Characterization of novel sulfonium photoacid generators and their microwave-assisted synthesis

Yanez, Ciceron O.; Andrade, Carlos Fernando Salgueirosa de; Belfield, Kevin D.

doi:10.1039/b815831b

Cited by 67 publications

(68 citation statements)

References 27 publications

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“…Compound II exhibits a maximum 2PA cross section of ~335 GM at 730 nm. Comparing these results with our previously reported data for similar molecules that did not contain the thiophene moiety a significant increase in the 2PA cross section values was observed when the thiophenyl moiety is introduced in the fluorophore 9-14…”

Section: Resultssupporting

confidence: 87%

A Series of Fluorene-Based Two-Photon Absorbing Molecules: Synthesis, Linear and Nonlinear Characterization, and Bioimaging

et al. 2010

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The synthesis, structural, and photophysical characterization of a series of new fluorescent donoracceptor and acceptor-acceptor molecules, based on the fluorenyl ring system, with two-photon absorbing properties is described. These new compounds exhibited large Stokes shifts, high fluorescent quantum yields, and, significantly, high two-photon absorption cross sections, making them well suited for two-photon fluorescence microscopy (2PFM) imaging. Confocal and twophoton fluorescence microscopy imaging of COS-7 and HCT 116 cells incubated with probe I showed endosomal selectivity, demonstrating the potential of this class of fluorescent probes in multiphoton fluorescence microscopy.

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Section: Resultssupporting

confidence: 87%

A Series of Fluorene-Based Two-Photon Absorbing Molecules: Synthesis, Linear and Nonlinear Characterization, and Bioimaging

et al. 2010

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“…9,9-Didecyl-9 H -fluorene-2,7-dicarbaldehyde ( 9 ),29 (4-(dibutylamino)benzyl) triphenylphosphonium iodide ( 11 ),30 diethyl 4-(benzo[ d ]thiazol-2-yl)benzylphosphonate ( 12 ),31 7-bromo-9,9-didecyl-9 H -fluorene-2-carbaldehyde ( 13 ),32 4-vinyltriphenylamine ( 14 ),33 1-(bromomethyl)-4-(phenylsulfonyl)benzene ( 16 ),22 and N,N-di- n -butyl-4-vinylaniline ( 20 ),34 were prepared according to literature methods. A new route was used for the synthesis of 3 which was different from that previously reported,35 and the 1 H NMR spectrum was consistent with the previously reported spectrum.…”

Section: Methodsmentioning

confidence: 99%

Donor−Acceptor−Donor Fluorene Derivatives for Two-Photon Fluorescence Lysosomal Imaging

Yao¹,

Ahn²,

Wang³

et al. 2010

J. Org. Chem.

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As part of a strategy to achieve large two-photon absorptivity in fluorene-based probes, a series of donor-acceptor-donor (D-A-D) type derivatives were synthesized and their two-photon absorption (2PA) properties investigated. The synthesis of D-A-D fluorophores was achieved by efficient preparation of key intermediates for the introduction of central electron acceptor groups. To accomplish the synthesis of two of the new derivatives, a high yield method for a one-step direct dibromomethylation of phenyl sulfide was developed. The linear and nonlinear optical properties, including UV-vis absorption, fluorescence emission, fluorescence anisotropy, and two-photon absorption (2PA), of the new D-A-D compounds were measured and compared to their D-A or D-D counterparts. Fully conjugated acceptor moieties in the center of the D-A-D fluorophore led to the greatest increase in the 2PA cross section, while weakly conjugated central acceptors exhibited only a modest increase in the 2PA cross section relative to D-A diploar analogs. Encapsulation of the new probes in Pluronic™ F 108NF micelles, and subsequent incubation in HCT 116 cells, resulted in very high lysosomal colocalization (>0.98 colocalization coefficient) relative to commercial Lysotracker™ Red, making the micelle-encapsulated dyes particularly attractive as fluorescent probes for two-photon fluorescence microscopy lysosomal imaging.

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“…Thus, commercially available initiators do not tend to have large multiphoton absorption cross-sections at appropriate wavelengths (Yanez et al , 2009a). For this reason, some groups have focused on creating new photoinitiators or PAGs that have large δ values (Cumpston et al , 1999;Yanez et al , 2009a). These molecules typically allow MAP to be achieved at quite low intensities.…”

confidence: 98%

“…In this case, having too high an absorption cross-section can be a disadvantage because it is diffi cult to expose thick fi lms of photoresist. Thus, commercially available initiators do not tend to have large multiphoton absorption cross-sections at appropriate wavelengths (Yanez et al , 2009a). For this reason, some groups have focused on creating new photoinitiators or PAGs that have large δ values (Cumpston et al , 1999;Yanez et al , 2009a).…”

confidence: 99%

Multiphoton lithography, processing and fabrication of photonic structures

Fourkas

2012

Laser Growth and Processing of Photonic Devices

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Characterization of novel sulfonium photoacid generators and their microwave-assisted synthesis

Abstract: Microwave-assisted synthesis of triarylsulfonium salt photoacid generators (PAGs) afforded reaction times 90 to 420 times faster than conventional thermal conditions, with photoacid quantum yields of new sulfonium PAGs ranging from 0.01 to 0.4.

Cited by 67 publications

References 27 publications

A Series of Fluorene-Based Two-Photon Absorbing Molecules: Synthesis, Linear and Nonlinear Characterization, and Bioimaging

A Series of Fluorene-Based Two-Photon Absorbing Molecules: Synthesis, Linear and Nonlinear Characterization, and Bioimaging

Donor−Acceptor−Donor Fluorene Derivatives for Two-Photon Fluorescence Lysosomal Imaging

Multiphoton lithography, processing and fabrication of photonic structures

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