Citation: Jia Ying, Shi Ying, Wang Peng, Zhang Jian-Ping. Triplet excitation dynamics of β-carotene studied in three solvents by ns flash photolysis spectroscopy[J]. Chinese Chemical Letters, ;2017, 28(1): 83-88. doi: 10.1016/j.cclet.2016.05.032 shu

Triplet excitation dynamics of β-carotene studied in three solvents by ns flash photolysis spectroscopy

Department of Chemistry, Renmin University of China, Beijing 100872, China

Corresponding author: Wang Peng, wpeng@iccas.ac.cn
Received Date: 13 April 2016
Revised Date: 9 May 2016
Accepted Date: 23 May 2016
Available Online: 11 January 2016

Figures(4)

Upon anthracene-sensitizing, triplet excitation dynamics of β-carotene (β-Car) were studied in n-hexane, in methanol, and in acetonitrile, respectively, by ns flash photolysis spectroscopy. In n-hexane, only the bleaching of the ground state absorption (GSB) and the excitation triplet (³Car^*) absorption were observed, and there were no cationic species detected. In both methanol and acetonitrile, similar excitation dynamics were observed, i.e., ³Car^* having a similar lifetime to that in n-hexane, and the immediate generation of the cation dehydrodimer (^#[Car]₂⁺) upon excitation following transformation into the radical cation Car^·+, since Car^·+ has much longer lifetime in acetonitrile than in methanol. The results prove that both solvent and carotenoid structure determine the triplet excitation mechanism. 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
- β-Carotene,
- Triplet excitation dynamics,
- Solvent effect,
- ns Flash photolysis
1. [1]
  Frank H.A., Cogdell R.J.. Carotenoids in photosynthesis[J]. Photochem. Photobiol., 1996,63:257-264. doi: 10.1111/php.1996.63.issue-3
2. [2]
  Gould S.L., Kodis G., Liddell P.A.. Artificial photosynthetic reaction centers with carotenoid antennas[J]. Tetrahedron, 2006,62:2074-2096. doi: 10.1016/j.tet.2005.06.121
3. [3]
  Holt N.E., Kennis J.T.M., Fleming G.R.. Femtosecond fluorescence upconversion studies of light harvesting by β-carotene in oxygenic photosynthetic core proteins[J]. J. Phys. Chem. B, 2004,108:19029-19035. doi: 10.1021/jp046893p
4. [4]
  Telfer A., Rivas J.D.L., Barber J.. β-Carotene within the isolated photosystem Ⅱ reaction centre:photooxidation and irreversible bleaching of this chromophore by oxidised P680[J]. Biochim. Biophys. Acta, 1991,1060:106-114. doi: 10.1016/S0005-2728(05)80125-2
5. [5]
  Faller P., Pascal A., Rutherford A.W.. b-Carotene redox reactions in photosystem Ⅱ:electron transfer pathway[J]. Biochemistry, 2001,40:6431-6440. doi: 10.1021/bi0026021
6. [6]
  Farhoosh R., Chynwat V., Gebhard R., Lugtenburg J., Frank H.A.. Triplet energy transfer between the primary donor and carotenoids in Rhodobacter sphaeroides R-26.1 reaction centers incorporated with spheroidene analogs having different extents of π-electron conjugation[J]. Photochem. Photobiol., 1997,66:97-104. doi: 10.1111/php.1997.66.issue-1
7. [7]
  Yasushi K.. New trends in photobiology:structures and functions of carotenoids in photosynthetic systems[J]. J. Photochem. Photobiol. B, 1991,9:265-280. doi: 10.1016/1011-1344(91)80165-E
8. [8]
  Holt N.E., Zigmantas D., Valkunas L.. Carotenoid cation formation and the regulation of photosynthetic light harvesting[J]. Science, 2005,307:433-436. doi: 10.1126/science.1105833
9. [9]
  Ahn T.K., Avenson T.J., Ballottari M.. Architecture of a charge-transfer state regulating light harvesting in a plant antenna protein[J]. Science, 2008,320:794-797. doi: 10.1126/science.1154800
10. [10]
  Avenson T.J., Ahn T.K., Zigmantas D.. Zeaxanthin radical cation formation in minor light-harvesting complexes of higher plant antenna[J]. J. Biol. Chem., 2008,283:3550-3558. doi: 10.1074/jbc.M705645200
11. [11]
  Avenson T.J., Ahn T.K., Niyogi K.K.. Lutein can act as a switchable charge transfer quencher in the CP26 light-harvesting complex[J]. J. Biol. Chem., 2009,284:2830-2835. doi: 10.1074/jbc.M807192200
12. [12]
  Holt N.E., Fleming G.R., Niyogi K.K.. Toward an understanding of the mechanism of nonphotochemical quenching in green plants[J]. Biochemistry, 2004,43:8281-8289. doi: 10.1021/bi0494020
13. [13]
  Frank H.A., Brudvig G.W.. Redox functions of carotenoids in photosynthesis[J]. Biochemistry, 2004,43:8607-8615. doi: 10.1021/bi0492096
14. [14]
  Hanley J., Deligiannakis Y., Pascal A., Faller P., Rutherford A.W.. Carotenoid oxidation in photosystem Ⅱ[J]. Biochemistry, 1999,38:8189-8195. doi: 10.1021/bi990633u
15. [15]
  Papagiannakis E., Kennis J.T., van Stokkum I.H.M., Cogdell R.J., van Grondelle R.. An alternative carotenoid-to-bacteriochlorophyll energy transfer pathway in photosynthetic light harvesting[J]. Proc. Natl. Acad. Sci. U.S.A., 2002,99:6017-6022. doi: 10.1073/pnas.092626599
16. [16]
  Gradinaru C.C., Kennis J.T.M., Papagiannakis E.. An unusual pathway of excitation energy deactivation in carotenoids:singlet-to-triplet conversion on an ultrafast timescale in a photosynthetic antenna[J]. Proc. Natl. Acad. Sci. U.S.A., 2001,98:2364-2369. doi: 10.1073/pnas.051501298
17. [17]
  Zhang J.P., Fujii R., Koyama Y.. The 1B_u-type singlet state of β-carotene as a precursor of the radical cation found in chloroform solution by sub-picosecond time-resolved absorption spectroscopy[J]. Chem. Phys. Lett., 2001,348:235-241. doi: 10.1016/S0009-2614(01)01157-5
18. [18]
  Han R.M., Wu Y.S., Feng J.. Radical cation generation from singlet and triplet excited states of all-trans-lycopene in chloroform[J]. Photochem. Photobiol., 2004,80:326-333. doi: 10.1562/2004-04-22-RA-147.1
19. [19]
  Gurzadyan G.G., Steenken S.. Photoionization of β-carotene via electron transfer from excited states to chlorinated hydrocarbon solvents. A picosecond transient absorption study[J]. Phys. Chem. Chem. Phys., 2002,4:2983-2988. doi: 10.1039/b201765b
20. [20]
  Fujii R., Koyama Y., Mortensen A., Skibsted L.H.. Generation of the radical cation of β-carotene in chloroform via the triplet state as revealed by time-resolved absorption spectroscopy[J]. Chem. Phys. Lett., 2000,326:33-38. doi: 10.1016/S0009-2614(00)00756-9
21. [21]
  Polívka T., Zigmantas D., Herek J.L.. The carotenoid S₁ state in LH2 complexes from purple bacteria Rhodobacter sphaeroides and Rhodopseudomonas acidophila:S₁ energies, dynamics, and carotenoid radical formation[J]. J. Phys. Chem. B, 2002,106:11016-11025. doi: 10.1021/jp025752p
22. [22]
  Polívka T., Pullerits T., Frank H.A., Cogdell R.J., Sundström V.. Ultrafast formation of a carotenoid radical in LH2 antenna complexes of purple bacteria[J]. J. Phys. Chem. B, 2004,108:15398-15407. doi: 10.1021/jp0483019
23. [23]
  Andersson P.O., Gillbro T., Ferguson L., Cogdell R.J.. Absorption spectral shifts of carotenoids related to medium polarizability[J]. Photochem. Photobiol., 1991,54:353-360. doi: 10.1111/php.1991.54.issue-3
24. [24]
  Macpherson A.N., Gillbro T.. Solvent dependence of the ultrafast S2-S1 internal conversion rate of β-carotene[J]. J. Phys. Chem. A, 1998,102:5049-5058. doi: 10.1021/jp980979z
25. [25]
  Andersson P.O., Bachilo S.M., Chen R.L., Gillbro T.. Solvent and temperature effects on dual fluorescence in a series of carotenes. Energy gap dependence of the internal conversion rate[J]. J. Phys. Chem., 1995,99:16199-16209. doi: 10.1021/j100044a002
26. [26]
  He Z.F., Gosztola D., Deng Y.. Effect of terminal groups, polyene chain length, and solvent on the first excited singlet states of carotenoids[J]. J. Phys. Chem. B, 2000,104:6668-6673. doi: 10.1021/jp0008344
27. [27]
  Frank H.A., Bautista J.A., Josue J.. Effect of the solvent environment on the spectroscopic properties and dynamics of thelowest excited states ofcarotenoids[J]. J. Phys. Chem. B, 2000,104:4569-4577. doi: 10.1021/jp000079u
28. [28]
  Akimoto S., Yokono M., Higuchi M.. Solvent effects on excitation relaxation dynamics of a keto-carotenoid, siphonaxanthin[J]. Photochem. Photobiol. Sci., 2008,7:1206-1209. doi: 10.1039/b802658k
29. [29]
  Akimoto S., Yamazaki I., Murakami A., Takaichi S., Mimuro M.. Ultrafast excitation relaxation dynamics and energy transfer in the siphonaxanthin-containing green alga Codium fragile[J]. Chem. Phys. Lett., 2004,390:45-49. doi: 10.1016/j.cplett.2004.03.140
30. [30]
  Zigmantas D., Hiller R.G., Sharples F.P.. Effect of a conjugated carbonyl group on the photophysical properties of carotenoids[J]. Phys. Chem. Chem. Phys., 2004,6:3009-3016. doi: 10.1039/B315786E
31. [31]
  Akimoto S., Tomo T., Naitoh Y.. Identification of a new excited state responsible for the in vivo unique absorption band of siphonaxanthin in the green alga Codium fragile[J]. J. Phys. Chem. B, 2007,111:9179-9181.
32. [32]
  Zigmantas D., Hiller R.G., Yartsev A., Sundström V., Polívka T.. Dynamics of excited states of the carotenoid peridinin in polar solvents:dependence on excitation wavelength, viscosity, and temperature[J]. J. Phys. Chem. B, 2003,107:5339-5348. doi: 10.1021/jp0272318
33. [33]
  Zigmantas D., Polívka T., Hiller R.G., Yartsev A., Sundström V.. Spectroscopic and dynamic properties of the peridinin lowest singlet excited states[J]. J. Phys. Chem. A, 2001,105:10296-10306. doi: 10.1021/jp010022n
34. [34]
  Premvardhan L., Sandberg D.J., Fey H.. The charge-transfer properties of the S₂ State of fucoxanthin in solution and in fucoxanthin chlorophyll-a/c₂ protein (FCP) based on Stark spectroscopy and molecular-orbital theory[J]. J. Phys. Chem. B, 2008,112:11838-11853. doi: 10.1021/jp802689p
35. [35]
  Bautista J.A., Connors R.E., Raju B.B.. Excited state properties of peridinin:observation of a solvent dependence of the lowest excited singlet state lifetime and spectral behavior unique among carotenoids[J]. J. Phys. Chem. B, 1999,103:8751-8758. doi: 10.1021/jp9916135
36. [36]
  Shima S., Ilagan R.P., Gillespie N.. Two-photon and fluorescence spectroscopy and the effect of environment on the photochemical properties of peridinin in solution and in the peridinin-chlorophyll-protein from Amphidinium carterae[J]. J. Phys. Chem. A, 2003,107:8052-8066. doi: 10.1021/jp022648z
37. [37]
  Polívka T., van Stokkum I.H.M., Zigmantas D.. Energy transfer in the major intrinsic light-harvesting complex from Amphidinium carterae[J]. Biochemistry, 2006,45:8516-8526. doi: 10.1021/bi060265b
38. [38]
  Polívka T., Sundström V.. Ultrafast dynamics of carotenoid excited states-from solution to natural and artificial systems[J]. Chem. Rev., 2004,104:2021-2072. doi: 10.1021/cr020674n
39. [39]
  Yang F., Wang T.H., Wang P.. Zhang, Mechanism of photoinduced formation fucoxanthin radical cation in organic solvents[J]. Chem. J. Chin. Univ., 2010,31:2463-2467.
40. [40]
  Kaligotla S., Doyle S., Niedzwiedzki D.M.. Triplet state spectra and dynamics of peridinin analogs having different extents of π-electron conjugation[J]. Photosynth. Res., 2010,103:167-174. doi: 10.1007/s11120-010-9535-y
41. [41]
  Fuciman M., Enriquez M.M., Kaligotla S.. Singlet and triplet state spectra and dynamics of structurally modified peridinins[J]. J. Phys. Chem. B, 2011,115:4436-4445.
42. [42]
  Fujii R., Kusumoto T., Sashima T.. Sub-μ-second time-resolved absorption spectroscopy of a polar carotenoid analogue, 2-(all-trans-retinylidene) indan-1, 3-dione; formation of the dication by direct triplet-excited sensitization[J]. J. Phys. Chem. A, 2005,109:11117-11122. doi: 10.1021/jp054436i
43. [43]
  Li L., Hu F., Chang Y.Q.. Triplet excitation dynamics of two keto-carotenoids in n-hexane and in methanol as studied by ns flash photolysis spectroscopy[J]. Chem. Phys. Lett., 2015,633:114-119. doi: 10.1016/j.cplett.2015.05.022
44. [44]
  Huo M.M., Liang R., Xing Y.D.. Side-chain effects on the solution-phase conformations and charge photogeneration dynamics of low-bandgap copolymers[J]. J. Chem. Phys., 2013,139124904. doi: 10.1063/1.4821751
45. [45]
  Billsten H.H., Pan J.X., Sinha S.. Excited-state processes in the carotenoid zeaxanthin after excess energy excitation[J]. J. Phys. Chem. A, 2005,109:6852-6859. doi: 10.1021/jp052227s
46. [46]
  Gao G.Q., Deng Y., Kispert L.D.. Photoactivated ferric chloride oxidation of carotenoids by near-UV to visible light[J]. J. Phys. Chem. B, 1997,101:7844-7849. doi: 10.1021/jp970630w
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