Synthesis of 2,7-Carbazolenevinylene-Based Copolymers and Characterization of Their Photovoltaic Properties

Leclerc, Nicolas; Michaud, Alain; Sirois, Katia; Morin, Jean‐François; Leclerc, Mario

doi:10.1002/adfm.200600171

Cited by 119 publications

(88 citation statements)

References 40 publications

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“…[15,16] In parallel, oligo-and poly(2,7-carbazole) derivatives have been successfully used in polymer lightemitting diodes (PLEDs) [17] and organic field-effect transistors (OFETs), [17,18] demonstrating good p-type transport properties. Recently, Müllen and co-workers [19] have reported solar cells with an efficiency of 0.6 % with poly(N-alkyl-2,7-carbazole), whereas Leclerc and co-workers [20] have shown an efficiency of 0.8 % with poly(2,7-carbazolenevinylene) derivatives. Moreover, in contrast with the fluorene unit the carbazole moiety is fully aromatic, providing a better chemical and environmental stability.…”

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confidence: 97%

A Low‐Bandgap Poly(2,7‐Carbazole) Derivative for Use in High‐Performance Solar Cells

2007

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Harvesting energy directly from sunlight using photovoltaic cells (PCs) is a very important way to address growing global energy needs with a renewable resource while minimizing detrimental effects on the environment. For this purpose, the development of polymeric solar cells has received a great deal of attention from both academic and industrial laboratories. [1][2][3] Indeed, the utilization of semiconducting conjugated polymers as active components in bulk heterojunction photovoltaic devices offers significant potential advantages over existing inorganic materials in terms of ease of processing, formation of large surface areas, and costs. For example, poly[2-methoxy-5-(3′,7′-dimethyloctyloxy)-p-phenylenevinylene] (MDMO-PPV), [4] regioregular poly(3-hexylthiophene) (P3HT), [5,6] and other polythiophene derivatives [7] have been extensively studied over the last decade, resulting in PCs with a power conversion efficiency between 3.0 and 5.0 %. However, the performances of these polymers are somehow restricted by their relatively large bandgap and the limited possibilities to modulate their physical properties by synthetic methods. New low-bandgap polymers have been developed over the years to better harvest the solar spectrum, especially in the 1.4-1.9 eV region. Promising copolymers based on fluorene units have been proposed by Andersson/Inganäs [8,9] and Cao, [10] with power conversion efficiencies between 2.0 and 2.8 %. Interestingly, the physical properties of polyfluorene derivatives can be easily modulated through the design of various alternating copolymers.[11] However, relatively low hole mobilities were reported for low-bandgap polyfluorene derivatives. Therefore, besides those recent advances, there is still a need for new polymeric materials to go beyond the 5 % efficiency of actual materials. [3,12,13] Along these lines, poly(N-vinylcarbazole) (PVK) is well known as an excellent photoconductor. [14,15] Furthermore, studies have demonstrated that PVK photoconduction increases when doped with sensitizers like 2,4,7-trinitrofluorenone (TNF) or C 60 . [15,16] In parallel, oligo-and poly(2,7-carbazole) derivatives have been successfully used in polymer lightemitting diodes (PLEDs) [17] and organic field-effect transistors (OFETs), [17,18] demonstrating good p-type transport properties. Recently, Müllen and co-workers [19] have reported solar cells with an efficiency of 0.6 % with poly(N-alkyl-2,7-carbazole), whereas Leclerc and co-workers [20] have shown an efficiency of 0.8 % with poly(2,7-carbazolenevinylene) derivatives. Moreover, in contrast with the fluorene unit the carbazole moiety is fully aromatic, providing a better chemical and environmental stability. Taking all of these results into account, the development of new low-bandgap copolymers based on carbazoles should therefore lead to interesting features for photovoltaic applications. However, poly(N-alkyl-2,7-carbazole)s generally exhibit poor solubilities and low molecular weights. [21] To solve these problems, bulky side chains are us...

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A Low‐Bandgap Poly(2,7‐Carbazole) Derivative for Use in High‐Performance Solar Cells

2007

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“…When an efficient synthetic route for achieving 2,7-dihalocarbazole derivatives was established [8,9], poly(2,7-carbazole)s emerged as an alternative to blue-light fluorescent polyfluorene derivatives, which possessed a photodegradation problem leading to a different color emission and optical instability [10,11]. Later, the conjugated copolymers of the electron-donating 2,7-carbazolylene and electron-accepting -systems were found to be very suitable as a p-type semiconductor for bulk heterojunction solar cells [12][13][14][15][16]. These findings stimulated renewed interests in the development of conjugated carbazole polymers with different connectivities.…”

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confidence: 99%

Synthesis and Properties of 1,8-Carbazole-Based Conjugated Copolymers

2010

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Abstract:A new series of conjugated carbazole polymers based on the 1,8-carbazolylene unit was synthesized by the Pd-catalyzed polycondensation between the 1,8-diiodocarbazole derivative and various bifunctional counter comonomers. An alkyne spacer was found to be a key to increasing the molecular weight of the resulting polymers. All the obtained polymers showed good solubilities in the common organic solvents, and they were fully characterized by Gel permeation chromatography (GPC), and 1 H NMR and infrared (IR) spectroscopies. The UV-vis absorption and fluorescence spectra revealed the relationship between the chemical structure and effective conjugation length. The efficiency order of the carbazole connectivity was 2,7-carbazolylene > 1,8-carbazolylene > 3,6-carbazolylene. The electrochemical properties of these polymers suggested the relatively facile oxidation at ca. +0.5-0.7 V vs. Fc/Fc + or a high potential as p-type semiconductors. The combination of the electrochemical oxidation potentials and the optical band gaps allowed us to estimate the HOMO and LUMO levels of the polymers. It was shown that the energy levels of the 1,8-carbazole-based conjugated polymers can be tunable by selecting the appropriate comonomer structures. OPEN ACCESSPolymers 2010, 2 160

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“…Namely, materials based on them are very promising because of their great stability, good solubility, excellent photoconductive properties, relatively intense luminescence, and good performance in OFETs, OLEDs, and thermoelectric materials [42][43][44][45][46][47][48][49][50][51][52]. Moreover, these compounds, and particularly halogenated carbazoles, are important synthetic intermediates and pharmacological targets [53].…”

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confidence: 99%

Two isostructural halogen derivatives of 9-ethylcarbazole: crystal structure, Hirshfeld surface analysis, and structural comparison with other simple analogs

et al. 2015

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This article describes a detailed study of the molecular packing and intermolecular interactions in crystals of two derivatives of 9-ethylcarbazole, i.e., 3-chloro-and 3-bromo-9-ethylcarbazole (1 and 2, respectively). A significance of this study lies both in the comparison drawn between the crystal structures of these compounds and those of several of their simple analogs [i.e., 3,6-dibromo-9-ethylcarbazole (3), 3,6-dibromo-9-methylcarbazole (4), 3,6-dibromocarbazole (5), 3-bromocarbazole (6), 3,6-diiodocarbazole (7), 9-ethylcarbazole (8), 9-methylcarbazole (9) and carbazole (10)], and in the preliminary assessment of their suitability as active materials for organic electronics. This comparison shows a close similarity in the packing of molecules of three of them (i.e., 3, 4, 6) that form the p-stacks along the shortest crystallographic axes, with a substantial spatial overlap between adjacent molecules in the stacks, depending mainly on the length of substituent at position 9 of carbazole skeleton and on the ratio of (%CÁÁÁH)/(%CÁÁÁC) interactions. Similar to them, in the crystal structures of 1 and 2 there is slipped face-to-face pÁÁÁp interaction, but in contrast this interaction connects two molecules of these compounds into the dimers that are further connected by C-HÁÁÁp interaction. The molecular packing in crystals of these compounds is intermediate between the arrangement of molecules of 3, 4, and 6, where the slipped p-stacking is predominant, and the typical herringbone packing in compounds 5 and 7-10. Thus, it can be supposed that out of ten compounds analyzed here, only 3, 4, and 6 will turn to be the most promising materials for device applications (particularly for field-effect transistors).

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Synthesis of 2,7-Carbazolenevinylene-Based Copolymers and Characterization of Their Photovoltaic Properties

Cited by 119 publications

References 40 publications

A Low‐Bandgap Poly(2,7‐Carbazole) Derivative for Use in High‐Performance Solar Cells

A Low‐Bandgap Poly(2,7‐Carbazole) Derivative for Use in High‐Performance Solar Cells

Synthesis and Properties of 1,8-Carbazole-Based Conjugated Copolymers

Two isostructural halogen derivatives of 9-ethylcarbazole: crystal structure, Hirshfeld surface analysis, and structural comparison with other simple analogs

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