van Grondelle, Spectroscopic characterization of the excitation energy transfer in the fucoxanthin-chlorophyll protein of diatoms. Photosynthesis Research. ,vol. 86, pp. 241- 250 ,(2005) , 10.1007/S11120-005-1003-8
Harry A. Frank, James A. Bautista, Jesusa Josue, Zeus Pendon, Roger G. Hiller, Frank P. Sharples, David Gosztola, Michael R. Wasielewski, Effect of the Solvent Environment on the Spectroscopic Properties and Dynamics of the Lowest Excited States of Carotenoids The Journal of Physical Chemistry B. ,vol. 104, pp. 4569- 4577 ,(2000) , 10.1021/JP000079U
Donatas Zigmantas, Roger G. Hiller, Frank P. Sharples, Harry A. Frank, Villy Sundström, Tomáš Polívka, Effect of a conjugated carbonyl group on the photophysical properties of carotenoids Physical Chemistry Chemical Physics. ,vol. 6, pp. 3009- 3016 ,(2004) , 10.1039/B315786E
Miriam M. Enriquez, Marcel Fuciman, Amy M. LaFountain, Nicole L. Wagner, Robert R. Birge, Harry A. Frank, The intramolecular charge transfer state in carbonyl-containing polyenes and carotenoids. Journal of Physical Chemistry B. ,vol. 114, pp. 12416- 12426 ,(2010) , 10.1021/JP106113H
Donatas Zigmantas, Roger G. Hiller, Arkady Yartsev, Villy Sundström, Tomáš Polívka, Dynamics of Excited States of the Carotenoid Peridinin in Polar Solvents: Dependence on Excitation Wavelength, Viscosity, and Temperature. Journal of Physical Chemistry B. ,vol. 107, pp. 5339- 5348 ,(2003) , 10.1021/JP0272318
Seiji Akimoto, Iwao Yamazaki, Akio Murakami, Shinichi Takaichi, Mamoru Mimuro, Ultrafast excitation relaxation dynamics and energy transfer in the siphonaxanthin-containing green alga Codium fragile Chemical Physics Letters. ,vol. 390, pp. 45- 49 ,(2004) , 10.1016/J.CPLETT.2004.03.140