Molecular logic with ferrocene-rylene conjugates: A comparison of naphthalenediimide, naphthalimide and perylenediimide Pourbaix sensor designs

Grech, Joseph; Spiteri, Jake C.; Scerri, Glenn J.; Magri, David C.

doi:10.1016/j.ica.2022.121176

Cited by 4 publications

(6 citation statements)

References 56 publications

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“…The yields and emission enhancement are not special compared to previous reports PDI scaffold performs exceptionally well considering the fluorescence wavelen emission output is around 500 nm, excluding the presence of inner filter effect Fe 3+ concentrations, and thus yielding a robust analytical tool. The authors sho successful use of 12 in a polyurethane coating, which is able to detect premature c Compound 13 [41] resembles 11, but with a smaller polyaromatic system, s fluorophore. In contrast to previous molecular architectures, both 11 and 13 ar lated by PET mechanisms, rather than a combination of PET and ICT.…”

Section: Fc-based Ms-mlg Containing Other Fused Heterocycles As Fluor...mentioning

confidence: 99%

“…The authors justified the resul grounds of paramagnetic and/or inner filter effects, which NDI is very sensitive Other interesting work, based on the use of fused aromatic rings as the fluo of the system, was carried out by the group of Thakur, as shown in Figure 10. Compound 13 [41] resembles 11, but with a smaller polyaromatic system, similar to fluorophore. In contrast to previous molecular architectures, both 11 and 13 are modulated by PET mechanisms, rather than a combination of PET and ICT.…”

Section: Fc-based Ms-mlg Containing Other Fused Heterocycles As Fluor...mentioning

confidence: 99%

“…The authors showed the successful use of 12 in a polyurethane coating, which is able to detect premature corrosion. Compound 13 [41] resembles 11, but with a smaller polyaromatic system, similar to fluorophore. In contrast to previous molecular architectures, both 11 and 13 are modulated by PET mechanisms, rather than a combination of PET and ICT.…”

Section: Fc-based Ms-mlg Containing Other Fused Heterocycles As Fluor...mentioning

confidence: 99%

“…Finally, a summary of the previous experimental and theoretical MLG studies on compounds containing the ferrocene moiety is presented in Table 1. [23] (expt) NOT [19] (th) [20] (expt + th); [22] (expt) PASS 5 [17] (expt + th); 6 [17] (expt + th); 13 [41] (expt) [20] (expt + th); [23] (expt + th)…”

Section: Miscellaneous Mlg Systems Using Ferrocenementioning

confidence: 99%

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Molecular Logic Gates Based on Ferrocene-Containing Compounds

Tzeliou,

Zois,

Tzeli

2024

Inorganics

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Ferrocene has a unique structure, i.e., a central iron atom neatly sandwiched between two cyclopentadienyl rings, which has revolutionized the chemists’ views about how metals bind to organic π-systems. This structural arrangement leads to some fascinating chemical and photophysical properties. The last three decades, there were reports about receptor molecules that could be considered to perform simple logic operations via coupling ionic bonding or more complex molecular-recognition processes with photonic (fluorescence) signals. In these systems, chemical binding (‘input’) results in a change in fluorescence intensity (‘output’) from the receptor. It has been proven that molecules respond to changes in their environment, such as the presence of various ions, neutral species, pHs, temperatures, and viscosities. Since their first realization by de Silva, molecular logic gates have been intensively experimentally studied, with purely theoretical studies being less common. Here, we present the research that has been conducted on Molecular Logic Gates (MLGs) containing ferrocene and their applications. We categorized such systems into three families of MLGs: long-chain molecules (oligomers or polymers) that incorporate ferrocene, medium-sized molecules that incorporate ferrocene, and systems where ferrocene or its derivatives are used as external additives. Furthermore, MLGs including metal cations without the ferrocene moiety are briefly presented, while computational methodologies for an accurate theoretical study of MLG, including metal cations, are suggested. Finally, future perspectives of MLGs containing ferrocene and their applications are also presented.

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Section: Fc-based Ms-mlg Containing Other Fused Heterocycles As Fluor...mentioning

confidence: 99%

Section: Fc-based Ms-mlg Containing Other Fused Heterocycles As Fluor...mentioning

confidence: 99%

Section: Fc-based Ms-mlg Containing Other Fused Heterocycles As Fluor...mentioning

confidence: 99%

Section: Miscellaneous Mlg Systems Using Ferrocenementioning

confidence: 99%

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Molecular Logic Gates Based on Ferrocene-Containing Compounds

Tzeliou,

Zois,

Tzeli

2024

Inorganics

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“…The purpose of this study was to investigate NDIs as colorimetric and fluorimetric pH indicators as a platform for the development of Pourbaix sensors [23,24], fluorescent logic gates for acidity (pH) and oxidisability (pE), [25,26] based on photoinduced electron transfer [27]. In a recent study, we synthesized a core unsubstituted NDI molecule with an electron-donor-spacer-fluorophore-spacer-receptor format, with ferrocene as the electron donor and dimethylamino as the proton receptor [28]. We observed that the compound did not function as a H + , Fe 3+ -driven AND logic gate as observed with perylenediimide [29] and naphthalenediimide-based Pourbaix sensors [25], but rather as a two-input PASS 0 logic gate (Table 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Spectrophotometric Studies of Heterocyclic Bay-Substituted Naphthalenediimide Colorimetric pH Indicators

Magro,

Camenzuli,

Magri

2023

Chemosensors

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Four naphthalenediimide colorimetric pH indicators were synthesized with N,N-dimethylethyleneamine at the imide positions and with 5- to 7-membered heterocyclic rings at the bay positions, namely pyrrolidine, morpholine, piperidine and azepane. The pH indicators are constructed in a modular receptor–spacer–fluorophore–spacer–receptor format based on a photoinduced electron transfer (PET) design. The compounds were studied by UV–visible absorption and steady-state fluorescence spectroscopy in 1:1 (v/v) methanol/water. Brilliant colour changes are observed between pH 2 and 4 due to an internal charge transfer (ICT) mechanism. Fluorescence turn-on enhancements range from 10–37 fold; however, the maximum fluorescence quantum yield in the presence of acid is <0.004, which is below naked eye detection. Hence, from the viewpoint of a human observer, these chemosensors function as colorimetric YES logic gates, and fluorimetric PASS 0 logic gates.

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Optical and Electrochemical Chemo- and Bio-sensors

Thakur

2023

Inorganica Chimica Acta

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Molecular logic with ferrocene-rylene conjugates: A comparison of naphthalenediimide, naphthalimide and perylenediimide Pourbaix sensor designs

Cited by 4 publications

References 56 publications

Molecular Logic Gates Based on Ferrocene-Containing Compounds

Molecular Logic Gates Based on Ferrocene-Containing Compounds

Synthesis and Spectrophotometric Studies of Heterocyclic Bay-Substituted Naphthalenediimide Colorimetric pH Indicators

Optical and Electrochemical Chemo- and Bio-sensors

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