Facile synthesis of high refractive index thiophene‐containing polystyrenes

An, Young Chul; Konishi, Gen‐ichi

doi:10.1002/app.35077

Cited by 16 publications

(5 citation statements)

References 65 publications

(59 reference statements)

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“…A variety of highly refractive vinyl polymers with functional side chains has been developed, which include poly(methacrylate)s with alkyl sulfides ( n = 1.624–1.725), acrylate polymers with tetraphenylethane skeletons ( n = 1.60), and selenide-containing poly(methacrylate)s ( n = 1.599–1.719) . Several styrene-based high-refractive-index polymers have also been investigated. − Nevertheless, these methacrylate-based polymers exhibit unsatisfactory refractive indices owing to the presence of carbonyl groups with low molar refractions, whereas styrene-based polymers generally have the inherent drawback of insufficient transparency that is also time-dependent. Therefore, the development of a new methodology that affords high-refractive-index polymers with excellent transparencies, tunable low T g values, reasonable Abbe’s numbers, and good thermal properties remains a challenge.…”

Section: Introductionmentioning

confidence: 99%

Highly Transparent Benzothiazole-Based Block and Random Copolymers with High Refractive Indices by RAFT Polymerization

Sato

Sobu

Nakabayashi

et al. 2020

ACS Appl. Polym. Mater.

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The development of thermally stable, highly transparent polymers with superior refractive indices and Abbe's numbers are important for the further development of next-generation technology such as miniaturized opto-integrated devices and advanced lenses. Highly transparent benzothiazole-based copolymers having either block or random sequences and high refractive indices were synthesized by reversible addition−fragmentation chain transfer (RAFT) polymerization. The conventional free-radical and RAFT copolymerizations of 2-benzothiazolyl vinyl sulfide (BTVS) and 2-vinylnaphthalene (VNA) produced random copolymers with adjustable BTVS contents between 8 and 54%. Chain extending the macrochain transfer agent, which was prepared by the RAFT polymerization of BTVS, with VNA was well-controlled, enabling the synthesis of block copolymers with high BTVS contents (up to 70%) and reasonable polymer yields (up to 60%). The benzothiazole-based homopolymer, poly(BTVS), exhibited a high refractive index (1.7432) and a reasonable Abbe's number (17.0). Excellent transmittances (>93%) of 400 nm light were observed for both copolymers composed of BTVS and VNA, and high refractive indices of 1.7178−1.6672 were achieved. The resulting benzothiazole-based copolymers exhibited high refractive indices (>1.7), high transparencies, tunable low glass-transition temperatures (T g = 75−150 °C), and high thermal stabilities (T d5 > 240 °C) by adjusting the chemical structure, composition, and sequence of the comonomer. This report presents development of the first high-refractive-index polymers derived from S-vinyl sulfide derivatives with benzothiazole side chains, exhibiting the synergistic effects of combining aromatic naphthalene and heteroaromatic benzothiazole units.

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Section: Introductionmentioning

confidence: 99%

Highly Transparent Benzothiazole-Based Block and Random Copolymers with High Refractive Indices by RAFT Polymerization

Sato

Sobu

Nakabayashi

et al. 2020

ACS Appl. Polym. Mater.

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“…One strategy to improve the refractive index of organic polymers is to introduce some polarizable main group heteroatoms, particularly sulfur, to the polymer chains. Therefore, some polymers containing thioether, , thianthrene, sulfone, , or thiophene groups were well investigated and exhibited refractive indices between 1.6 and 1.8. In this work, sulfur atoms were introduced to the repeat units through the efficient thiol–ene coupling reaction.…”

Section: Results and Discussionmentioning

confidence: 99%

Intrinsic High Refractive Index Siloxane–Sulfide Polymer Networks Having High Thermostability and Transmittance via Thiol–Ene Cross-Linking Reaction

Chen¹,

Fang²,

Wang³

et al. 2018

Macromolecules

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Siloxane-based polymer films obtained by the sol−gel process are often porous and exhibit low refractive indices. To address this issue, we have prepared two intrinsic high refractive index siloxane− sulfide polymer networks via the Piers−Rubinsztajn reaction and thiol− ene click chemistry based on readily available tetraethoxysilane (TEOS). Our siloxane−sulfide polymers consisting of aromatic groups and sulfur display enhanced thermostability with high T g (>120 °C) and T 5d (>320 °C) as compared to related materials. Such good thermal properties significantly expand their application as high thermostable optical materials. Besides, both flexible and colorless polymer films P1 and P2 exhibit high refractive indices of 1.625 and 1.665 at 546 nm, respectively. P2 also shows high refractive index of 1.648 at 1000 nm. Moreover, both siloxane−sulfide polymer films are uniform and homogeneous with high optical transmittance of 90% for wavelength ranging from 400 to 2000 nm. These data indicate that the new siloxane−sulfide polymers have potential application as optical materials such as antireflective coatings, encapsulation resin for the fabrication of LED, and the infrared transmitting materials.

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“…[25] Therefore, triazines, [26][27][28] pyridazines, [29] and pyrimidines, [29][30][31] which contain ─C═N─C─ bonds, have been employed as efficient units in main-chain-type polymers to enhance their refractive indices. Moreover, polymethacrylates and polystyrenes with carbazole, [32,33] thiophene, [34,35] and thiadiazole [1] side chains have been developed. High-refractive-index polymers have also been prepared from thiadiazole-containing diacrylates for applications in thermal nanoimprint lithography.…”

Section: Introductionmentioning

confidence: 99%

High Refractive Index Copolymers from Aromatic Heterocycle‐Based Vinyl Sulfides and Phthalimide/Maleimide Derivatives

Watanabe,

Morikawa,

Samitsu

et al. 2023

Macro Chemistry & Physics

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Herein, we present the rational design and facile synthesis of high‐refractive‐index copolymers with good optical transparency and tunable thermal stability using aromatic heterocycle‐based vinyl sulfides via conventional radical copolymerization. 2‐Thiazolylvinylsulfide (2TVS), 1,3,4‐thiadiazolylvinylsulfide (1,3,4‐TVS), 3‐methylimidazolylvinylsulfide (3MIVS), and 5‐methlthio‐1,3,4‐thiadiazolylvinylsulfide (MeSTVS) were selected to enhance the refractive index, and N‐vinylphthalimide (NVPI) and N‐phenylmaleimide (NPMI) were chosen as comonomers to achieve improved transparency and thermal stability while maintaining the refractive index. The sulfur, ‐C = N‐, and imide contents in the copolymers were varied by adjusting the monomer structures and their compositions, and their effects on the refractive index, Abbe number, and optical and thermal properties were investigated. The MeTVS monomer in poly(MeSTVS) and poly(MeSTVS‐co‐NVPI) contained three sulfur atoms and two ‐C = N‐ units; consequently, these polymers exhibited excellent refractive indices in the 1.7139–1.6567 range at 589 nm, Abbe numbers between 19.1–29.1, good transparency (>90% at 400 nm), and tunable thermal properties (Tg = 49–138 °C, Td10 = 244–268 °C). Optically transparent poly(1,3,4‐TVS‐co‐NVPI) films (> 95% at 400 nm) with improved thermal stability (Tg = 89–175 °C, Td10 = 251–301 °C) were obtained, while maintaining a relatively high refractive index (1.6662–1.6752).This article is protected by copyright. All rights reserved

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Facile synthesis of high refractive index thiophene‐containing polystyrenes

Cited by 16 publications

References 65 publications

Highly Transparent Benzothiazole-Based Block and Random Copolymers with High Refractive Indices by RAFT Polymerization

Highly Transparent Benzothiazole-Based Block and Random Copolymers with High Refractive Indices by RAFT Polymerization

Intrinsic High Refractive Index Siloxane–Sulfide Polymer Networks Having High Thermostability and Transmittance via Thiol–Ene Cross-Linking Reaction

High Refractive Index Copolymers from Aromatic Heterocycle‐Based Vinyl Sulfides and Phthalimide/Maleimide Derivatives

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