Poly(3-dodecylthienylenevinylene)s: Regioregularity and Crystallinity

Zhang, Cheng; Sun, Jianyuan; Li, Rui; Sun, Sam-Shajing; Lafalce, Evan; Jiang, Xiran

doi:10.1021/ma200434v

Cited by 36 publications

(57 citation statements)

References 42 publications

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“…The optical excitation absorption cut off (corresponding to optical excitation energy gaps) are 560 nm (2.21 eV) for the donor (D) and 530 nm (2.34 eV) for the acceptor (A) blocks. Due to an intramolecular electronic push–pull interaction within the acceptor block repeat units, the absorption peak maximum of the acceptor block is at higher energy (around 420 nm) and has lower intensity compared to the donor block (peak maximum around 500 nm).…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and characterization of a novel c‐donor‐nc‐bridge‐c‐acceptor type block copolymer for optoelectronic applications

Sun

Nguyen

Zhang

2014

J. Polym. Sci. Part A: Polym. Chem.

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A novel conjugated block copolymer system containing a donor‐type conjugated block (c‐D) covalently connected to an acceptor type conjugated block (c‐A) via a nonconjugated and flexible bridge chain (nc‐B), also called a DBA type block copolymer, has been designed, synthesized, and characterized for potential cost‐effective and high‐efficiency optoelectronic applications such as solar cells. Specifically, D is a regio‐regular para‐2‐ethylhexyloxy‐substituted polyphenylenevinylene (or EH‐RO‐PPV), A is a regio‐regular polyphenylenevinylene with sulfone (SO2) acceptor moiety and a linear oxydecane (‐OC10H21) group substituted on every phenylene unit, and B contains an aliphatic chain with two or four methylene units. The size of each block can be controlled via synthetic feed ratio of the monomer and the terminator. The measured average molecular weights of D, A, and DBA based on gel permission chromatography are in good agreements with the molecular weights calculated using the monomer:terminator synthetic feed ratios. Preliminary optoelectronic device studies revealed an order of magnitude better improvement in photoelectric power conversion efficiency of DBA over the corresponding D/A blend under identical fabrication and testing conditions. Such improvements could be attributed to more efficient photo induced charge separation and charge transport in DBA versus in D/A blends. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1149–1160

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, and characterization of a novel c‐donor‐nc‐bridge‐c‐acceptor type block copolymer for optoelectronic applications

Sun

Nguyen

Zhang

2014

J. Polym. Sci. Part A: Polym. Chem.

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“…For instance, introduction of non-polar or polar functionalities via copolymerization or post-functionalization like alkyl, halogen, cyano, phenyl, hydroxyl, and carboxyl, would endow polymers with unique properties such as crystallinity, flexibility, flame retardancy, chemical resistance, impact strength, processability and adhesion [1e8]. Also, some special ethylene-based functional materials like ionomers [9,10], poly (thienylene vinylene)s (PTVs) [11], and polymer light emitting diodes (PLEDs) [12,13] received considerable attention in recent years for their potential application as electroactive materials. However, ethylene-co-aryl ether polymers have been rarely reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of precisely-defined ethylene-co-aryl ether polymers via ADMET polymerization

Song

Miao

Wang

et al. 2015

Polymer

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“…the proportion of head‐to‐tail (HT) coupling between monomer units in the polymer backbone) leads to a decrease in film crystallinity, hole mobility, and hence device performance 2b. 3 In contrast, for poly(3‐hexyl‐2,5‐thienylene vinylene) (P3HTV) (Scheme ), the variation in regioregularity does not result in apparent differences in film crystallinity or device function 2e,f. The major difference in the chemical structures between P3HT and P3HTV lies in the vinyl unit between the adjacent thiophene rings, which serves to increase the distance between the alkyl side chains therefore decreasing the distribution density of the alkyl side chains along the polymer backbone.…”

Section: Introductionmentioning

confidence: 99%

Effect of the Side‐Chain‐Distribution Density on the Single‐Conjugated‐Polymer‐Chain Conformation

Adachi

Lee

et al. 2013

ChemPhysChem

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The spatial arrangement of the side chains of conjugated polymer backbones has critical effects on the morphology and electronic and photophysical properties of the corresponding bulk films. The effect of the side-chain-distribution density on the conformation at the isolated single-polymer-chain level was investigated with regiorandom (rra-) poly(3-hexylthiophene) (P3HT) and poly(3-hexyl-2,5-thienylene vinylene) (P3HTV). Although pure P3HTV films are known to have low fluorescence quantum efficiencies, we observed a considerable increase in fluorescence intensity by dispersing P3HTV in poly(methyl methacrylate) (PMMA), which enabled a single-molecule spectroscopy investigation. With single-molecule fluorescence excitation polarization spectroscopy, we found that rra-P3HTV single molecules form highly ordered conformations. In contrast, rra-P3HT single molecules, display a wide variety of different conformations from isotropic to highly ordered, were observed. The experimental results are supported by extensive molecular dynamics simulations, which reveal that the reduced side-chain-distribution density, that is, the spaced-out side-chain substitution pattern, in rra-P3HTV favors more ordered conformations compared to rra-P3HT. Our results demonstrate that the distribution of side chains strongly affects the polymer-chain conformation, even at the single-molecule level, an aspect that has important implications when interpreting the macroscopic interchain packing structure exhibited by bulk polymer films.

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Poly(3-dodecylthienylenevinylene)s: Regioregularity and Crystallinity

Cited by 36 publications

References 42 publications

Design, synthesis, and characterization of a novel c‐donor‐nc‐bridge‐c‐acceptor type block copolymer for optoelectronic applications

Design, synthesis, and characterization of a novel c‐donor‐nc‐bridge‐c‐acceptor type block copolymer for optoelectronic applications

Synthesis and characterization of precisely-defined ethylene-co-aryl ether polymers via ADMET polymerization

Effect of the Side‐Chain‐Distribution Density on the Single‐Conjugated‐Polymer‐Chain Conformation

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