Cavitand-Functionalized SWCNTs for <i>N</i>-Methylammonium Detection

Dionisio, Marco; Schnorr, Jan M.; Michaelis, Vladimir K.; Griffin, Robert G.; Swager, Timothy M.; Dalcanale, Enrico

doi:10.1021/ja301174m

Cited by 62 publications

(51 citation statements)

References 40 publications

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“…[7] This high affinity for CO over O 2 of hemoglobin and myoglobin is the underlying mechanism of carbon monoxide poisoning in mammals. [8,9] Although detectors for CO are available, there remains a need for massively [16,17] Theoretical and experimental reports have suggested that CO does not engage in charge transfer with pristine SWCNTs, [18][19][20] indicating the a chemical reactive interface is necessary. Conductivity-based CO detection has been reported for carboxylate-containing, [19] deformed, [21] or doped SWCNTs, [22] as well as SWCNTs dispersed in polymers [23] or decorated with metallic nanoparticles.…”

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confidence: 99%

Bio‐Inspired Carbon Monoxide Sensors with Voltage‐Activated Sensitivity

Savagatrup

Schroeder

et al. 2017

Angewandte Chemie

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Correspondence to: Timothy M. Swager. + These authors contributed equally to this work.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.org/ 10.1002/anie.201707491. Conflict of interestThe authors declare the following competing financial interest(s): A patent has been filed on this technology. HHS Public Access Author Manuscript Author ManuscriptAuthor Manuscript Author ManuscriptCarbon monoxide (CO) outcompetes oxygen when binding to the iron center of hemeproteins, leading to a reduction in blood oxygen level and acute poisoning. Harvesting the strong specific interaction between CO and the iron porphyrin provides a highly selective and customizable sensor. We report the development of chemiresistive sensors with voltage-activated sensitivity for the detection of CO comprising iron porphyrin and functionalized single-walled carbon nanotubes (F-SWCNTs). Modulation of the gate voltage offers a predicted extra dimension for sensing. Specifically, the sensors show significant increase in sensitivity toward CO when negative gate voltage is applied. The dosimetric sensors are selective to ppm levels of CO and functional in air. UV/Vis spectroscopy, differential pulse voltammetry, and density functional theory reveal that the in situ reduction of Fe III to Fe II enhances the interaction between the F-SWCNTs and CO. Our results illustrate a new mode of sensors wherein redox active recognition units are voltageactivated to give enhanced and highly specific responses. CommunicationsRevving up for sensing: A platform for voltage-activated, chemiresistive gas detection has been delveloped based on covalently functionalized single-walled carbon nanotubes decorated with voltage-responsive chemical selectors. The sensor is highly selective towards CO in the presence of oxygen, nitrogen, and carbon dioxide and is robust to humidity and remains operational in air. KeywordsCarbon monoxide; carbon nanotubes; iron porphyrin; sensors; voltage-activated Carbon monoxide (CO) is responsible for more than half of all fatal poisoning worldwide. [1] Exposure to the colorless, tasteless, and odorless gas is difficult to discern as the initial symptoms of poisoning (headache, dizziness, and confusion) are nonspecific. In the United States, the Occupational Safety and Health Administration (OSHA) has designated permissible exposure limits of 50 ppm over eight hours and 200 ppm over five minutes. [2] The affinity of iron porphyrin towards CO is well-documented for the enzymes cytochrome P450, [3][4][5] hemoglobin, [6] and myoglobin. [7] This high affinity for CO over O 2 of hemoglobin and myoglobin is the underlying mechanism of carbon monoxide poisoning in mammals. [8,9] Although detectors for CO are available, there remains a need for massively [16,17] Theoretical and experimental reports have suggested that CO does not engage in charge transfer with pristine SWCNTs, [18][19][20] indicating the a chemical reactive interface is necessary. Conductivity...

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Bio‐Inspired Carbon Monoxide Sensors with Voltage‐Activated Sensitivity

Savagatrup

Schroeder

et al. 2017

Angewandte Chemie

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“…These coumarin-containing polymers showed moderate solubility in various common organic solvents such as THF, toluene, and CHCl 3 and can solubilize SWNTs in these solvents to different levels. All of the precursors, monomers, and polymers were characterized by 1 H NMR, 13 C NMR, and MS. Physical chemistry properties of the polymers were characterized utilizing UV-vis, TGA, and fluorescence spectroscopy.…”

Section: Discussionmentioning

confidence: 99%

“…[7][8][9] These properties have spawned investigation of SWNTs in a variety of applications, including field-effect transistors (FETs), 10,11 sensors, [12][13][14][15][16] photovoltaics, [17][18][19] flexible printed circuits, 20 touch screens, 21 microelectronic interconnects, 22 and numerous other devices. 23 However, application of these novel nanostructures is often hampered by the heterogeneous character of as-produced SWNT samples.…”

Section: Introductionmentioning

confidence: 99%

π-Conjugated polymers with pendant coumarins: design, synthesis, characterization, and interactions with carbon nanotubes

2016

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A series of new fluorene-based -conjugated polymers having coumarin derivatives as part of dendritic side chains were designed and prepared using the Suzuki-Miyaura cross-coupling reaction. A new coumarin derivative bearing a heptyl side chain for solubility was utilized to ensure solubility of the final polymers. It was found that fluorescence resonance energy transfer (FRET) from the coumrains to the polyfluorene backbone was efficient, especially for the polymers decorated with lower-generation dendrons. Each of the polymers was found to interact strongly with the surface of single-walled carbon nanotubes (SWNTs) in THF, and their ability to selectively disperse specific SWNT chiralities was investigated. Photoluminescence studies revealed that the strong polymer emission is efficiently quenched in the corresponding supramolecular complexes with SWNTs. This high quenching efficiency indicates that the coumarin-polymer FRET system can be supramolecularly bound to the surface of (SWNTs to produce an energy transfer system in which the energy absorbed by the donor coumarin chromophores is channeled to the SWNTs.Key words: conjugated polymer, carbon nanotubes, energy transfer, light harvesting.Résumé : Nous avons conçu une série de nouveaux polymères -conjugués à base de fluorène possédant des ramifications dendritiques constituées de dérivés de la coumarine. Nous avons synthétisé ces composés par couplage croisé de Suzuki-Miyaura. Nous avons utilisé un nouveau dérivé de coumarine possédant une chaîne latérale heptyle soluble en vue d'assurer la solubilité des polymères finaux. Les résultats ont révélé que le transfert d'énergie de fluorescence par résonance (FRET) des coumarines au squelette de polyfluorène était efficace, particulièrement pour les polymères substitués par des dendrons de génération inférieure. Chacun des polymères a présenté une forte interaction avec la surface de nanotubes de carbone à simple paroi (NTSP) dans le THF. En outre, nous avons étudié leur capacité à disperser sélectivement les NTSP de chiralité spécifique. Les résultats d'études de photoluminescence ont révélé que l'intense émission des polymères subit une extinction efficace dans les complexes supramoléculaires de NTSP correspondants. L'efficacité de cette extinction indique que le système de FRET de coumarines aux polymères peut être lié de façon supramoléculaire à la surface des NTSP pour constituer un système de transfert d'énergie dans lequel l'énergie absorbée par les chromophores coumariniques donneurs est canalisée dans les NTSP. [Traduit par la Rédaction] Mots-clés : polymère conjugué, nanotubes de carbone, transfert d'énergie, antenne collectrice.

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“…The peak potential values (E p ) were plotted against the logarithm of the frequencies (log f). A line was fit to the plot and from the plot n was calculated using Equation 12. The Equation giving the line was y = 0.0073x + 0.6938, with R 2 = 0.9967.…”

Section: Electrochemical Studies Of Tetraferrocenyl-cavitand (Cavitanmentioning

confidence: 99%

“…Cavitand-based sensors can operate detecting species being in the gas phase as well as in aqueous solutions [11]. Sarcosine and its ethyl ester hydrochloride in water could be detected with chemiresistor made of carbon nanotubes attached cavitand [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Electrochemical Properties of the Tetraferrocenyl‐Cavitand in Dimethyl Formamide Solvent Using Platinum and Carbon Working Electrodes

et al. 2015

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A tetraferrocenyl‐cavitand was synthesized through copper(I)‐catalyzed azide‐alkyne cycloaddition reaction. The electrochemical property of the cavitand possessing four ferrocenyl moieties at the upper rim was investigated in dimethyl formamide solvent using platinum and carbon working electrodes. Quasi reversible redox character was observed and no electrode fouling could be found. Different electrochemical methods were selected for determination of the diffusion coefficient and number of electrons taking part in the redox process of this species. Electrochemical measurements were carried out with ferrocene and the cavitand, utilizing the same cells, electrodes and conditions. The obtained results were compared.

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Cavitand-Functionalized SWCNTs for N-Methylammonium Detection

Cited by 62 publications

References 40 publications

Bio‐Inspired Carbon Monoxide Sensors with Voltage‐Activated Sensitivity

Bio‐Inspired Carbon Monoxide Sensors with Voltage‐Activated Sensitivity

π-Conjugated polymers with pendant coumarins: design, synthesis, characterization, and interactions with carbon nanotubes

Synthesis and Electrochemical Properties of the Tetraferrocenyl‐Cavitand in Dimethyl Formamide Solvent Using Platinum and Carbon Working Electrodes

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