Dark and photoinduced interactions between xanthene dyes and quinones

Gutiérrez, María Isela; Garcı́a, Norman A.

doi:10.1016/s0143-7208(97)00080-6

Cited by 21 publications

(14 citation statements)

References 14 publications

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“…Quantum yields of 1 O 2 production have been investigated for a large number of sensitizers. Even for a couple of hydroxy xanthenes which show a relatively high triplet quantum yield as fluoresceine, eosin and rose bengal values for 1 O 2 production rates are reported [35,36,42]. Rhodamine dyes possess a very low triplet quantum yield (1% or less) [43].…”

Section: Introductionmentioning

confidence: 99%

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Singlet molecular oxygen photosensitized by Rhodamine dyes: correlation with photophysical properties of the sensitizers

Stracke

Heupel

Thiel

1999

Journal of Photochemistry and Photobiology A: Chemistry

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By measuring its IR phosphorescence the formation of singlet molecular oxygen 1 O 2 photosensitized by rhodamine dyes is directly proved. The 1 O 2 formation rate is compared with that expected from the low probability (≈1%) of intersystem crossing of the photosensitizers. The quantum yield for triplet population and the triplet lifetime of the investigated dyes is measured by using a laser-scanning-microscopy technique. The influence of quenching agents (nitrobenzene and COT) is discussed. It results that the formation of 1 O 2 can be prevented effectively by quenching of the S 1 or T state of the photosensitizer. The influence of the molecular ground-state oxygen 3 O 2 concentration [ 3 O 2 ] is investigated. The presence of the paramagnetic 3 O 2 leads to an increased S 1 →T intersystem crossing rate of the photosensitizers and therefore to a reinforced formation of singlet molecular oxygen. It is found for rhodamine 6G as well as for rose bengal that in air-saturated acetonitrile nearly the half of the excited dye triplets are quenched by molecular oxygen. The 1 O 2 concentration can be significantly reduced by decreasing the 3 O 2 concentration below its air saturated level.

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Section: Introductionmentioning

confidence: 99%

“…Only few experiments [40,41,[44][45][46] have been performed in order to prove the formation of 1 O 2 sensitized by rhodamine dyes. This is perhaps surprising in view of the frequently discussed relation between the photostability of xanthene dyes and the presence of 1 O 2 [35,42,[47][48][49][50][51][52][53].…”

Section: Introductionmentioning

confidence: 99%

Singlet molecular oxygen photosensitized by Rhodamine dyes: correlation with photophysical properties of the sensitizers

Stracke

Heupel

Thiel

1999

Journal of Photochemistry and Photobiology A: Chemistry

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“…These compounds have also been employed as sensitisers in photodynamic therapy (Neckers, 1989;Gutiérrez & García, 1998;Chang et al, 2008), in the food industry as additives (Tanaka, 2001;Chequer et al, 2012;Odo et al, 2012;Qi et al, 2012), in laser technologies (Ahmad et al, 2002;De et al, 2005) and as fluorescent materials for the visualisation of biomolecules (Knight & Stephens, 1989;Liu et al, 2001;Hilderbrand & Weissleder, 2007). In addition, xanthenes and their derivatives can be used as sensitisers in dye-sensitised solar cells (DSSCs) (Hara et al, 2000;Pradhan et al, 2007;Guillén et al, 2008;Sharma et al, 2009) and as hole-transporting materials in organic light-emitting devices (OLEDs) (Chu et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Efficient one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives promoted by niobium pentachloride

2014

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“…Among organic dyes, xanthene derivatives are of special interest due to their photophysical and photochemical properties, which leads towards their vast applications like, efficient laser dyes and as a fluorescent probes in various studies [4].…”

Section: Introductionmentioning

confidence: 99%

A Mechanistic Study of Photoinduced Electron Transfer from Triplet Erythrosin to Various Quinones Using Time Resolved Absorption and ESR-CIDEP Measurements

Mansha¹,

Asim²,

Grampp

et al. 2014

Zeitschrift Für Physikalische Chemie

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Photoinduced electron transfer reactions from the triplet erythrosin (Ery 2− ) dianion to various quinones (1,4-benzoquinone, 2,5-di-t-butyl-1,4-benzoquinone, duroquinone, 2,5-dichloro-1,4-benzoquinone, chloranil, bromanil, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 9,10-anthraquinone) and other organic acceptors like 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane and with tetracyano-1,4-benzoquinone (cyanil), one of the strongest oxidizing agent reported in literature ( ∘ = 0.90 V vs. SCE), were studied by laser flash photolysis in acetonitrile/water mixtures at room temperature. Quenching rate constants are obtained from Stern-Volmer plots. The measured bimolecular quenching rate constants are close to the diffusion controlled rates. Excitation of a contact radical-pair or a triplet exciplex as an intermediate in the photoinduced electron transfer reaction in a slightly polar solvent (1-propanol) is confirmed by the observation of the net absorptive chemically induced dynamic electron polarization (CIDEP) spectra. The unusual net-absorptive CIDEP spectrum is explained by spin-orbit coupling interactions due to presence of four iodine atoms in the structure of erythrosin (heavy atom effect). The dependence of the electron transfer rate constants, et , on the driving force, Δ et is slightly parabolic and indicates the Marcus Inverted Region.

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Dark and photoinduced interactions between xanthene dyes and quinones

Cited by 21 publications

References 14 publications

Singlet molecular oxygen photosensitized by Rhodamine dyes: correlation with photophysical properties of the sensitizers

Singlet molecular oxygen photosensitized by Rhodamine dyes: correlation with photophysical properties of the sensitizers

Efficient one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives promoted by niobium pentachloride

A Mechanistic Study of Photoinduced Electron Transfer from Triplet Erythrosin to Various Quinones Using Time Resolved Absorption and ESR-CIDEP Measurements

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