Synthesis of Poly(arylene vinylene)s Containing Carbazole, Triphenylamine, and Phenothiazine Rings in the Backbone by Cascade Suzuki-Heck Reactions

Ivan, Teofilia; Vacareanu, Loredana; Grigoraş, Mircea

doi:10.1080/00914037.2012.664206

Cited by 12 publications

(12 citation statements)

References 28 publications

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“…The optical properties of arylenevinylene polymers are caused by the chemical and electronic structure determined by the conjugation between the carbazole unit and the spacer. This conjugation occurs through a biphenylene unit and shows a longer conjugation path and increased π-electron delocalization, when the carbazole unit is functionalized at the 2,7 position [ 19 , 20 ]. The conjugation takes place between the phenyl units and spacer in the case of 3,6 disubstituted carbazole units.…”

Section: Resultsmentioning

confidence: 99%

“…Both the yellow-colored powder polymer AMC31 [ 19 ] and green-colored powder polymer AMC30 [ 19 ] have the same structural unit (C 24 H 25 N) and are soluble in 1,2-dichlorobenzene. Details about the preparation of polymers AMC30 and AMC31 were presented in previously published papers [ 19 , 20 ]. For the synthesis of N,N′-bis-(1-dodecyl)perylene-3,4,9,10 tetracarboxylic diimide named AMC14 ( Figure 1 c), the reaction between 3,4,9,10-tetracarboxylic-perylendianhydride and dodecylamine was used as previously discussed [ 44 ].…”

Section: Methodsmentioning

confidence: 99%

“…These polymers are characterized by good absorption of the radiation from the UV region and blue-green region of the Vis spectrum (wavelength < 450 nm for AMC30 and <540 nm for AMC31) [ 19 ]. The band gap estimated from the fundamental absorption edge indicated higher value for the polymer containing carbazole-substituted units in position 3,6 (E g,AMC30 = 2.74 eV) compared to the polymer containing carbazole-substituted units in position 2,7 (E g,AMC31 = 2.10 eV) [ 19 , 20 ]. Thus, the phenyl group rings linked in para position lead to an extended conjugation along the backbone, without the participation of nitrogen atoms [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

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Effect of Aluminum Nanostructured Electrode on the Properties of Bulk Heterojunction Based Heterostructures for Electronics

et al. 2022

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The properties of organic heterostructures with mixed layers made of arylenevinylene-based polymer donor and non-fullerene perylene diimide acceptor, deposited using Matrix Assisted Pulsed Laser Evaporation on flat Al and nano-patterned Al electrodes, were investigated. The Al layer electrode deposited on the 2D array of cylindrical nanostructures with a periodicity of 1.1 µm, developed in a polymeric layer using UV-Nanoimprint Lithography, is characterized by an inflorescence-like morphology. The effect of the nanostructuring on the optical and electrical properties was studied by comparison with those of the heterostructures based on a mixed layer with fullerene derivative acceptor. The low roughness of the mixed layer deposited on flat Al was associated with high reflectance. The nano-patterning, which was preserved in the mixed layer, determining the light trapping by multiple scattering, correlated with the high roughness and led to lower reflectance. A decrease was also revealed in photoluminescence emission both at UV and Vis excitation of the mixed layer, with the non-fullerene acceptor deposited on nano-patterned Al. An injector contact behavior was highlighted for all Al/mixed layer/ITO heterostructures by I-V characteristics in dark. The current increased, independently of acceptor (fullerene or non-fullerene), in the heterostructures with nano-patterned Al electrodes for shorter conjugation length polymer donors.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effect of Aluminum Nanostructured Electrode on the Properties of Bulk Heterojunction Based Heterostructures for Electronics

et al. 2022

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“…Photophysical properties and other characteristics arise from the polymer layout and can be altered and tuned through structural modifications. Besides the central building blocks forming the conjugated backbone, contributions of substituents and functional groups can also be substantial [5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, anthracene-containing poly(arylene ethynylene)-alt-poly(phenylene vinylene)s (AnE-PVs) [14][15][16][17][18][19] in particular have been proven to be an attractive model to investigate in detail the effect of side chain engineering with regard to OPV performance. So far, a peaking efficiency of 3.8 % [20] (power conversion efficiency, PCE) in an inverted bulk-heterojunction solar cell configuration has been achieved using AnE-PVstat (in here referred as P1), a polymer obtained by polycondensating equimolar amounts of comonomers with branched (ethylhexyloxy) and linear (octyloxy) side chains (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Influence of Sidechain Elongation on Photovoltaic Response of Sidechain-Based Statistical Anthracene-Containing Copolymer

et al. 2022

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A new sidechain-based statistical anthracene-containing poly(arylene-ethynylene)-alt-poly(p-phenylene-vinylene) (P2) bearing 2-ethylhexyloxy and decyloxy side chains was synthesized to study the effect of elongating the sidechain length from octyloxy (as in P1) to decyloxy (as in P2) on the photovoltaic performance. The polymer was prepared using the Horner-Wadsworth-Emmons olefination reaction of two dialdehydes with two bisphosphonate esters. NMR and FTIR spectroscopy characterization were employed to prove the formation of the desired polymeric structure. The photophysical and electrochemical properties showed a broad spectral range of absorption in the visible region and reversible redox activity, respectively. Thermogravimetric analysis (TGA) indicated good thermal stability. Non-optimized bulk-heterojunction solar cells achieved power conversion efficiency (PCE) of 2.4 % for P2. The reduced performance of P2 compared to P1 based solar cells (PCE 3.8%) might originate from inferior nanomorphology of the active layer blend and/or the “dilution” of the photoactive conjugated backbone upon elongation of solubilising sidechains.

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High‐Performance Organic Field‐effect Transistors from Functionalized Zinc Meso‐Porphyrins

et al. 2022

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A series of new zinc porphyrins were synthesized, and their charge transport property was tuned by introducing various groups. Triarylamine was introduced to the porphyrin moiety at the meso‐position as an electron donor, enhancing the charge carrier mobility. All the synthesized zinc porphyrins are thermally stable with a decomposition temperature over 178 °C. High frontier molecular orbitals levels of these compounds make them stable donor materials. SEM analysis of zinc porphyrins fabricated by spin‐coating resulted in diversely self‐assembled films. Field‐effect transistors were fabricated using bottom‐gate/top‐contact architecture (BGTC) by solution‐processable technique. The higher charge carrier mobility of 5.17 cm2/Vs with on/off of 106 was obtained for trifluoromethyl substituted compound due to better molecular packing. In addition, GIXRD analysis revealed zinc porphyrins films crystalline nature, which supports its better charge carrier mobility. The present investigation has validated that zinc porphyrin building blocks are an attractive candidate for p‐channel OFET devices.

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Synthesis of Poly(arylene vinylene)s Containing Carbazole, Triphenylamine, and Phenothiazine Rings in the Backbone by Cascade Suzuki-Heck Reactions

Cited by 12 publications

References 28 publications

Effect of Aluminum Nanostructured Electrode on the Properties of Bulk Heterojunction Based Heterostructures for Electronics

Effect of Aluminum Nanostructured Electrode on the Properties of Bulk Heterojunction Based Heterostructures for Electronics

Influence of Sidechain Elongation on Photovoltaic Response of Sidechain-Based Statistical Anthracene-Containing Copolymer

High‐Performance Organic Field‐effect Transistors from Functionalized Zinc Meso‐Porphyrins

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