Diaroyl(methanato)boron Difluoride Compounds as Medium‐Sensitive Two‐Photon Fluorescent Probes

Cogné-Laage, Emmanuelle; Allemand, Jean-François; Ruel, O.; Baudin, Jean‐Bernard; Croquette, Vincent; Blanchard‐Desce, Mireille; Jullien, Ludovic

doi:10.1002/chem.200305321

Cited by 191 publications

(148 citation statements)

References 80 publications

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“…Beyond the anticipated red-shift, the corresponding donor-acceptor conjugated chromophores were expected to exhibit improved cross-sections for absorption at one-and twophoton. [31,32] Scheme 1 displays the different backbones that were evaluated in the present study.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

o‐Nitrobenzyl Photolabile Protecting Groups with Red‐Shifted Absorption: Syntheses and Uncaging Cross‐Sections for One‐ and Two‐Photon Excitation

Aujard

Benbrahim

Gouget

et al. 2006

Chemistry A European J

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We evaluated the o-nitrobenzyl platform for designing photolabile protecting groups with red-shifted absorption that could be photolyzed upon one- and two-photon excitation. Several synthetic pathways to build different conjugated o-nitrobenzyl backbones, as well as to vary the benzylic position, are reported. Relative to the reference 4,5-dimethoxy-2-nitrobenzyl group, several o-nitrobenzyl derivatives exhibit a large and red-shifted one-photon absorption within the near-UV range. Uncaging after one-photon excitation was studied by measuring UV-visible absorption and steady-state fluorescence emission on model caged ethers and esters. In the whole series investigated, the caged substrates were released cleanly upon photolysis. Quantum yields of uncaging after one-photon absorption lie within the 0.1-1 % range. We observed that these drop as the maximum wavelength absorption of the o-nitrobenzyl protecting group is increased. A new method based on fluorescence correlation spectroscopy (FCS) after two-photon excitation was used to measure the action uncaging cross section for two-photon excitation. The series of o-nitrobenzyl caged fluorescent coumarins investigated exhibit values within the 0.1-0.01 Goeppert-Mayer (GM) range. Such results are in line with the low quantum yields of uncaging associated with cross-sections of 1-50 GM for two-photon absorption. Although the cross-sections for one- and two-photon absorption of o-nitrobenzyl photolabile protecting groups can be readily improved, we emphasize the difficulty in enlarging the corresponding action uncaging cross-sections in view of the observed trend of their quantum yield of uncaging.

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Section: Wwwchemeurjorgmentioning

confidence: 99%

o‐Nitrobenzyl Photolabile Protecting Groups with Red‐Shifted Absorption: Syntheses and Uncaging Cross‐Sections for One‐ and Two‐Photon Excitation

Aujard

Benbrahim

Gouget

et al. 2006

Chemistry A European J

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288

292

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“…Various types of asymmetric complexes and tunable emissions have been reported. [24][25][26][27][28][29][30][31][32][33][34] Emission colors can be modulated both in the solution and in solid states. In addition, a photo-responsive ketoiminate was obtained using a dithienylethene unit.…”

Section: Building Blocks For Constructing Nanostructures and Supramolmentioning

confidence: 99%

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

2015

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The synthesis and application of organoboron complexes are a highly relevant topic owng to their unique characteristics. Based on their emissive properties, these complexes have been used to make novel optical materials and devices; boron β-diketonate is a simple and robust organoboron complex. From a series of recent studies, unique and versatile optical properties have been reported. In this review, we introduce the results of primarily recent studies on boron diketonate and related compounds containing polymers and particularly explain their optical properties. Initially, the multi-emission of boron diketonate derivatives and its application to biotechnology are explained. Next, the formation of nanostructures and its emission properties are demonstrated. The modulation of optical properties by mechanical stress is also presented. Finally, recent progress in the development of solid-emissive materials are shown with boron diketonates and their derivatives, which have aggregation-induced emission properties. The versatility of boron diketonates as a building block for the preparation of functional optical materials is the focus of this review.

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“…Such an observation is in agreement with other reports that make use of a comparable technique with unsymmetrical donor-acceptor compounds. [18,19] In the present case with 2, the maximum two-photon absorptivity at 710 nm (d max (710)) is 60 AE 10 GM at pH 2 and 15 AE 3 GM at pH 9 (1 GM = 10 À50 cm 4 s (photonmolecule) À1 ). These values compare well with the corresponding values for commonly employed pH probes (fluorescein at pH 11: d max (780) = 35 GM, F F = 0.9; pyranin backbone: d max (750) = 4 GM, F F = 0.54 [19] ).…”

mentioning

confidence: 99%

“…UV/Vis absorption and fluorescence spectra were recorded on a Kontron Uvikon-940 spectrophotometer and a Photon Technology International LPS 220 spectrofluorimeter, respectively. The two-photon excitation spectra were recorded with a homebuilt setup [18] by using the reported excitation spectrum of fluorescein for calibration. [19] All experiments were performed at 293 K in Britton-Robinson buffer solution (0.1 mol L À1 ) prepared according to the literature.…”

mentioning

confidence: 99%

An Efficient Fluorescent Probe for Ratiometric pH Measurements in Aqueous Solutions

et al. 2004

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Diaroyl(methanato)boron Difluoride Compounds as Medium‐Sensitive Two‐Photon Fluorescent Probes

Cited by 191 publications

References 80 publications

o‐Nitrobenzyl Photolabile Protecting Groups with Red‐Shifted Absorption: Syntheses and Uncaging Cross‐Sections for One‐ and Two‐Photon Excitation

o‐Nitrobenzyl Photolabile Protecting Groups with Red‐Shifted Absorption: Syntheses and Uncaging Cross‐Sections for One‐ and Two‐Photon Excitation

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

An Efficient Fluorescent Probe for Ratiometric pH Measurements in Aqueous Solutions

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