Spectral properties of several fluorene derivatives with potential as two-photon fluorescent dyes

Belfield, Kevin D.; Bondar, Mykhailo V.; Przhonska, Olga V.; Schafer, Katherine J.; Mourad, Wael

doi:10.1016/s0022-2313(02)00216-8

Cited by 48 publications

(33 citation statements)

References 9 publications

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“…Fluorescence quantum yields, Φ FL , of the investigated fluorene derivatives (see Table 1) are relatively high (Φ FL ≈0.4-1.0), and typically increase with solvent polarity (an exception is compound 3 in THF) [20,21]. The replacement of one of the diphenylamino end groups in the symmetric molecule 5 by benzothiazole (3) or styryl phenylphosphoric acid diethyl ester (11) led to an increase in the fluorescence quantum yield in all investigated solvents.…”

Section: Linear Absorption and Steady-state Fluorescencementioning

confidence: 95%

“…The absorption spectra and fluorescence lifetimes were concentration independent [20]. Additional information about the nature of the absorption bands of fluorenes can be revealed from their excitation anisotropy spectra [17,[21][22][23]. The values of fluorescence anisotropy are commonly determined as [13]:…”

Section: Linear Absorption and Steady-state Fluorescencementioning

confidence: 99%

“…19. The parameters β em were chosen in accordance with the experimentally observed range of the corresponding angles for fluorene derivatives in polyTHF [15,21,22,25]. As fol-lows from Fig.…”

Section: Fluorescence Anisotropy Of Fluorenes Under Two-photon Excitamentioning

confidence: 99%

See 2 more Smart Citations

Two-photon Absorbing Photonic Materials: From Fundamentals to Applications

Belfield

Yao

Bondar

2008

Advances in Polymer Science

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Section: Linear Absorption and Steady-state Fluorescencementioning

confidence: 95%

Section: Linear Absorption and Steady-state Fluorescencementioning

confidence: 99%

See 1 more Smart Citation

Two-photon Absorbing Photonic Materials: From Fundamentals to Applications

Belfield

Yao

Bondar

2008

Advances in Polymer Science

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“…The parameter is an indicator of the two-photon absorption efficiency, and only recently has research been reported on the design and development of very efficient 2PA dyes on the order of >10 GM units. [11][12][13][14][15][16][17][18][19][20][21][22] Much of the synthetic efforts have focused on preparing new organic dyes for a range of applications, as molecules specifically engineered for two-photon excitation may significantly outperform standard fluorophores optimized for single photon excitation. However, the identification and availability of optimized 2PA fluorophores specifically tailored for labeling biomolecules for two-photon fluorescence imaging studies are rare.…”

Section: Introductionmentioning

confidence: 99%

“…Previous studies from our laboratory have reported on the design and development of fluorene-based organic dyes with very efficient two-photon absorption and fluorescence emission properties and their use in data storage and sensing applications. [17][18][19][20][21][22][23] The fluorene ring is a -conjugated system and allows for facile synthetic manipulation, yielding dyes with tailored spectral properties. Efforts directed towards preparing reactive fluorescent dyes have been initiated with the synthesis of an amine-reactive dye (1) for labeling, e.g., lysine residues on proteins.…”

Section: Introductionmentioning

confidence: 99%

Reactive two-photon fluorescent probes for biological imaging

Belfield

Schafer²,

Yao³

et al. 2003

SPIE Proceedings

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Two-photon fluorescence microscopy is a prominent tool in biological imaging analysis. Many commercially available fluorescent dyes currently being used have sufficed for multiphoton based imaging of biological samples. While measured two-photon cross-sections (in Goppert Meyer, GM units) of some of the dyes are available, many exhibit relatively low two-photon cross-section values in the tunability range of Ti:sapphire lasers commonly used in multiphoton microscopy imaging. For example, Bodipy FL exhibits a maximum GM unit of 18 at 925 nm, compared to a range of 2-4 GM units from 775 -875 nm. Furthermore, available fluorophores may be plagued with either low fluorescence quantum yield and/or the additional problem of rapid photobleaching upon exposure to the high peak power provided by the fs laser source. In order to address the demand for better performing dyes for two-photon based imaging, we have prepared a new series of reactive fluorophores tailored for multiphoton imaging. These fluorophores are based upon the fluorene ring system, known to exhibit high fluorescence quantum yields, typically > 0.7, and possess high photostability. They have been functionalized with various moieties to act, e.g., as efficient amine-reactive fluorescent probes for the covalent attachment onto amine-containing biomolecules. Single-photon spectral characteristics, as well as measured two-photon cross sections of a reactive fluorophore and its model conjugate in solution, as well as spectral characterizations of a bovine serum albumin (BSA) conjugate are presented.

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Excited State Intramolecular Proton Transfer and Photophysics of a New Fluorenyl Two‐Photon Fluorescent Probe

et al. 2009

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The steady-state photophysical, NMR, and two-photon absorption (2PA) properties of a new fluorene derivative (1) containing the 2-(2′-hydroxyphenyl) benzothiazole (HBT) terminal construct was investigated for use as a fluorescence probe in bioimaging. A comprehensive analysis of the linear spectral properties revealed inter-and intramolecular hydrogen bonding and excited state intramolecular proton transfer (ESIPT) processes in the HBT substituent. A specific electronic model with a double minimum potential energy surface was consistent with the observed spectral properties. The 2PA spectra were obtained using a standard two-photon induced fluorescence method with femtosecond kHz laser system, affording a maximum 2PA cross section of ~600 GM, a sufficiently high value for two-photon fluorescence imaging. No dependence of two-photon absorption efficiency on solvent properties and hydrogen bonding in the HBT substituent was observed. The potential use of this fluorenyl probe in bioimaging was demonstrated via one-and two-photon fluorescence imaging of COS-7 cells.

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Spectral properties of several fluorene derivatives with potential as two-photon fluorescent dyes

Cited by 48 publications

References 9 publications

Two-photon Absorbing Photonic Materials: From Fundamentals to Applications

Two-photon Absorbing Photonic Materials: From Fundamentals to Applications

Reactive two-photon fluorescent probes for biological imaging

Excited State Intramolecular Proton Transfer and Photophysics of a New Fluorenyl Two‐Photon Fluorescent Probe

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