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Synthesis and Application of Conjugated Polymers

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A special issue of Polymers (ISSN 2073-4360).

Deadline for manuscript submissions: closed (12 December 2018) | Viewed by 59094

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Special Issue Editor

Prof. Dr. Toshiki Aoki

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Department of Chemistry and Chemical Engineering, Graduate School of Science and Technology, Niigata University, Ikarashi 2-8050, Nishi-Ku, Niigata 950-2181, Japan
Interests: functional polymer; permselective membranes; polymer chemistry; polymerization; asymmetric polymerization; optical resolution
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Special Issue Information

Dear Colleagues,

The function of polymer materials can be controlled by their molecular structures. Since commercially-available polymers are usually based on a single bond main chain, i.e., an aliphatic backbone, such as polyethylene and nylon, their backbones are relatively flexible and irregular and they are not electrically conductive. On the other hand, since conjugated polymers, such as poly(substituted acetylene)s and poly(aryleneethynylene)s, contain a double-bond and aromatic main chain, they are rigid, regular and tend to form stacking structures, and they can be electrically active. Many kinds of new conjugated polymers have been synthesized and unique properties of conjugated polymers have been reported. However, discussion about the relationships between their molecular structures and properties and functions were not enough. Therefore, this Special Issue invites original research about precise synthesis, characterization, and/or unique application of conjugated polymers including supramolecular conjugation structures based on staking structures and inorganic conjugate polymers like polysilanes. Both original articles and reviews are welcome.

Prof. Toshiki AOKI
Guest Editor

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Keywords

Synthesis
Conjugated polymers
Acetylene polymer
Ethynylene polymer
Conjugated supramolecular polymers
Membrane separation
Silicon-containing polymers
Stacking polymers
Helical structures
Chiral structures

Published Papers (14 papers)

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Research

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22 pages, 3318 KiB

Open AccessArticle

Impact of Side Chains of Conjugated Polymers on Electronic Structure: A Case Study

by Clemens Matt, Florian Lombeck, Michael Sommer and Till Biskup

Polymers 2019, 11(5), 870; https://doi.org/10.3390/polym11050870 - 13 May 2019

Cited by 6 | Viewed by 3192

Abstract

Processing from solution is a crucial aspect of organic semiconductors, as it is at the heart of the promise of easy and inexpensive manufacturing of devices. Introducing alkyl side chains is an approach often used to increase solubility and enhance miscibility in blends. The influence of these side chains on the electronic structure, although highly important for a detailed understanding of the structure-function relationship of these materials, is still barely understood. Here, we use time-resolved electron paramagnetic resonance spectroscopy with its molecular resolution to investigate the role of alkyl side chains on the polymer PCDTBT and a series of its building blocks with increasing length. Comparing our results to the non-hexylated compounds allows us to distinguish four different factors determining exciton delocalization. Detailed quantum-chemical calculations (DFT) allows us to further interpret our spectroscopic data and to relate our findings to the molecular geometry. Alkylation generally leads to more localized excitons, most prominent only for the polymer. Furthermore, singlet excitons are more delocalized than the corresponding triplet excitons, despite the larger dihedral angles within the backbone found for the singlet-state geometries. Our results show TREPR spectroscopy of triplet excitons to be well suited for investigating crucial aspects of the structure-function relationship of conjugated polymers used as organic semiconductors on a molecular basis. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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11 pages, 1969 KiB

Open AccessArticle

Helix-Sense-Selective Polymerization of Phenylacetylenes Having a Porphyrin and a Zinc-Porphyrin Group: One-Handed Helical Arrangement of Porphyrin Pendants

by Masahiro Teraguchi, Nobuyuki Nahata, Takahiro Nishimura, Toshiki Aoki and Takashi Kaneko

Polymers 2019, 11(2), 274; https://doi.org/10.3390/polym11020274 - 06 Feb 2019

Cited by 3 | Viewed by 3341

Abstract

Newly synthesized two kinds of achiral phenylacetylenes having a free-base- or a zinc-porphyrin (1 and Zn1, respectively) were polymerized by using a chiral rhodium catalyst system, Rh⁺(nbd)[(η⁶-C₆H₅)B^–(C₆H₅)₃] catalyst and (R)-(+)- or (S)-(–)-1-phenylethylamine ((R)- or (S)-PEA, respectively) cocatalyst. Poly(1) and poly(Zn1) in THF showed a Cotton signal at the absorption region of the porphyrin and the main chain in the circular dichroism (CD) spectra. This result suggests that poly(1) and poly(Zn1) exist in a conformation with an excess of one-handed helix sense and the porphyrin moiety arranged in chiral helical fashion. The one-handed helical structure of poly(1) could be sustained in a mixture of THF/HMPA (10/2, v/v) due to stabilizing by stacking effect of porphyrin moieties along the main chain. This is the first example about helix-sense-selective polymerization by using Rh⁺(nbd)[(η⁶-C₆H₅)B^–(C₆H₅)₃] catalyst. Additionally, poly(Zn1) showed about 10 times larger CD intensity in comparison with poly(1). This result suggests the regularity of arrangement of the porphyrin in poly(Zn1) is higher compared with poly(1). Spatial arrangement of porphyrins was achieved by utilizing a one-handed helical poly(phenylacetylenes) as a template. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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11 pages, 2533 KiB

Open AccessArticle

Fabrication and Application of Dual-Modality Polymer Nanoparticles Based on an Aggregation-Induced Emission-Active Fluorescent Molecule and Magnetic Fe₃O₄

by Lingyun Wang, Meiying Huang, Hao Tang, Derong Cao and Yu Zhao

Polymers 2019, 11(2), 220; https://doi.org/10.3390/polym11020220 - 28 Jan 2019

Cited by 10 | Viewed by 3558

Abstract

Fluorescent magnetic nanoparticles (NPs) utilized for imaging hold great promise for biomedical applications, but it remains a challenging task. Here, we report novel dual-modality NPs using an aggregation-induced emission (AIE)-active and near-infrared (NIR) emissive dye (TPAS) and magnetic Fe₃O₄ as the core, and biocompatible polymer Pluronic F-127 as the encapsulation matrix by self-assembly procedures. The obtained fluorescent-magnetic AIE NPs have both high fluorescence quantum yield (13.8%) at 700 nm and high magnetic saturation value. With good photostability and biocompatibility, the resulting NPs show effective MRI ability, but also a stain in cytoplasm with a strong NIR fluorescent signal. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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10 pages, 2034 KiB

Open AccessCommunication

Use of Grafted Voltage Stabilizer to Enhance Dielectric Strength of Cross-Linked Polyethylene

by Wei Dong, Xuan Wang, Bo Tian, Yuguang Liu, Zaixing Jiang, Zhigang Li and Wei Zhou

Polymers 2019, 11(1), 176; https://doi.org/10.3390/polym11010176 - 20 Jan 2019

Cited by 24 | Viewed by 4201

Abstract

Aromatic voltage stabilizers can improve the dielectric properties of cross-linked polyethylene (XLPE); however, their poor compatibility with XLPE hinders their practical application. Improving the compatibility of aromatic voltage stabilizers with XLPE has, therefore, become a new research goal. Herein 1-(4-vinyloxy)phenylethenone (VPE) was prepared and characterized. It can be grafted onto polyethylene molecules during the cross-linking processes to promote stability of the aromatic voltage stabilizers in XLPE. Fourier transform infrared spectroscopy confirmed that VPE was successfully grafted onto XLPE, and effectively inhibited thermal migration. Thermogravimetric analysis showed that the grafted VPE/XLPE composite exhibits a better thermal stability than a VPE/PE blend composite. Evaluation of the electrical properties showed that the breakdown strength and electrical tree initiation voltage of the VPE/XLPE composite were increased by 15.5% and 39.6%, respectively, when compared to those of bare XLPE. After thermal aging, the breakdown strength and electrical tree initiation voltage of the VPE/XLPE composite were increased by 9.4% and 25.8%, respectively, in comparison to those of bare XLPE, which indicates that the grafted voltage stabilizer can effectively inhibit its migration and enhance the stability of the composite material. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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11 pages, 5212 KiB

Open AccessEditor’s ChoiceArticle

Improving the Performances of Perovskite Solar Cells via Modification of Electron Transport Layer

by Mao Jiang, Qiaoli Niu, Xiao Tang, Heyi Zhang, Haowen Xu, Wentao Huang, Jizhong Yao, Buyi Yan and Ruidong Xia

Polymers 2019, 11(1), 147; https://doi.org/10.3390/polym11010147 - 16 Jan 2019

Cited by 32 | Viewed by 6120

Abstract

The commonly used electron transport material (6,6)-phenyl-C61 butyric acid methyl ester (PCBM) for perovskite solar cells (PSC) with inverted planar structures suffers from properties such as poor film-forming. In this manuscript, we demonstrate a simple method to improve the film-forming properties of PCBM by doping PCBM with poly(9,9-dioctylfluorene-co-benzothiadiazole) (F8BT) as the electron transport layer (ETL), which effectively enhances the performance of CH₃NH₃PbI₃ based solar cells. With 5 wt % F8BT in PCBM, the short circuit current (J_SC) and fill factor (FF) of PSC both significantly increased from 17.21 ± 0.15 mA·cm⁻² and 71.1 ± 0.07% to 19.28 ± 0.22 mA·cm⁻² and 74.7 ± 0.21%, respectively, which led to a power conversion efficiency (PCE) improvement from 12.6 ± 0.24% to 15 ± 0.26%. The morphology investigation suggested that doping with F8BT facilitated the formation of a smooth and uniform ETL, which was favorable for the separation of electron-hole pairs, and therefore, an improved performance of PSC. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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10 pages, 3579 KiB

Open AccessArticle

Characterization of Solvent-Treated PEDOT:PSS Thin Films with Enhanced Conductivities

by Syang-Peng Rwei, Yi-Huan Lee, Jia-Wei Shiu, Ragu Sasikumar and Uin-Ting Shyr

Polymers 2019, 11(1), 134; https://doi.org/10.3390/polym11010134 - 14 Jan 2019

Cited by 46 | Viewed by 8770

Abstract

The conducting polymer of poly(3,4-ethylenedioxythiophene):poly(4-styrenesulfonate) (PEDOT:PSS) is one of the most important and intensively investigated organic conducting materials. The PEDOT:PSS water dispersions with various concentrations of poly (4-styrenesulfonic acid) solution (PSSAS) were synthesized by 3,4-ethylenedioxythiophene (EDOT) in the presence of water. The fabrication of the solvent-treated PEDOT:PSS films through spin coating and solvent treatment processes was achieved with a solvent of pure water mixed with acetone (or MeOH, EtOH) in a ratio of 50:50. Moreover, both the organic solvent and water have synergetic effects while the PSS and PEDOT-attached PSS segments will form a coil-like and a linear (or extended-coil) structure, respectively. That may induce a stacking of the linear and planar PEDOT-attached PSS segments, which favors the formation of a crystalline phase. Finally, the maximum electrical conductivity of the PEDOT:PSS thin films with solvent treatment was investigated by means of X-ray diffraction (XRD) patterns and scanning electron microscope (SEM) images. Furthermore, we aimed to explain the synergetic effects of phase separation of the PEDOT:PSS thin films by both the organic solvent and water. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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13 pages, 3670 KiB

Open AccessArticle

Methoxy-Group Control of Helical Pitch in Stereoregular Poly(2-ethynylmethoxynaphthalene) Prepared by Rhodium Complex Catalyst

by Yasuteru Mawatari, Yoshiaki Yoshida, Kai Huang and Masayoshi Tabata

Polymers 2019, 11(1), 94; https://doi.org/10.3390/polym11010094 - 08 Jan 2019

Cited by 2 | Viewed by 3979

Abstract

The position of the methoxy group in a poly(n-methoxy-2-ethynylnaphthalene) (PnMeO2EN) was found to control the helical pitch of the π-conjugated polymer in the solid state. These PnMeO2ENs were stereoregularly synthesized using an Rh-complex catalyst in ethanol or toluene as the solvent. The helical structure in the solid phase was confirmed by conventional analytical methods, namely diffuse reflective ultraviolet–visible light (UV–Vis) and Raman spectroscopies, X-ray diffraction, and ¹³C cross-polarization magic angle spinning NMR spectroscopy, together with molecular mechanics calculations, because the as obtained polymers were insoluble in common solvents. The color of poly(6-methoxy-2-ethynylnaphthalene) (P6MeO2EN) (yellow or red) depended on the polymerization solvent, whereas no such dependency was observed for the yellow-colored P7MeO2EN and P8MeO2EN. The helical structures energetically optimized by molecular mechanics indicate that the red- and yellow-colored P6MeO2ENs form contracted and stretched helices, respectively. Due to the relatively unconstrained rotations of the 6-methoxynaphthyl moieties, the methoxy groups in P6MeO2EN are less sterically hindered along the helical axis. On the contrary, P7MeO2EN and P8MeO2EN have stretched helices due to the considerable steric hindrance imparted by their methoxy groups. The thermal cis-to-trans isomerization of P6MeO2EN in the contracted-helix form required a somewhat higher temperature than that of the stretched helix. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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11 pages, 1978 KiB

Open AccessArticle

Proposed Mechanism for the High-Yield Polymerization of Oxyethyl Propiolates with Rh Complex Catalyst Using the Density Functional Theory Method

by Yoshiaki Yoshida, Yasuteru Mawatari and Masayoshi Tabata

Polymers 2019, 11(1), 93; https://doi.org/10.3390/polym11010093 - 08 Jan 2019

Cited by 6 | Viewed by 2846

Abstract

In this study, poly(oxyethyl propiolate)s (POP)s featuring various oxyethylene derivatives are synthesized using a [Rh(norbornadiene)Cl]₂ catalyst. In particular, POPs featuring the normal oxyethylene chain in the side-chain exhibit excellent yields and high molecular weights in methanol and N,N-dimethylformamide at 40 °C, compared with poly(n-alkyl propiolate)s (PnAP)s. The high reactivity of the oxyethyl propiolate (OP) monomers is clarified by considering the time dependences of the polymerization yields of OPs and alkyl propiolates (Aps). Furthermore, the monomer structure and intermediate conformation of the Rh complex are optimized using Density Function theory (DFT) methods (B3LYP/6-31G** and B3LYP/LANL2DZ) and a polymerization mechanism is proposed. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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11 pages, 1639 KiB

Open AccessArticle

Synthesis of Bithiophene-Based D-A₁-D-A₂ Terpolymers with Different A₂ Moieties for Polymer Solar Cells via Direct Arylation

by Jinfeng Huang, Zhenkun Lin, Wenhuai Feng and Wen Wang

Polymers 2019, 11(1), 55; https://doi.org/10.3390/polym11010055 - 02 Jan 2019

Cited by 9 | Viewed by 3395

Abstract

A series of bithiophene (2T)-based D-A₁-D-A₂ terpolymers with different A₂ moieties were prepared via direct arylation reaction. In these terpolymers, pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) was selected as the first electron-accepting (A₁) moiety, 2,1,3-benzothiadiazole (BT) or fluorinated benzothiadiazole (FBT) or octyl-thieno[3,4-c]pyrrole-4,6-dione (TPD) or 2,1,3-benzoselendiazole (SeT) was selected as the second electron-accepting (A₂) moiety, while bithiophene with hexyl side chain was used as the electron-donating moiety. The UV-vis absorption, electrochemical properties, blend film morphology, and photovoltaic properties were studied to explore the effects of the A₂ moiety. It is shown that these terpolymer films exhibit broad absorption (350–1000 nm), full width at half-maximum of more than 265 nm and ordered molecular packing. Varying the A₂ moiety could affect the energy levels and blend film morphology leading to different polymer solar cell (PSC) performances of these (2T)-based D-A₁-D-A₂ terpolymers. As a result, the highest J_sc of 10.70 mA/cm² is achieved for Polymer 1 (P1) with BT as A₂ moiety, while the higher highest occupied molecular orbital (HOMO) level limits the open circuit voltage (V_oc) and leads to a power conversion efficiency (PCE) of 3.46%. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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8 pages, 901 KiB

Open AccessArticle

Optical, Electrical and Thermal Properties of Organic–Inorganic Hybrids with Conjugated Polymers Based on POSS Having Heterogeneous Substituents

by Kazunari Ueda, Kazuo Tanaka and Yoshiki Chujo

Polymers 2019, 11(1), 44; https://doi.org/10.3390/polym11010044 - 29 Dec 2018

Cited by 15 | Viewed by 2918

Abstract

Preparation of organic–inorganic hybrids with conventional conjugated polymers such as polyfluorene (PF) and poly(3-hexylthiophene) (P3HT) were demonstrated via the facile blending in solution by employing polyhedral oligomeric silsesquioxane (POSS) having heterogeneous alkyl substituents. From the optical measurements, it was shown that the modified POSS derivatives played a critical role in facilitating amorphous state of polymer matrices. Interestingly, although inter-strand interaction decreased after POSS addition in the hybrid films, thermal stability can be enhanced in the presence of the modified POSS with long alkyl chains. Furthermore, it was demonstrated that carrier mobilities through the hybrid film was minimally reduced by POSS. These results suggest that POSS should be a versatile building block to form hybrid with various types of polymers for enhancing durability without loss of electronic properties of organic components. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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15 pages, 3548 KiB

Open AccessArticle

Single Local Injection of Epigallocatechin Gallate-Modified Gelatin Attenuates Bone Resorption and Orthodontic Tooth Movement in Mice

by Yuta Katsumata, Hiroyuki Kanzaki, Yoshitomo Honda, Tomonari Tanaka, Yuuki Yamaguchi, Kanako Itohiya, Sari Fukaya, Yutaka Miyamoto, Tsuyoshi Narimiya, Satoshi Wada and Yoshiki Nakamura

Polymers 2018, 10(12), 1384; https://doi.org/10.3390/polym10121384 - 13 Dec 2018

Cited by 19 | Viewed by 3493

Abstract

Osteoclastic bone resorption enables orthodontic tooth movement (OTM) in orthodontic treatment. Previously, we demonstrated that local epigallocatechin gallate (EGCG) injection successfully slowed the rate of OTM; however, repeat injections were required. In the present study, we produced a liquid form of EGCG-modified gelatin (EGCG-GL) and examined the properties of EGCG-GL with respect to prolonging EGCG release, NF-E2-related factor 2 (Nrf2) activation, osteoclastogenesis inhibition, bone destruction, and OTM. We found EGCG-GL both prolonged the release of EGCG and induced the expression of antioxidant enzyme genes, such as heme oxygenase 1 (Hmox1) and glutamate-cysteine ligase (Gclc), in the mouse macrophage cell line, RAW264.7. EGCG-GL attenuated intracellular reactive oxygen species (ROS) levels were induced by the receptor activator of nuclear factor-kB ligand (RANKL) and inhibited RANKL-mediated osteoclastogenesis in vitro. An animal model of bone destruction, induced by repeat Lipopolysaccharide (LPS)-injections into the calvaria of male BALB/c mice, revealed that a single injection of EGCG-GL on day-1 could successfully inhibit LPS-mediated bone destruction. Additionally, experimental OTM of maxillary first molars in male mice was attenuated by a single EGCG-GL injection on day-1. In conclusion, EGCG-GL prolongs the release of EGCG and inhibits osteoclastogenesis via the attenuation of intracellular ROS signaling through the increased expression of antioxidant enzymes. These results indicate EGCG-GL would be a beneficial therapeutic approach both in destructive bone disease and in controlling alveolar bone metabolism. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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10 pages, 2159 KiB

Open AccessArticle

[Rh(L-alaninate)(1,5-Cyclooctadiene)] Catalyzed Helix-Sense-Selective Polymerizations of Achiral Phenylacetylenes

by Qingyu Wang, Hongge Jia, Yongqiang Shi, Liqun Ma, Guoxing Yang, Yazhen Wang, Shuangping Xu, Jianjun Wang, Yu Zang and Toshiki Aoki

Polymers 2018, 10(11), 1223; https://doi.org/10.3390/polym10111223 - 03 Nov 2018

Cited by 5 | Viewed by 3982

Abstract

The [Rh(L-alaninate)(cod)] (cod = 1,5-Cyclooctadiene) complex was synthesized and characterized. Asymmetric polymerizations of achiral phenylacetylene with two hydroxyl groups and a dodecyl group (DoDHPA) were performed by using the rhodium complex as the catalyst to provide polymers with a higher molecular weight (>10⁵) than the polymers obtained using the [Rh(cod)Cl]₂ initiator systems. The resulting polymers showed circular dichroism (CD) signals at approximately 310 and 470 nm, indicating that they have a preferential one-handed helical structure. The helix sense in the polymer main chain was controlled by the sign of the catalyst chirality. These findings suggest that the rhodium complex with a chiral amine is the true active species for the helix-sense-selective polymerization of DoDHPA. The [Rh(L-alaninate)(cod)] complex also exhibits high catalytic activity in the polymerization of phenylacetylene (PA) to give a high yield and molecular weight. All these results demonstrate that this Rh complex is an excellent catalyst for the polymerization of phenylacetylene monomers. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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11 pages, 6211 KiB

Open AccessArticle

Synthesis and Characterization of Fully Conjugated Ladder Naphthalene Bisimide Copolymers

by Feng Liu, Yonggang Wu, Chao Wang, Junshu Ma, Fan Wu, Ye Zhang and Xinwu Ba

Polymers 2018, 10(7), 790; https://doi.org/10.3390/polym10070790 - 18 Jul 2018

Cited by 7 | Viewed by 4280

Abstract

Fully conjugated ladder copolymers have attracted considerable attention due to their unique fused-ring structure and optoelectronic properties. In this study, two fully conjugated ladder naphthalene diimide (NDI) copolymers, P(NDI-CZL) and P(NDI-TTL) with imine-bridged structures are presented in high yields. Both of the two copolymers have good solubility and high thermal stability. The corresponding compounds with the same structure as the copolymers were synthesized as model system. The yields for each step of the synthesis of the model compounds are higher than 95%. These results suggest that P(NDI-CZL) and P(NDI-TTL) can be synthesized successfully with fewer structural defects. The structures and optoelectronic properties of compounds and copolymers are investigated by NMR, fourier transform infrared spectroscopy (FTIR), ultraviolet-visible spectroscopy (UV-vis), and cyclic voltammetry (CV). Both in solution and as a thin film, the two copolymers show two UV-vis absorption bands (around 300–400 nm and 400–750 nm) and a very weak fluorescence. The collective results suggest that the two fully conjugated ladder copolymers can be used as potential acceptor materials. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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Review

Jump to: Research

24 pages, 5082 KiB

Open AccessReview

Some Important Issues of the Commercial Production of 1-D Nano-PANI

by Ying Wu, Jixiao Wang, Bin Ou, Song Zhao and Zhi Wang

Polymers 2019, 11(4), 681; https://doi.org/10.3390/polym11040681 - 15 Apr 2019

Cited by 13 | Viewed by 3881

Abstract

One-dimensional polyaniline nano-materials (1-D nano-PANI) have great promise applications in supercapacitors, sensors and actuators, electrochromic devices, anticorrosive coatings, and other nanometer devices. Consequently, commercial production of 1-D nano-PANI at large-scale needs to be quickly developed to ensure widespread usage of this material. Until now, approaches—including hard template methods, soft template methods, interfacial polymerization, rapid mixing polymerization, dilute polymerization, and electrochemical polymerization—have been reported to be used to preparation of this material. Herein, some important issues dealing with commercial production of 1-D nano-PANI are proposed based on the complexity of the synthetic process, its characters, and the aspects of waste production and treatment in particular. In addition, potential solutions to these important issues are also proposed. Full article

(This article belongs to the Special Issue Synthesis and Application of Conjugated Polymers)

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