Absorption and emission spectroscopic characterization of 10-phenyl-isoalloxazine derivatives

Shirdel, Javid; Penzkofer, Alfons; Procházka, R.; Daub, Joerg; Hochmuth, Eduard; Deutzmann, Rainer

doi:10.1016/j.chemphys.2006.03.010

Cited by 8 publications

(5 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[40] Similarly the simple flavin conjugate without the pyrene attachment (Fl) displays two absorption bands in the longer wavelength region with band maxima at 330 nm and 435 nm having shoulders at around 465 and 410 nm; which arises from π-π* electronic transition of the flavin moiety. [41] While the absorption spectra for Py and Fl display bands typical to the pyrene or the flavin moiety respectively, the FlPy1 and FlPy2 display absorption bands corresponding to both pyrene and flavin constituents suggesting that the individual components retain their identity in the ground state (Figure 1). Interestingly, a subtle bathochromic shift of approximately 10 nm is observed in the pyrene region of the FlPy1 and FlPy2 absorption spectra, when compared with the pyrene spectra.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

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

et al. 2022

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Absorption cross-section spectra of investigated dyes in dichloromethane (a) and acetonitrile (b). Spectra of isoalloxazine BMF (4-bromo-10-phenyl-isoalloxazine) are taken from [61]. Spectrum of PPT (10-heptyl-3-phenyl-phenothiazine) is taken from [41], and spectrum of HPT (10-heptyl-phenothiazine) is taken from [62].…”

Section: Resultsmentioning

confidence: 99%

“…1 for structural formula) [41,[64][65][66][67][68] and on the three subchromophores (BMF, PYM, PPT) of PYFPT [40,41,[61][62][63] allow an assignment on the energetic ordering of the frontier molecular orbitals (FMOs), namely highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), as follows: E LUMO (phenothiazine) > E LUMO (pyrene) > E LUMO (flavin) and E HOMO (phenothiazine) > E HOMO (pyrene) > E HOMO (flavin). A qualitative energetic evaluation of the inter-component pathways via photo-induced electron transfer is delineated on the basis of the HOMO/LUMO schemata given in Figs.…”

Section: Discussionmentioning

confidence: 99%

“…Research on modelling the electron-transfer apparatus of cryptochromes using a three-chromophore conjugate with an isoalloxazine ( [61] and references therein) as redox-mediator and electron acceptor, phenothiazine [62, and references therein] as the molecular electron reservoir, and pyrene [63, and references therein]) as an antenna in the UV-A region (320-400 nm) was started in [40,41]. The molecular structure of the pyrene-isoalloxazine(flavin)-phenothiazine triad used in [40,41] and this work is given in Fig.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

et al. 2007

Self Cite

View full text Add to dashboard Cite

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

et al. 2012

View full text Add to dashboard Cite

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.

show abstract

Absorption and emission spectroscopic characterization of 10-phenyl-isoalloxazine derivatives

Cited by 8 publications

References 38 publications

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

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

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

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

Contact Info

Product

Resources

About