Influence of single-walled carbon nanotubes enriched in semiconducting and metallic tubes on the electropolymerization of tetrabromo ortho-xylene: Insights on the synthesis mechanism of poly(ortho-phenylenevinylene)

Baibarac, M.; Nila, Andreea; Baltog, I.; Lefrant, S.; Mevellec, Jean‐Yves; Quillard, S.; Humbert, Bernard

doi:10.1016/j.eurpolymj.2017.01.015

Cited by 3 publications

(9 citation statements)

References 27 publications

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“…Not surprisingly, 1,4‐bis(dibromomethyl)benzene can furnish poly( p ‐phenylene vinylene) (PPV) chains which has found much attention in solution synthesis due to its electroluminesce [11–23] . The isomeric poly( o ‐phenylene vinylene), however, has hitherto found less attention [24–26] . When halomethyl or dihalomethyl substituents are placed in the ortho ‐positions of an arene, the analogous formation of polymers can compete with intramolecular C−C bond closure, possibly followed by dimerization.…”

Section: Introductionmentioning

confidence: 99%

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On‐Surface Debromination of 2,3‐Bis(dibromomethyl)‐ and 2,3‐Bis(bromomethyl)naphthalene: Dimerization or Polymerization?

et al. 2022

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We describe the on-surface dehalogenative homocoupling of benzylic bromides, namely bis-bromomethyl-and bis-gem-(dibromomethyl) naphthalene as a potential route to either hydrocarbon dimers or conjugated polymers on Au(111). While bis-gem-(dibromomethyl) naphthalene affords different dimers with naphthocyclobutadiene as the key intermediate, bis-bromomethyl naphthalene furnishes a poly(o-naphthylene vinylidene) as a non-conjugated polymer which undergoes dehydrogenation toward its conjugated derivative poly(o-naphthylene vinylene) upon mild annealing. A combination of scanning tunneling microscopy, non-contact atomic force microscopy and density functional theory calculations provides deep insights into the prevailing mechanisms.

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Section: Introductionmentioning

confidence: 99%

“…Despite the competition, the reactivity of halogenated ortho ‐dimethylarenes in on‐surface reactions has so far escaped attention. By contrast, the brominated ortho ‐dimethylarene derivatives have attracted much interest in solution reactions with either nucleophiles or metals [24, 26–34] …”

Section: Introductionmentioning

confidence: 99%

On‐Surface Debromination of 2,3‐Bis(dibromomethyl)‐ and 2,3‐Bis(bromomethyl)naphthalene: Dimerization or Polymerization?

et al. 2022

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“…A consequence of this progress has been a better understanding of the fundamental processes of these nanomaterials, as well as their role in applied researchers. In this context, a sustained effort was carried out in the last years in order to evidence the influence of the metallic and semiconducting tubes on both the physical properties, for example, photoluminescence (PL) [ 15 ] and applications field, for example, sensors [ 16 ], organic light-emitting diode [ 17 ], organic photovoltaic [ 18 ] and son on. Often, a CPs PL quenching process was reported to be induced by M + S-SWNTs [ 15 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

“…In this context, a sustained effort was carried out in the last years in order to evidence the influence of the metallic and semiconducting tubes on both the physical properties, for example, photoluminescence (PL) [ 15 ] and applications field, for example, sensors [ 16 ], organic light-emitting diode [ 17 ], organic photovoltaic [ 18 ] and son on. Often, a CPs PL quenching process was reported to be induced by M + S-SWNTs [ 15 , 19 ]. Depending on the energy levels diagrams of the CPs and M + S-SWNTs, the CPs PL quenching process was reported to be induced either by semiconducting tubes, either of metallic tubes [ 15 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

“…Often, a CPs PL quenching process was reported to be induced by M + S-SWNTs [ 15 , 19 ]. Depending on the energy levels diagrams of the CPs and M + S-SWNTs, the CPs PL quenching process was reported to be induced either by semiconducting tubes, either of metallic tubes [ 15 , 19 ]. In this work, the influence of M + S-SWNTs, S-SWNTs and M-SWNTs on the P3HT PL, when samples are as solution and film deposited onto rough gold supports, will be reported, too.…”

Section: Introductionmentioning

confidence: 99%

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Anisotropic Photoluminescence of Poly(3-hexyl thiophene) and Their Composites with Single-Walled Carbon Nanotubes Highly Separated in Metallic and Semiconducting Tubes

et al. 2021

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In this work, the effect of the single-walled carbon nanotubes (SWNTs) as the mixtures of metallic and semiconducting tubes (M + S-SWNTs) as well as highly separated semiconducting (S-SWNTs) and metallic (M-SWNTs) tubes on the photoluminescence (PL) of poly(3-hexyl thiophene) (P3HT) was reported. Two methods were used to prepare such composites, that is, the chemical interaction of the two constituents and the electrochemical polymerization of the 3-hexyl thiophene onto the rough Au supports modified with carbon nanotubes (CNTs). The measurements of the anisotropic PL of these composites have highlighted a significant diminution of the angle of the binding of the P3HT films electrochemical synthetized onto Au electrodes covered with M + S-SWNTs. This change was attributed to metallic tubes, as was demonstrated using the anisotropic PL measurements carried out on the P3HT/M-SWNTs and P3HT/S-SWNTs composites. Small variations in the angle of the binding were reported in the case of the composites prepared by chemical interaction of the two constituents. The proposed mechanism to explain this behavior took into account the functionalization process of CNTs with P3HT. The experimental arguments of the functionalization process of CNTs with P3HT were shown by the UV-VIS-NIR and FTIR spectroscopy as well as surface-enhanced Raman scattering (SERS). A PL quenching process of P3HT induced both in the presence of S-SWNTs and M-SWNTs was reported, too. This process origins in the various de-excitation pathways which can be developed considering the energy levels diagram of the two constituents of each studied composite.

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On‐Surface Debromination of 2,3‐Bis(dibromomethyl)‐ and 2,3‐Bis(bromomethyl)naphthalene: Dimerization or Polymerization?

et al. 2022

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We describe the on‐surface dehalogenative homocoupling of benzylic bromides, namely bis‐bromomethyl‐ and bis‐gem‐(dibromomethyl) naphthalene as a potential route to either hydrocarbon dimers or conjugated polymers on Au(111). While bis‐gem‐(dibromomethyl) naphthalene affords different dimers with naphthocyclobutadiene as the key intermediate, bis‐bromomethyl naphthalene furnishes a poly(o‐naphthylene vinylidene) as a non‐conjugated polymer which undergoes dehydrogenation toward its conjugated derivative poly(o‐naphthylene vinylene) upon mild annealing. A combination of scanning tunneling microscopy, non‐contact atomic force microscopy and density functional theory calculations provides deep insights into the prevailing mechanisms.

show abstract

Influence of single-walled carbon nanotubes enriched in semiconducting and metallic tubes on the electropolymerization of tetrabromo ortho-xylene: Insights on the synthesis mechanism of poly(ortho-phenylenevinylene)

Cited by 3 publications

References 27 publications

On‐Surface Debromination of 2,3‐Bis(dibromomethyl)‐ and 2,3‐Bis(bromomethyl)naphthalene: Dimerization or Polymerization?

On‐Surface Debromination of 2,3‐Bis(dibromomethyl)‐ and 2,3‐Bis(bromomethyl)naphthalene: Dimerization or Polymerization?

Anisotropic Photoluminescence of Poly(3-hexyl thiophene) and Their Composites with Single-Walled Carbon Nanotubes Highly Separated in Metallic and Semiconducting Tubes

On‐Surface Debromination of 2,3‐Bis(dibromomethyl)‐ and 2,3‐Bis(bromomethyl)naphthalene: Dimerization or Polymerization?

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