Influence of structure of poly(o-phenylenediamine) on the doping ability and conducting property

Samanta, Siddhartha; Roy, Poulomi; Kar, Pradip

doi:10.1007/s11581-016-1904-x

Cited by 19 publications

(10 citation statements)

References 38 publications

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“…In the 1 H NMR profiles of CNPs (Figure 1C), the peaks located at δ = 7.9 and 7.6 ppm of CPDs and δ = 7.9 and 7.7 ppm of CDs are attributed to H in aromatic, However, due to the influence of the −NO 2 , the peak location of No. 2 H in CPDs shifted to 8.5 ppm, while those at 6.8 and 7.1 ppm are attributed to H in primary amine groups at the edge of CPDs and CDs (Figure 1C), 15,16 In the IR spectra (Figure 1D), the absorption bands at 3363 and 3427 cm 17,18 XPS results (Figure S1) further indicate the successful synthesis of CNPs rich in phenazine and amino groups. 14 UV absorption and fluorescence spectra (Figure 2A) show that in addition to excitation-independent characteristics, CNPs also display large Stokes shifts (146 nm for CPDs, 141 nm for CDs), thereby greatly avoiding self-absorption or internal filtering effects and improving the signal-to-noise ratio (SNR) of imaging (Table S1).…”

Section: ■ Results and Discussionmentioning

confidence: 87%

“…In the 1 H NMR profiles of CNPs (Figure C), the peaks located at δ = 7.9 and 7.6 ppm of CPDs and δ = 7.9 and 7.7 ppm of CDs are attributed to H in aromatic, However, due to the influence of the −NO 2 , the peak location of No. 2 H in CPDs shifted to 8.5 ppm, while those at 6.8 and 7.1 ppm are attributed to H in primary amine groups at the edge of CPDs and CDs (Figure C), , In the IR spectra (Figure D), the absorption bands at 3363 and 3427 cm –1 in CPDs and CDs are amino groups. The absorption bands at 1507 and 1554 cm –1 in CPDs and CDs are CN in phenazine structure, while the peak at 1367 cm –1 in CPDs is associated with the stretching vibrations of CN and C–N/–NO 2 in imine and phenazine structures.…”

Section: Resultsmentioning

confidence: 94%

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One-Step Synthesis of Carbon Nanoparticles Capable of Long-Term Tracking Lipid Droplet for Real-Time Monitoring of Lipid Catabolism and Pharmacodynamic Evaluation of Lipid-Lowering Drugs

et al. 2021

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Lipid droplets (LDs) are intracellular lipid-rich organelles, which not only serve as neutral lipid reservoirs but also involve in many physiological processes and are associated with a variety of metabolic diseases and cancers. Long-term tracking of the state and behavior of LDs is of great significance but challenging. The difficulty is largely due to the lack of low cytotoxicity, high photobleaching resistance, and long intracellular retention probes that are capable of long-term tracking LDs. Herein, we report the discovery of two amphiphilic LD-targeting carbon nanoparticles (CNPs, i.e., CPDs and CDs) prepared by one-step room-temperature and hydrothermal methods. Their high lipid–water partition coefficient (log P > 2.13) and strong positive solvatochromism property ensure the quality of LD imaging. Especially, CDs exhibit favorable biocompatibility (2 mg mL–1, cell viability >90%), excellent photostability (after continuous laser irradiation on a confocal microscope for 2 h, relative FL intensity >85%), and superior intracellular retention ability, thereby enabling long-term tracking of LDs in hepatocytes for up to six passages. Based on the excellent long-term tracking ability, CDs are successfully applied to observe autophagy in a typical catabolic process and to evaluate the effect of a commonly used lipid-lowering drug atorvastatin on hepatocyte lipid uptake.

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Section: ■ Results and Discussionmentioning

confidence: 87%

Section: Resultsmentioning

confidence: 94%

One-Step Synthesis of Carbon Nanoparticles Capable of Long-Term Tracking Lipid Droplet for Real-Time Monitoring of Lipid Catabolism and Pharmacodynamic Evaluation of Lipid-Lowering Drugs

et al. 2021

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“…Then, we performed optical measurements on the purified PoPD dispersed in ethanol. The emission spectrum of PoPD in ethanol had a main peak located at 411 nm, indicating the presence of quinoid imine units (-C=N-) 54 . From the PL spectrum of the purified sample under different excitation wavelengths, the prepared PoPD had excitation-independent yellow emission (Fig.…”

Section: Resultsmentioning

confidence: 99%

Electron–phonon coupling-assisted universal red luminescence of o-phenylenediamine-based carbon dots

et al. 2022

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Due to the complex core–shell structure and variety of surface functional groups, the photoluminescence (PL) mechanism of carbon dots (CDs) remain unclear. o-Phenylenediamine (oPD), as one of the most common precursors for preparing red emissive CDs, has been extensively studied. Interestingly, most of the red emission CDs based on oPD have similar PL emission characteristics. Herein, we prepared six different oPD-based CDs and found that they had almost the same PL emission and absorption spectra after purification. Structural and spectral characterization indicated that they had similar carbon core structures but different surface polymer shells. Furthermore, single-molecule PL spectroscopy confirmed that the multi-modal emission of those CDs originated from the transitions of different vibrational energy levels of the same PL center in the carbon core. In addition, the phenomenon of “spectral splitting” of single-particle CDs was observed at low temperature, which confirmed these oPD-based CDs were unique materials with properties of both organic molecules and quantum dots. Finally, theoretical calculations revealed their potential polymerization mode and carbon core structure. Moreover, we proposed the PL mechanism of red-emitting CDs based on oPD precursors; that is, the carbon core regulates the PL emission, and the polymer shell regulates the PL intensity. Our work resolves the controversy on the PL mechanism of oPD-based red CDs. These findings provide a general guide for the mechanism exploration and structural analysis of other types of CDs.

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“…When a substituent is in the orthoposition, this monomer gives a polymer with a molecular weight of 2 × 10 3 g/mol and electrical conductivity up to 10 −3 S•cm −1 . Amino and hydroxy groups in the aromatic ring activate the oxidative polymerization, but, during the oxidation, phenylenediamines and aminophenols themselves form either low molecular weight soluble products or crosslinked polycyclic structures [28,[34][35][36][37][38][39]. The electrical conductivity of polyphenylenediamines was in the range of 10 −4 -10 −6 S•cm −1 [34,36].…”

Section: Introductionmentioning

confidence: 99%

“…Amino and hydroxy groups in the aromatic ring activate the oxidative polymerization, but, during the oxidation, phenylenediamines and aminophenols themselves form either low molecular weight soluble products or crosslinked polycyclic structures [28,[34][35][36][37][38][39]. The electrical conductivity of polyphenylenediamines was in the range of 10 −4 -10 −6 S•cm −1 [34,36]. It turned out to be impossible to polymerize the monomers with aryl substituents in the ortho-and meta-position of the benzene ring.…”

Section: Introductionmentioning

confidence: 99%

Peculiarities of Oxidative Polymerization of Diarylaminodichlorobenzoquinones

et al. 2021

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New oxidative polymerization monomers—diarylaminodichlorobenzoquinones were synthesised by alkylating aniline, m-phenylenediamine and methanilic acid with chloranil. Oxidative polymerization of diarylaminodichlorobenzoquinones was studied for the first time in relation to the concentration of the monomer, acid, and oxidant/monomer ratio. It was found that the synthesized monomers are highly active in the polymerization reaction, and the oxidation rate grows with the increase in the acid concentration. Only one arylamine group is involved in the polymerization reaction. The optimal oxidant/monomer ratio is stoichiometric for one arylamine group, despite the bifunctionality of the monomers. It was shown that the type of the substituent in the aniline ring (electron donor or electron acceptor) determines the growth of the polymer chain and the structure of the resulting conjugated polymers. A mechanism for the formation of active polymerization centers for diarylaminodichlorobenzoquinones was proposed. FTIR-, NMR-, X-ray photoelectron spectroscopy, and SEM were used to identify the structure of the synthesized monomers and polymers. The obtained polymers have an amorphous structure and a loose globular morphology. The frequency dependence of the electrical conductivity was studied.

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Influence of structure of poly(o-phenylenediamine) on the doping ability and conducting property

Cited by 19 publications

References 38 publications

One-Step Synthesis of Carbon Nanoparticles Capable of Long-Term Tracking Lipid Droplet for Real-Time Monitoring of Lipid Catabolism and Pharmacodynamic Evaluation of Lipid-Lowering Drugs

One-Step Synthesis of Carbon Nanoparticles Capable of Long-Term Tracking Lipid Droplet for Real-Time Monitoring of Lipid Catabolism and Pharmacodynamic Evaluation of Lipid-Lowering Drugs

Electron–phonon coupling-assisted universal red luminescence of o-phenylenediamine-based carbon dots

Peculiarities of Oxidative Polymerization of Diarylaminodichlorobenzoquinones

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