2009
DOI: 10.1021/ja901653u
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FerriBRIGHT: A Rationally Designed Fluorescent Probe for Redox Active Metals

Abstract: The novel catechol-BODIPY dyad, 8-(3,4-dihydroxyphenyl)-2,6-bis(ethoxycarbonyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (FerriBRIGHT) was rationally designed with the aid of computational methods. FerriBRIGHT could be prepared by standard one-pot synthesis of BODIPY fluorophores from 3,4-bis(benzyloxy)benzaldehyde (1) and 3,5-dimethyl-4-(ethoxycarbonyl)pyrrole (3); however, isolating the dipyrrin intermediate 8-[3,4-bis(benzyloxy)phenyl]-2,6-bis(ethoxycarbonyl)-1,3,5,7-tetramethyl-4,4-di… Show more

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Cited by 110 publications
(60 citation statements)
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“…The ability to tailor the photophysical properties of the parent BODIPY dye to a given application has led to the wide adoption of these fluorophores for many biological imaging and other optical studies. 4-8 …”
Section: Introductionmentioning
confidence: 99%
“…The ability to tailor the photophysical properties of the parent BODIPY dye to a given application has led to the wide adoption of these fluorophores for many biological imaging and other optical studies. 4-8 …”
Section: Introductionmentioning
confidence: 99%
“…A notable example is 16 with an uncharacteristic oxygen atom between the triphenylamine and tetrazine (Fig. 59 Oxidation of the pendant catechol to the quinone yields the emissive species. 55,56 In the neutral state, 16 is non-fluorescent due to PET from the triphenylamine to the tetrazine unit.…”
Section: Redox-luminescent Pet Switchesmentioning
confidence: 99%
“…Therefore, they are ideal gas-loading systems, capable of introducing a gaseous reagent to the MW vessel at a variety of pressures [37]. Hydrogen gas has been the most widely used gaseous reagent in MW-assisted reactions, examples including hydrogenation of olefins [38,39], hydrodechlorination [40,41], debenzylation [42,43], reductive aminations [44], azide reductions [43], and dearomitization of pyridine derivatives to form saturated piperidines [43]. Molecular oxygen [45,46], 1-propyne [47], and ethene [48,49] have also seen use as reagents in reactions using MW heating.…”
Section: Use Of Batch Mw Heating For Alkoxycarbonylation Reactionsmentioning
confidence: 99%