Study on the photooxidation of a near-infrared-absorbing benzothiazolone cyanine dye

Chen, Ping; Li, Jun; Qian, Zhiguo; Zheng, Di; Okasaki, Tsuneki; Hayami, Masaaki

doi:10.1016/s0143-7208(97)00059-4

Cited by 49 publications

(47 citation statements)

References 10 publications

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“…On the other hand, two strong absorption peaks at 245 and 326 nm could be attributed to reaction product(s) formed by the decomposition of the dye. Although the identity of these products is not investigated in this work, it can be estimated from works dealing with the decomposition of other similar cyanine dyes (50)(51)(52). Cyanine dyes activate oxygen dissolved in aqueous solutions, yielding more reactive species, such as singlet oxygen, various radicals and peroxide.…”

Section: Figmentioning

confidence: 99%

Aggregation and Decomposition of a Pseudoisocyanine Dye in Dispersions of Layered Silicates

Bujdák

Iyi

Hrobáriková

et al. 2002

Journal of Colloid and Interface Science

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Section: Figmentioning

confidence: 99%

Aggregation and Decomposition of a Pseudoisocyanine Dye in Dispersions of Layered Silicates

Bujdák

Iyi

Hrobáriková

et al. 2002

Journal of Colloid and Interface Science

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“…From the photochemical point of view, there are two possible mechanisms for the interaction of the excited sensitizer with oxygen. 7,16,17 (i) Energy transfer, which leads to the formation of singlet oxygen: …”

Section: Resultsmentioning

confidence: 99%

Photooxidative degradation of QTX (a thioxanthone derivative)

Neumann¹,

Cavalheiro²,

Poli³

et al. 2011

J. Braz. Chem. Soc.

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solução aquosa. Os produtos resultantes foram caracterizados por HPLC/ESI-MS e a fotodegradação do corante foi acompanhada por espectroscopia de absorção. O corante apresenta duas bandas em 273 e 402 nm, que decrescem durante a irradiação, enquanto que aparece uma banda na região de 310-350 nm, típica do QTX oxidado. Novos picos devidos aos fotoprodutos da degradação de QTX foram observados por cromatografia e identificados por espectrometria de massa. Os picos em m/z 388, 420 e 270 correspondem a fotoprodutos, e o de m/z 372 é atribuído ao QTX. O pico de m/z 388 corresponde à formação de um grupo sulfóxido e o de m/z 420 sugere a formação de uma sulfona com uma hidroxila no grupo metila. O pico de m/z 270 sugere que o oxigênio reage com QTX abstraindo um hidrogênio do carbono ligado à hidroxila, simultaneamente à eliminação de um grupo amino.The photooxidative degradation of QTX (2-hydroxy-3-(3,4-dimethyl-9-oxo-9H-thioxanthen-2-yloxy)-N,N,N-trimethyl-1-propanium chloride) has been investigated and photoproducts from QTX degradation in aqueous solution were characterized using HPLC/ESI-MS. The photooxidation of the dye was monitored by electronic absorption spectroscopy. The spectrum of the dye shows bands at 273 and 402 nm. During irradiation, the intensity of these bands decreases together with the appearance of a band at 310-340 nm, typical of oxidized QTX. The chromatograms show the presence of new peaks due to photoproducts of QTX degradation that were identified by mass spectroscopy. The peaks at m/z 388, 420 and 270 were attributed to photoproducts, whereas the peak at m/z 372 is due to QTX. The peak at m/z 388 corresponds to the formation of a sulfoxide group and that at m/z 420 suggested the formation of a sulfone with a hydroxyl on the methyl group. The peak at m/z 270 suggests that oxygen reacts with QTX abstracting a hydrogen atom from the carbon bonded the hydroxyl, together with the release of the amino group.

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“…The photoinduced electron transfer process has indeed been observed for a cyanine dye in solution by using spin trapping to detect transient superoxide anion O À 2 species [43]. In one of the works both the electron transfer process and the energy transfer process from photoexcited cyanine to oxygen were observed [39]. Active oxygen species have also been generated from photoexcited fullerene C 60 [44].…”

Section: à2mentioning

confidence: 91%

“…Self-sensitized energy transfer from the triplet excited state of a cyanine dye to triplet oxygen O 2 ð 3 R À g Þ leading to reactive singlet oxygen O 2 ( 1 D g ) was found to be responsible for photofading of the dye in solution. Evidence was brought indirectly by using a spin trap [39] or by detecting the ketonic reaction products using NMR [40]. Self-sensitized photobleaching due to triplet-triplet energy transfer has also been observed in thin Cy-5 films by monitoring the singlet oxygen emission in the near infrared [41].…”

Section: à2mentioning

confidence: 99%

Enhanced cyanine solar cell performance upon oxygen doping (Organic Electronics 9 (2008) 85–94)

Fan

Hany

Moser

et al. 2009

Organic Electronics

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The effect of exposing cyanine-fullerene C 60 bilayer solar cells to ambient atmosphere is investigated. For exposure times of a few hours and concomitant light soaking, the device performance experiences a drastic power efficiency increase going from 0.14% to 1.2% measured at 30 mW/cm 2 simulated solar irradiation. The 10-fold enhancement is attributed to the photoinduced doping involving oxygen and water leading to the formation of reactive superoxide anions and mobile holes in the cyanine layer. The influence of water and dry oxygen are investigated separately. While water deteriorates the device performance, dry oxygen leads only to a partial increase of efficiency. Annealing does not ameliorate the performance of doped devices. Although then the cyanine layer features more crystallinity, the considerable morphological changes cause diffusional loss in charge carrier collection. Doping of not annealed devices brings a sizeable efficiency enhancement that highlights the importance of charge carrier transport in cyanine dye based solar cells.

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Study on the photooxidation of a near-infrared-absorbing benzothiazolone cyanine dye

Cited by 49 publications

References 10 publications

Aggregation and Decomposition of a Pseudoisocyanine Dye in Dispersions of Layered Silicates

Aggregation and Decomposition of a Pseudoisocyanine Dye in Dispersions of Layered Silicates

Photooxidative degradation of QTX (a thioxanthone derivative)

Enhanced cyanine solar cell performance upon oxygen doping (Organic Electronics 9 (2008) 85–94)

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