Poly(alkyl thiophene-3-carboxylates). Synthesis, properties and electroluminescence studies of a polythiophene with a carbonyl group attached to the ring

Pomerantz, M. A.; Yang, Chun‐Lei; Kasim, Ramesh K.; Elsenbaumer, Ronald L.

doi:10.1016/s0379-6779(97)80218-4

Cited by 19 publications

(15 citation statements)

References 8 publications

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“…The molecular weight M n of these materials was in the 4k region with PDIs around 2. Electroluminescence and bilayer devices were subsequently studied by Pomerantz et al [182] Efficiencies of 0.018 % were found in the ester PT polymers, which was much better than irregular poly(3-octylthiophene) (5 ´10 ±5 %) and regioregular poly(3-hexylthiophene) (1 ´10 ±4 %). [38] Poly(3-(2-(methacryloyloxy)ethyl)thiophene) (82) has been prepared by Holdcroft by the FeCl 3 method [18] (Fig.…”

Section: Carboxylic Acid Derivatives: Self-assembly and Sensorsmentioning

confidence: 99%

The Chemistry of Conducting Polythiophenes

McCullough¹

1998

Adv. Mater.

1,477

912

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Directing the structure and function of polythiophenes (PTs) can lead to remarkable enhancements in the electronic and photonic properties of the resultant materials, as discussed in this comprehensive review of the chemistry and synthesis of PTs. The Figure illustrates the use of heteroatom‐functionalized PTs as chemical sensors: upon ion complexation PT conjugation is greatly reduced, leading to a sensory response.

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Section: Carboxylic Acid Derivatives: Self-assembly and Sensorsmentioning

confidence: 99%

The Chemistry of Conducting Polythiophenes

McCullough¹

1998

Adv. Mater.

1,477

912

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“…1 H NMR defect analysis was performed for all of the entries in Table , with that for P3HET and P3EHET described below. Noonan and Pomerantz performed extensive NMR studies on P3HET allowing for the various defects to be quantified and the end groups to be assigned. ,− The potential triads, either HT–HT, TT–HT, HH–TT, or HT–HH, are shown in Figure C along with a representative expanded view of the aromatic region for P3HET in Figure A and P3EHET in Figure B. End groups with their expected values for chemical shifts are also provided in Figure C.…”

Section: Resultsmentioning

confidence: 99%

Influence of the Ester Directing Group on the Inhibition of Defect Formation in Polythiophenes with Direct Arylation Polymerization (DArP)

Pankow

Thompson

2020

Macromolecules

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Direct arylation polymerization (DArP) has allowed for the facile preparation of a variety of conjugated polymer architectures. Because DArP proceeds through a C−H activation pathway, the selectivity of only the desired C− H bond for certain monomers has remained a challenge. Low selectivity for the desired C−H bond can lead to the introduction of various structural defects. The development of conditions through the use of additives, screening and design of phosphine ligands, and precatalysts has provided condition sets that work for some monomers to afford the desired polymers with a minimization of defects. In addition to modifying the conditions, another handle for tuning the site selectivity for C−H activation is through the introduction of a directing group, such as an ester. Ester-functionalized conjugated polymers have gone through a renaissance of sorts where the inclusion of this functionality on thiophene-based monomers has garnered increased attention. To understand how this functionality can be exploited as a directing group for DArP, we study the formation of defects for poly(3-hexyl ester thiophene-2,5-diyl) (P3HET) and select structural analogues. We develop optimized conditions that allow for the synthesis of this polymer with improved molecular weight (M n ) (up to 15.9 kDa vs 11.7 kDa) and regioregularity (rr) (up to >99% vs 96%) in a shorter polymerization time (16 h vs 48 h). On the basis of extensive defect analysis using 1 H NMR spectroscopy, we rationally design a monomer for the synthesis of the donor−acceptor polymer poly(2hexyldecyl-[2,2′-bithiophene]-4-carboxylate-5,5′-diyl) (P3HDET-T) with good M n (26.2 kDa) and regioregularity (>99%). This study shows how the inclusion of ester directing groups and the formulation of pathways for defect formation can enable the rational design of monomers yielding conjugated polymers with improved M n and rr.

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“…Since the polymers with alkyl ester functional groups have been explored for various applications such as solar cells, − polymer light-emitting diodes (PLEDs), , and field-effect transistors (FETs), the optimization of the reaction conditions for 2b with alkyl ester functional groups has been also carried out (Table S1). The moderate HT regioregularity (∼90%, entries 2 and 4, Table S1) was obtained under the optimized conditions.…”

Section: Results and Discussionmentioning

confidence: 99%

A Direct C–H Coupling Method for Preparing π-Conjugated Functional Polymers with High Regioregularity

Zhang

Chang

et al. 2018

Macromolecules

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Highly regioregular conducting polymers such as poly(3-substituted thiophene)s (rrP3STs) are an important class of π-conjugated polymers that can be used in plastic electronic devices such as solar cells and field-effect transistors. But the current state of the art syntheses of rrP3STs all involve transition-metal-catalyzed cross-coupling of a heteroaryl halide or pseudohalide with a heteroaryl organometallic reagent. In this work, an efficient and mild method was developed using direct cross-coupling of sp 2 C−H bonds. More importantly, the method not only gave generally high regioregularity (up to 99%) but also can be applied for a series of substrate compounds with various structures and substituted groups. This should provide a general and direct way for the easy access to many functional/conducting polymers.

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Poly(alkyl thiophene-3-carboxylates). Synthesis, properties and electroluminescence studies of a polythiophene with a carbonyl group attached to the ring

Cited by 19 publications

References 8 publications

The Chemistry of Conducting Polythiophenes

The Chemistry of Conducting Polythiophenes

Influence of the Ester Directing Group on the Inhibition of Defect Formation in Polythiophenes with Direct Arylation Polymerization (DArP)

A Direct C–H Coupling Method for Preparing π-Conjugated Functional Polymers with High Regioregularity

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