Investigation of Electrochemical Copolymerization of 1‐Naphthylamineaniline in the Presence of Various Organic Sulfonic Acids

Massoumi, Bakhshali; Aghili, Hakimeh; Entezami, Ali Akbar

doi:10.1002/jccs.200900110

Cited by 6 publications

(5 citation statements)

References 16 publications

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“…However, sulfonic acids typically have lower p K a values than their sulfuric acid counterparts. Therefore, the sulfonic acid equivalent of TEBS is likely to have a p K a value similar to other sulfonic acids (−3 ≲ p K a ≲ 3) . Interestingly, during photocatalysis when ascorbic acid was present, highly acidic conditions were expected to result in a greater dissociation of TEBS than SDS due to the lower expected p K a of the sulfonic acid.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, the sulfonic acid equivalent of TEBS is likely to have a pK a value similar to other sulfonic acids (−3 ≲ pK a ≲ 3). 41 Interestingly, during photocatalysis when ascorbic acid was present, highly acidic conditions were expected to result in a greater dissociation of TEBS than SDS due to the lower expected pK a of the sulfonic acid. Hence, the use of TEBS potentially results in increased colloidal stability in acidic conditions.…”

Section: ζ Potentialmentioning

confidence: 99%

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Surfactant Effects on Hydrogen Evolution by Small-Molecule Nonfullerene Acceptor Nanoparticles

Dolan

Perrelle

Small

et al. 2022

ACS Appl. Nano Mater.

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Organic donor:acceptor semiconductor nanoparticles (NPs) formed through the miniemulsion method have been shown to be active photocatalysts. Here, we report photocatalytic hydrogen (H2) evolution under sacrificial conditions with Pt as a cocatalyst by NPs comprising only the nonfullerene acceptor Y6, stabilized by either sodium dodecyl sulfate (SDS) or the thiophene-containing surfactant 2-(3-thienyl)ethyloxybutylsulfonate sodium salt (TEBS). Typically, changes in the photocatalytic activity of donor:acceptor NPs are associated with differences in morphology due to the use of surfactants. However, as these NPs are single component, their photocatalytic activity has a significantly lower dependence on morphology than two-component donor:acceptor NPs. Results from ultrafast transient absorption spectroscopy show a minor difference between the photophysics of the TEBS- and SDS-stabilized Y6 NPs, with free charges present with either surfactant. The similar photophysics suggest that both TEBS- and SDS-stabilized Y6 NPs would be expected to have similar rates of H2 evolution. However, the results from photocatalysis show that Y6 NPs stabilized by TEBS have a H2 evolution rate 21 times higher than that of the SDS-stabilized NPs under broadband solar-like illumination (400–900 nm). Transmission electron microscopy images of the Y6 NPs show effective photodeposition of Pt on the surface of the TEBS-stabilized NPs. In contrast, photodeposition of Pt is inhibited when SDS is used. Furthermore, the ζ potential of the NPs is higher in magnitude when SDS is present. Hence, we hypothesize that SDS forms a dense, insulating layer on the NP surface which hinders the photodeposition of Pt and reduces the rate of H2 evolution. This insulating effect is absent for TEBS-stabilized Y6 NPs, allowing a high rate of H2 evolution. The TEBS-stabilized Y6 NPs have a H2 evolution rate higher than most single-component organic photocatalysts, signaling the potential use of the Y-series acceptors for H2 evolution in Z-scheme photocatalysis.

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Section: Resultsmentioning

confidence: 99%

Section: ζ Potentialmentioning

confidence: 99%

Surfactant Effects on Hydrogen Evolution by Small-Molecule Nonfullerene Acceptor Nanoparticles

Dolan

Perrelle

Small

et al. 2022

ACS Appl. Nano Mater.

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“…Our room-temperature electrical conductivity data set for p-type doping was collected from literature ,− and from our own laboratory. There were 226 different homopolymers and 65 distinct dopants in the data set, forming 398 distinct polymer–dopant combinations.…”

Section: Data Set and Machine Learning Modelsmentioning

confidence: 99%

An Informatics Approach for Designing Conducting Polymers

Sahu

Chen

et al. 2021

ACS Appl. Mater. Interfaces

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Doping conjugated polymers, which are potential candidates for the next generation of organic electronics, is an effective strategy for manipulating their electrical conductivity. However, selecting a suitable polymer–dopant combination is exceptionally challenging because of the vastness of the chemical, configurational, and morphological spaces one needs to search. In this work, high-performance surrogate models, trained on available experimentally measured data, are developed to predict the p-type electrical conductivity and are used to screen a large candidate hypothetical data set of more than 800 000 polymer–dopant combinations. Promising candidates are identified for synthesis and device fabrication. Additionally, new design guidelines are extracted that verify and extend knowledge on important molecular fragments that correlate to high conductivity. Conductivity prediction models are also deployed at for broader open-access community use.

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“…Contrary to what was expected, activation energies of the reversed (hydrolysis) reactions are inferior to the direct ones (Table 4), indicating that these reactions can't be avoided. The pKa of DBSA was predicted at -1.84 with methods based on partial charge distribution (Marvin Sketch calculator) and measured at 2.55 (Massoumi et al, 2009). Consequently, with the presence of water, it may dissociate enough to consider the presence of free hydronium ions, which would modify the mechanisms considered in molecular modeling.…”

Section: Reaction Without Catalystmentioning

confidence: 99%

Theoretical and Kinetic Analysis of the Esterification of Undecylenic Acid with Glycerol

Fabre

Boussambe

Valentin

et al. 2020

Lipids

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The synthesis of undecylenic acid partial esters can be performed at mild temperature with a classical esterification reaction catalyzed by dodecylbenzene sulfonic acid (DBSA). A semi‐empirical molecular modeling on the different reaction intermediates indicates that DBSA can strongly decrease their heats of formation through hydrogen bonding. Diester formation seems to be thermodynamically favored with a selectivity for alpha, alpha, or alpha, beta forms that depend on the geometry of the catalyst‐intermediate configuration. Triesters are not favored but a high selectivity for monoesters requires a kinetic control. Experimental approach, considering different DBSA concentrations and temperature partially confirms the theoretical predictions but surfactant properties of DBSA and monoesters may induce nonpredicted geometries. Global apparent activation energies are calculated, corresponding to the formation and hydrolysis of mono and diesters. If water trapping allows the decrease of hydrolysis reaction constants, the presence of water and subsequent phase separation may explain differences between theoretical and experimental results and could help increasing monoester selectivity.

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Investigation of Electrochemical Copolymerization of 1‐Naphthylamineaniline in the Presence of Various Organic Sulfonic Acids

Cited by 6 publications

References 16 publications

Surfactant Effects on Hydrogen Evolution by Small-Molecule Nonfullerene Acceptor Nanoparticles

Surfactant Effects on Hydrogen Evolution by Small-Molecule Nonfullerene Acceptor Nanoparticles

An Informatics Approach for Designing Conducting Polymers

Theoretical and Kinetic Analysis of the Esterification of Undecylenic Acid with Glycerol

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