A Click-Generated Triazole Tethered Ferrocene−Pyrene Dyad for Dual-Mode Recognition of the Pyrophosphate Anion

Romero, T.; Caballero, Antonio; Tárraga, Alberto; Molina, Pedro

doi:10.1021/ol901308z

Cited by 139 publications

(56 citation statements)

References 48 publications

(18 reference statements)

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“…Reactions with CuSO 4 and sodium ascorbate as the traditional system for CuAAC reactions were performed in a water/ethanol mixture (PKat1) and in DMF (PKat2). [49,50] The reactions with systems of CuBr and PMDETA (PKat3) as well as CuI and DBU (PKat4), which showed their high reactivity in other CuAAC reactions previously, [10,[51][52][53] were performed in dry DMF under an argon atmosphere. For all poly-CuAAC reactions, the monomer concentrations were close to 0.2 mol Á L À1 using equimolar amounts of 3b and propargyl ether whereas the catalyst concentration was 5 mmol Á L À1 .…”

Section: Catalyst Performance In the Model System Comprising 3b And Pmentioning

confidence: 99%

An Access Route to Polyferrocenes via Modular Conjugation

Lang

Voll

Inglis

et al. 2011

Macro Chemistry & Physics

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The application of copper‐catalyzed azide/alkyne cycloaddition to monomers containing a ferrocene unit leads to polyferrocenes with ferrocene in the backbone. Catalyst performance and kinetic studies of a model system comprising 1,1'‐bis(azidoethyl)ferrocene and propargyl ether revealed the usage of CuI and DBU as the catalyst in DMF at 50 °C as efficient reaction conditions for the synthesis. The resulting polymers display molecular weight‐averages up to $\overline {M} _{{\rm n}} $ = 10 000 and $\overline {M} _{{\rm w}} $ = 33 000. The polyaddition of monomers both containing ferrocene units led to polyferrocenes with $\overline {M} _{{\rm n}} $ between 4 000 and 11 000 ($\overline {M} _{{\rm w}} $ up to 78 000). The present study thus provides a pathway to polyferrocenes based on modular ligation chemistry. magnified image

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Section: Catalyst Performance In the Model System Comprising 3b And Pmentioning

confidence: 99%

An Access Route to Polyferrocenes via Modular Conjugation

Lang

Voll

Inglis

et al. 2011

Macro Chemistry & Physics

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“…[16] In the latter part of this review, the anion recognition ability of ferrocene-functionalized dendrimers has been discussed in detail. The study carried out by Molina and co-workers can be considered as the basis for the principle of ion detection by ferrocene triazoles.…”

Section: Introductionmentioning

confidence: 99%

“…The study carried out by Molina and co-workers can be considered as the basis for the principle of ion detection by ferrocene triazoles. [16] Ferrocene-pyrene dyads 40 were synthesized from 1-azidoferrocene (2) under click conditions with alkyne-functionalized pyrene (Scheme 11). Compound 40 was used for further studies with various anions such as F À , Cl À , Br À , OAc À , NO 3 À , HSO 4 À , H 2 PO 4 À , and HP 2 O 7 3À .…”

Section: Introductionmentioning

confidence: 99%

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Ganesh

Sudhir

Kundu

et al. 2011

Chemistry An Asian Journal

121

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Click chemistry has played a significant role as a rapid and versatile strategy for conjugating two molecular fragments under very mild reaction conditions. Introduction of ferrocene-derived triazole systems using click chemistry has attracted enormous interest in various fields due to its potential applications in electrochemical techniques for detection and sensing. The present discussion focuses on the synthesis of ferrocene-triazole and the importance of using a CuAAC reaction for such conjugation. Applications of ferrocene-based click reactions in conjugate chemistry, asymmetric catalysis, medicinal chemistry, host-guest interactions, and materials chemistry have been highlighted.

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“…Binding of PPi was accompanied by significant electrochemical and fluorescence changes. [11] However, this sensor could only be used in organic solvents owing to poor solubility in aqueous media.…”

mentioning

confidence: 99%

Fluorescent and Electrochemical Sensing of Polyphosphate Nucleotides by Ferrocene Functionalised with Two Zn^II(TACN)(pyrene) Complexes

Zeng

Torriero

Bond

et al. 2010

Chemistry A European J

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The [Fc-bis{Zn(II)(TACN)(Py)}] complex, comprising two Zn(II)(TACN) ligands (Fc=ferrocene; Py=pyrene; TACN=1,4,7-triazacyclononane) bearing fluorescent pyrene chromophores linked by an electrochemically active ferrocene molecule has been synthesised in high yield through a multistep procedure. In the absence of the polyphosphate guest molecules, very weak excimer emission was observed, indicating that the two pyrene-bearing Zn(II)(TACN) units are arranged in a trans-like configuration with respect to the ferrocene bridging unit. Binding of a variety of polyphosphate anionic guests (PPi and nucleotides di- and triphosphate) promotes the interaction between pyrene units and results in an enhancement in excimer emission. Investigations of phosphate binding by (31)P NMR spectroscopy, fluorescence and electrochemical techniques confirmed a 1:1 stoichiometry for the binding of PPi and nucleotide polyphosphate anions to the bis(Zn(II)(TACN)) moiety of [Fc-bis{Zn(II)(TACN)(Py)}] and indicated that binding induces a trans to cis configuration rearrangement of the bis(Zn(II)(TACN)) complexes that is responsible for the enhancement of the pyrene excimer emission. Pyrophosphate was concluded to have the strongest affinity to [Fc-bis{Zn(II)(TACN)(Py)}] among the anions tested based on a six-fold fluorescence enhancement and 0.1 V negative shift in the potential of the ferrocene/ferrocenium couple. The binding constant for a variety of polyphosphate anions was determined from the change in the intensity of pyrene excimer emission with polyphosphate concentration, measured at 475 nm in CH(3)CN/Tris-HCl (1:9) buffer solution (10.0 mM, pH 7.4). These measurements confirmed that pyrophosphate binds more strongly (K(b)=(4.45+/-0.41) x 10(6) M(-1)) than the other nucleotide di- and triphosphates (K(b)=1-50 x 10(5) M(-1)) tested.

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A Click-Generated Triazole Tethered Ferrocene−Pyrene Dyad for Dual-Mode Recognition of the Pyrophosphate Anion

Cited by 139 publications

References 48 publications

An Access Route to Polyferrocenes via Modular Conjugation

An Access Route to Polyferrocenes via Modular Conjugation

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Fluorescent and Electrochemical Sensing of Polyphosphate Nucleotides by Ferrocene Functionalised with Two Zn^II(TACN)(pyrene) Complexes

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A Click-Generated Triazole Tethered Ferrocene−Pyrene Dyad for Dual-Mode Recognition of the Pyrophosphate Anion

Cited by 139 publications

References 48 publications

An Access Route to Polyferrocenes via Modular Conjugation

An Access Route to Polyferrocenes via Modular Conjugation

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Fluorescent and Electrochemical Sensing of Polyphosphate Nucleotides by Ferrocene Functionalised with Two ZnII(TACN)(pyrene) Complexes

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Fluorescent and Electrochemical Sensing of Polyphosphate Nucleotides by Ferrocene Functionalised with Two Zn^II(TACN)(pyrene) Complexes