Absorption and emission spectroscopic characterisation of a pyrene-flavin dyad

Shirdel, Javid; Penzkofer, Alfons; Procházka, R.; Shen, Zhen; Strauß, J.; Daub, Joerg

doi:10.1016/j.chemphys.2006.11.014

Cited by 15 publications

(27 citation statements)

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“…2a and b, respectively. The absorption cross-section spectra of the approximate constituents 10-(4-bromophenyl)-3-methylisoalloxazine (BMF) [62], 10-heptyl-3-phenylphenothiazine (PPT) [62], and 1-methylpyrene (PYM) [63] in dichloromethane (for structural formulae see Fig. 1) are included in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Spectrum of PPT (10-heptyl-3-phenyl-phenothiazine) is taken from [41], and spectrum of HPT (10-heptyl-phenothiazine) is taken from [62]. Spectra of 1-methylpyrene (PYM) are taken from [63].…”

Section: Resultsmentioning

confidence: 99%

“…The fluorescence up-conversion system and method are described in [93]. A scheme of the experimental up-conversion setup is given in [63] (Fig. 2a there).…”

Section: Methodsmentioning

confidence: 99%

“…Emphasis is given to the mutual electronic interaction between the isoalloxazine, the pyrene, and the phenothiazine subunits. The photo-induced dynamics of the pyrene-flavin-phenothiazine triad PYFPT is compared with the photo-induced dynamics of the previously studied phenothiazine-isoalloxazine dyad PPF [62,69] and pyrene-isoalloxazine dyad PFD [63,69] (see structural formulae in Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…The photo-dynamics of a pyrene-flavine dyad and of a phenothiazine-flavin dyad were analysed in [63,69] and [62,69], respectively.…”

Section: Introductionmentioning

confidence: 99%

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Photo-induced dynamics in a pyrene–isoalloxazine(flavin)–phenothiazine triad

et al. 2007

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…The fluorescence up-conversion system and method are described in [93]. A scheme of the experimental up-conversion setup is given in [63] (Fig. 2a there).…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…The photo-dynamics of a pyrene-flavine dyad and of a phenothiazine-flavin dyad were analysed in [63,69] and [62,69], respectively.…”

Section: Introductionmentioning

confidence: 99%

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Photo-induced dynamics in a pyrene–isoalloxazine(flavin)–phenothiazine triad

et al. 2007

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Investigating the spectral and electrochemical properties of novel flavin‐pyrene dyads separated via variable spacer

et al. 2022

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The present manuscript describes the synthesis and the photophysical properties of a pair of novel flavin-pyrene dyads where the donor and the acceptor entities are separated via variable spacer. The dyads were well characterized using standard techniques and investigated for their photophysical and electrochemical nature. The observed absorption spectra of the dyads mainly display peaks corresponding to the individual pyrene and flavin units, with some contribution from the flavin entity in the pyrene region. While, strong emission quenching was observed for both the dyads if compared to its individual constituents. However, a careful analysis of the emission spectra and the solvent dependent studies reveals subtle difference between the two dyads. While no significant difference could be observed when excited in the flavin region; excitation at the pyrene region displays a weak and broad emission band in case of closely connected dyad. Further, the electrochemical properties were investigated by cyclic voltammetry and the reduction ability was observed to follow the trend as FlPy2 < FlPy1 < Fl.

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Further Insight into the Photostability of the Pyrene Fluorophore in Halogenated Solvents

et al. 2012

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Pyrene fluorophores of pyrene-functionalized CdSe quantum dots (QD@Py), as well as alkylpyrene and pyrene itself (Py), undergo fast degradation in aerated chloroform under ultraviolet-A (UV-A, 316<λ<400 nm) illumination. Steady-state fluorescence studies of irradiated chloroform solutions of QD@Py show formation of new bands, red-shifted compared to that of the pyrene moiety. Similar behaviour is observed for pyrene and the alkylpyrene system. Column chromatography of the pyrene photolysate in chloroform allowed us to isolate photoproducts arising from pyrene degradation, and to obtain information on the structure of the photoproducts responsible for the emission bands. The most predominant photoproducts were those originating from the reaction of pyrene with dichloromethyl radicals. The phototransformation of QD@Py and the alkylpyrene involves mainly detachment of the alkyl chain from the aromatic ring, induced also by dichloromethyl radicals, and oxidation of the alkyl chain at the benzylic position was detected as well. By contrast, these pyrene systems show a high photostability in aerated dichloromethane. Transient absorption measurements showed formation of both pyrene triplet and pyrene radical cation for all pyrene systems in these halogenated solvents. The yield of pyrene radical cations for Py is higher than for QD@Py and the alkylpyrene. In addition, pyrene radical cations were longer-lived in dichloromethane than in chloroform. The reason for the pyrene photostability in dichloromethane is the different reactivity of chloromethyl and dichloromethyl radicals towards pyrene and oxygen. These studies show that the use of dichloromethane can be a suitable alternative to chloroform when the good solubility properties of these halogenated solvents are needed to dissolve pyrene when this chromophore is used as a fluorescent probe.

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Absorption and emission spectroscopic characterisation of a pyrene-flavin dyad

Cited by 15 publications

References 50 publications

Photo-induced dynamics in a pyrene–isoalloxazine(flavin)–phenothiazine triad

Photo-induced dynamics in a pyrene–isoalloxazine(flavin)–phenothiazine triad

Investigating the spectral and electrochemical properties of novel flavin‐pyrene dyads separated via variable spacer

Further Insight into the Photostability of the Pyrene Fluorophore in Halogenated Solvents

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