Two-Photon Photosensitized Production of Singlet Oxygen:  Sensitizers with Phenylene−Ethynylene-Based Chromophores

McIlroy, Sean; Cló, Emiliano; Nikolajsen, Lars; Frederiksen, Peter; Nielsen, Christian; Mikkelsen, Kurt V.; Gothelf, Kurt V.; Ogilby, Peter R.

doi:10.1021/jo0482099

Cited by 118 publications

(94 citation statements)

References 76 publications

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“…Solvents were dried by standard methods and freshly distilled prior to use. The compounds 2-bromo-1,3-diethyl-1,3,2-benzodiazaborole (1), 16 4-dimesitylborylphenylacetylene (2), 30 4-cyanophenylacetylene (4), 31 (2-trimethylsilylethynyl)thiophene (8), 32 dimesityl fluoroborane (9) 33 and 1,3-bis(2´,6´-diisopropylphenyl)imidazolium chloride 34 were prepared according to literature methods. 4-Bromobenzonitrile (6), 2-bromoaniline, pphenylenediamine, boron tribromide, sodium tetrahydridoborate, palladium acetate and tetrabutylammonium fluoride trihydrate (TBAF·3H 2 O) were purchased commercially.…”

Section: Methodsmentioning

confidence: 99%

Diazaborolyl-boryl push–pull systems with ethynylene–arylene bridges as ‘turn-on’ fluoride sensors

et al. 2012

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. (2012) 'Diazaborolyl-boryl push pull systems with ethynylene arylene bridges as`turn-on' uoride sensors. ', Dalton transactions., 41 (34). pp. 10328-10346. Further information on publisher's website:http://dx.doi.org/10.1039/c2dt30438dPublisher's copyright statement:Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. IntroductionConjugated organic molecules and polymers with three-coordinate boron units as building blocks have attracted considerable interest because of their linear and non-linear optical and electronic properties, which make them potentially useful in functional materials. 1 Three-coordinate boron generally behaves as a π-acceptor due to its vacant p-orbital, which stabilizes the LUMO of an adjacent conjugated π-electron system and thus lowers the HOMO-LUMO gap of these molecules. This field of research has been dominated by the use of the dimesitylboryl group (BMes 2 , Mes = 2,4,6-Me 3 C 6 H 2 ), in which the unsaturated boron centre is stabilized towards oxidation and hydrolysis by the steric shielding of the four orthomethyl groups. [2][3][4][5] The BMes 2 group is considered to have an acceptor strength between that of NO 2 -and CN-groups. 6,7 Such electron-deficient compounds are efficient electron-transporting and/or emitting layers in organic light emitting diodes (OLEDs). 5 Compounds with BMes 2 groups are often strongly coloured and/or luminescent, 8 which renders them useful as colorimetric or luminescent sensors for fluoride ions. [9][10][11][12][13]

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Section: Methodsmentioning

confidence: 99%

Diazaborolyl-boryl push–pull systems with ethynylene–arylene bridges as ‘turn-on’ fluoride sensors

et al. 2012

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“…Even though TPA based approaches hold a considerable advantage over conventional one-photon absorption (OPA) technique due to spatial resolution and deep penetration of long wavelength irradiation into tissues, few organic photosensitizers based on a TPA mechanism have been suggested. [53,[62][63][64][65][66][67] Among the other applications in the field of biology, the technique of two-photon laser scanning fluorescence microscopy [9,[17][18][19]68] is well-spread. For example, it enables in vivo imaging of calcium dynamics [20,69,70] or intracellular zinc.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Two‐Photon Absorption of Organic Chromophores: Theoretical and Experimental Assessments

et al. 2008

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“…Conditions which have been reported previously for the Sonogashira coupling of electron deficient 4-bromobenzonitrile with TMS-acetylene were initially employed to convert bromoarene 200 to the TMS-protected acetylene 203, Table 19 (entry 1). [256] Two equivalents of TMS-acetylene were used in this procedure, presumably due to the expected copper mediated Glaser-Hay homodimerisation side reaction, which usually occurs upon incomplete exclusion of oxygen. [257] However, despite only obtaining 17 % isolated yield of the TMS-acetylene homodimer, none of the desired product was obtained.…”

Section: Figure 116mentioning

confidence: 99%

Kinetic Template‐Guided Tethering of Fragments

2012

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This thesis is composed of two separate projects: Kinetic Template-Guided Tethering of Fragments and Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1 Degradation after DNA Damage. Kinetic Template-Guided Tethering of FragmentsThe development of a novel methodology for the site-directed discovery of small molecule, protein-binding ligands is described. The protein of interest, with a cysteine thiol (either native or engineered) adjacent to the desired binding pocket, is incubated with mixtures of low molecular weight compounds (fragments) modified with either an acrylamide or a vinyl sulfonamide capture group. Any ligand within the mixture that binds within the pocket brings the capture group into close proximity with the cysteine thiol, promoting a conjugate addition reaction at an increased rate over the background reaction. The capture reaction is designed to be slow, such that during the time course of an experiment, no adduct formation is observed unless the reaction is templated by the protein. By this method, binding ligands are rapidly identified by mass spectrometry analysis of the crude reaction mixtures. The methodology has been termed 'kinetic template-guided tethering'. Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1Degradation after DNA Damage An inhibitor described within the literature was found to attenuate the reduction of cyclin D1 after DNA damage to cells. In order to implement a two-step chemical proteomics strategy to find the molecular target of this inhibitor, a synthesis of the compound with an alkyne appendage was required. The alkyne acts as a functional handle for attachment of a reporter molecule in cells via the Huisgen cycloaddition ('Click') reaction. The design and synthesis of this inhibitor with the alkyne appendage is described.

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Two-Photon Photosensitized Production of Singlet Oxygen: Sensitizers with Phenylene−Ethynylene-Based Chromophores

Cited by 118 publications

References 76 publications

Diazaborolyl-boryl push–pull systems with ethynylene–arylene bridges as ‘turn-on’ fluoride sensors

Diazaborolyl-boryl push–pull systems with ethynylene–arylene bridges as ‘turn-on’ fluoride sensors

Enhanced Two‐Photon Absorption of Organic Chromophores: Theoretical and Experimental Assessments

Kinetic Template‐Guided Tethering of Fragments

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