Chain-Growth Polymerization of Unusual Anion-Radical Monomers Based on Naphthalene Diimide: A New Route to Well-Defined n-Type Conjugated Copolymers

Senkovskyy, Volodymyr; Tkachov, Roman; Komber, Hartmut; Sommer, Michael; Heuken, Maria; Voit, Brigitte; Huck, Wilhelm T. S.; Kataev, V.; Petr, Andreas; Kiriy, Anton

doi:10.1021/ja208710x

Cited by 128 publications

(129 citation statements)

References 37 publications

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“…Polymer Data and Film Preparation : Low molecular weight P(NDI2OD-T2) (P2a, P2b, P2c) was synthesized via catalyst transfer polymerization by Kiriy and coworkers, [ 36,37 ] high molecular weight P(NDI2OD-T2) (P1) was purchased from Polyera Corporation ("PolyeraActivInk N2200"). Molecular parameters and the melting points of the used samples are summarized in Table 1 and were obtained by size exclusion chromatography (SEC) in chloroform (P2a, P2b, P2c) and HT-SEC (160 °C) in trichlorobenzene (P1), both calibrated versus polystyrene, and differential scanning calorimetry (DSC), respectively.…”

Section: Methodsmentioning

confidence: 99%

“…Thereby, we studied commercially available P(NDI2OD-T2) purchased from Polyera Corporation ("PolyeraActivInk N2200") and referred to as P1, as well as three different batches of low molecular weight P(NDI2OD-T2) (denoted as P2a, P2b, P2c) synthesized via Ni-catalyzed chaingrowth polymerization. [ 36,37 ] Molecular parameters of the different batches used in this study are summarized in Table 1 . Films of around 25-100 nm thickness obtained by spin-coating from chlorobenzene were used as a starting point for the annealing experiments.…”

Section: Morphology Structure and Uv-vis Absorption In As-cast Filmsmentioning

confidence: 99%

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Charge Transport Anisotropy in Highly Oriented Thin Films of the Acceptor Polymer P(NDI2OD‐T2)

Tremel

Fischer

Kayunkid

et al. 2014

Advanced Energy Materials

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125

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cells today. While the majority of donoracceptor polymers are hole-conducting (p-type), [3][4][5] important progress has been achieved in the development of high performance, n-type polymeric semiconductors in recent years. [6][7][8] In 2009, Facchetti and co-workers introduced a novel n-type, donor-acceptor polymer, poly{[N,N′-bis(2-octyldodecyl)-1,4,5,8-naphthalenedicarboximide-2,6-diyl]-alt-5,5′-(2,2′-bithiophene)} P(NDI2OD-T2), which exhibits excellent electron mobilities as high as 0.85 cm 2 V −1 s −1 in top gate transistor devices under ambient conditions; [ 6 ] bulk-mobilities were found in the range of 5 × 10 −3 cm 2 V −1 s −1 for timeof-fl ight and electron-only current measurements. [ 9 ] Promising results have been further shown for all-polymer solar cells based on poly(3-hexylthiophene)s (P3HT) and P(NDI2OD-T2) as donor and acceptor, respectively, reaching power conversion effi ciencies of 1.4%. [ 10 ] Publications on P(NDI2OD-T2) initially focused on the chemistry, [ 7 ] charge transport and injection in multiple devices, [ 9,11,12 ] whereas little was reported about the structure of the semiconductor layer. While at fi rst it was assumed that P(NDI2OD-T2) forms mainly amorphous layers, [ 6 ] X-ray diffraction analysis and transmission electron microscopy (TEM) revealed the semicrystalline character of P(NDI2OD-T2) thin fi lms in recent years. [13][14][15][16][17] Rivnay et al. were the fi rst to show a remarkable degree of in-plane order in as-cast fi lms with an unconventional face-on texture in the bulk. [ 13 ] A striking texture change was observed upon melt-annealing, when the polymer chains undergo a transition from mainly face-on to edge-on. [ 15,18 ] A very recent study by Schuettfort et al. reports on a preferential edge-on texture at the top surface both for as-cast and melt-annealed layers. [ 16 ] Using mainly spectroscopic measurements, Steyrleuthner et al. demonstrated the strong tendency for aggregation not only in thin fi lms but also in solution, thereby identifying two different kinds of aggregates. [ 19 ] The precise stacking mode of the naphthalene diimide (NDI) and bithiophene (T2) units within the crystalline lattice was investigated via TEM by Brinkmann and coworkers [ 17 ] and Heeger and coworkers. [ 20 ] Highly oriented thin fi lms of P(NDI2OD-T2) were prepared by directional epitaxial crystallization (DEC) on 1,3,5-trichlorobenzene (TCB) and epitaxy on aligned fi lms of poly(tetrafl uoroethylene) (PTFE). Two polymorphs were identifi ed: i) in form I, the NDI and T2 which is up to 10 times higher than those perpendicular to the polymer chain.

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Section: Methodsmentioning

confidence: 99%

Section: Morphology Structure and Uv-vis Absorption In As-cast Filmsmentioning

confidence: 99%

Charge Transport Anisotropy in Highly Oriented Thin Films of the Acceptor Polymer P(NDI2OD‐T2)

Tremel

Fischer

Kayunkid

et al. 2014

Advanced Energy Materials

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125

244

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“…95 Metal-catalyzed polycondensations are also a potential method for synthesizing new n-type or specially functionalized materials. 90,96 Several recent synthetic approaches have focused upon increasing the solubility or dispersibility of conjugated polymers to enhance their processability. Side chains are essential for solubilizing conjugated polymers used in semiconducting applications, and similar concepts are applicable for electrochemical energy storage.…”

Section: Synthesismentioning

confidence: 99%

“…A major issue involves the lack of reliable synthetic methods to produce large quantities of n-type polymer. There are, however, new ways to make them using metal-catalyzed cross-couplings, 90,96 although these developments are very recent as of the time of this publication and have not been widely applied to electrode materials as of yet. There is one example, however, of an n-type polyfluorene stabilizing silicon nanoparticles in a composite anode.…”

Section: Other Conjugated Polymersmentioning

confidence: 99%

Recent advances in conjugated polymer energy storage

Mike

Lutkenhaus

2013

J Polym Sci B Polym Phys

190

152

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This review covers recent advances in conjugated polymers and their application in energy storage. Conjugated polymers are promising cost-effective, lightweight, and flexible electrode materials. The operating principles of conjugated polymers are presented within the framework of their potential for energy storage. Special focus is given to polyaniline electrodes. Recent advances are reviewed including new methods of synthesis, nanostructuring, and assembly. Also, covered are applications that take full advantage of the mechanical properties of conjugated polymers and future applications of these novel materials.

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“…The polymers containing naphthalene-diimide [13] or perylene-diimide [14], which show high electron mobility, were synthesized by Kiriy and coworkers by catalyst-transfer polymerization of the anion-radical monomer in the presence of the Pd or Ni catalyst. However, the obtained polymers possess high Đ values even though they acheive high enough MWs of the polymers.…”

Section: Introductionmentioning

confidence: 99%

Controlled Polymerization of Electron-deficient Naphthalene-diimide Containing Monomer by Negishi-type Catalyst-transfer Polymerization

Goto

Mori

Ueda

et al. 2015

J. Photopol. Sci. Technol.

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Negishi-type Catalyst-Transfer Polymerization (NCTP) of electron-deficient monomers has been attempted for the first time. Imide or ketone groups in such monomers show an excellent electron-deficient property. However, these functional groups cannot generally tolerate towad highly reactive Grignard reagents. In this work, we applied a zincate complex with lower basicity, t Bu 4 ZnLi 2 , for the polymerization of a naphthalene-diimide-containing monomer. Zinc-halogen exchange reaction was quantitatively conducted at 60 o C for 1 h without any protection of the imide group. Then, the polymerization was carried out by adding the Pd catalyst to afford an electron-deficient polymer, PTNDIT (M n = 8,400 and Ð = 1.35).

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Chain-Growth Polymerization of Unusual Anion-Radical Monomers Based on Naphthalene Diimide: A New Route to Well-Defined n-Type Conjugated Copolymers

Cited by 128 publications

References 37 publications

Charge Transport Anisotropy in Highly Oriented Thin Films of the Acceptor Polymer P(NDI2OD‐T2)

Charge Transport Anisotropy in Highly Oriented Thin Films of the Acceptor Polymer P(NDI2OD‐T2)

Recent advances in conjugated polymer energy storage

Controlled Polymerization of Electron-deficient Naphthalene-diimide Containing Monomer by Negishi-type Catalyst-transfer Polymerization

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