Synthesis and Characterization of Benzothieno[3,2-<italic style="font-style: italic">b</italic>]benzothiophene-based High-refractive-index Polyacrylates and Polycarbonates

Guo-Rong Chen; Xiao-Zhong Yang; Jing-Song You; Jing-Bo Lan

doi:10.1007/s10118-026-3864-6

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Synthesis and Characterization of Benzothieno[3,2-b]benzothiophene-based High-refractive-index Polyacrylates and Polycarbonates

RESEARCH ARTICLE | Updated：2026-11-05

- Synthesis and Characterization of Benzothieno[3,2-b]benzothiophene-based High-refractive-index Polyacrylates and Polycarbonates
- Chinese Journal of Polymer Science Vol. 44, Pages: 1-7(2026)
- Affiliations：
  
  Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
- Author bio：
  
  jingbolan@scu.edu.cn
- Funds：
- DOI：10.1007/s10118-026-3864-6
  CLC：
- Received：27 July 2026，
  
  Accepted：28 August 2026，
  
  Online First：05 November 2026，
  
  Published：2026-10
- Accepted：
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Chen, G. R.; Yang, X. Z.; You, J. S.; Lan, J. B. Synthesis and characterization of benzothieno[3,2-b]benzothiophene-based high-refractive-index polyacrylates and polycarbonates. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-026-3864-6

Guo-Rong Chen, Xiao-Zhong Yang, Jing-Song You, et al. Synthesis and Characterization of Benzothieno[3,2-b]benzothiophene-based High-refractive-index Polyacrylates and Polycarbonates[J/OL]. Chinese Journal of Polymer Science, 2026, 441-7. DOI: 10.1007/s10118-026-3864-6.
Chen, G. R.; Yang, X. Z.; You, J. S.; Lan, J. B. Synthesis and characterization of benzothieno[3,2-b]benzothiophene-based high-refractive-index polyacrylates and polycarbonates. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-026-3864-6 DOI：

Guo-Rong Chen, Xiao-Zhong Yang, Jing-Song You, et al. Synthesis and Characterization of Benzothieno[3,2-b]benzothiophene-based High-refractive-index Polyacrylates and Polycarbonates[J/OL]. Chinese Journal of Polymer Science, 2026, 441-7. DOI: 10.1007/s10118-026-3864-6. DOI：

摘要

Abstract

Driven by the demand for miniaturized monolithic optoelectronic integration

high-refractive-index polymers (HRIPs) with superior thermal and optical characteristics remain a central research priority. Despite its compact

sulfur-rich fused-ring framework

benzothieno[3

]

benzothiophene (BTBT) has yet to be exploited as a building block for HRIPs. This study integrates the BTBT unit into two distinct polymer architectures. In the first approach

a pendant-BTBT acrylate monomer (

BPN3A

) was copolymerized with methyl acrylate

via

free-radical polymerization

yielding a series of polyacrylates (

Poly 1–Poly 5

). Their refractive indices (

) increased linearly from 1.519 to 1.707 as

BPN3A

content rose

with the homopolymer

value extrapolated to 1.741.

Poly 1–Poly 5

displayed high thermal stability with decomposition temperatures (

) ranging from 325 °C to 359 °C and glass transition temperatures (

) up to 93 °C.

Poly 1

retained an Abbe number of 11.6 while maintaining transmittance exceeding 90% at 470 nm. In the second approach

a BTBT-based diol monomer (

9-BE

) was incorporated into polycarbonate backbone through melt polycondensation

affording

Poly 7

which exhibited an

of 1.665 and transmittance approaching 80% at 400 nm with an Abbe number of 13.9.

Poly 7

maint

ained moderate thermal stability with a

of 306 °C and a

of 89 °C. Incorporating the sulfur-rich

highly polarizable BTBT unit as either a pendant substituent or a backbone component therefore provides a viable molecular design strategy for HRIPs.

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references

Higashihara, T.; Ueda, M. Recent progress in high refractive index polymers. Macromolecules 2015 , 48 , 1915−1929..

Ma, L.; Ma, M. J.; Nie, J.; Zhu, X. Q. Advances in high-refractive-index monomers containing unsaturated groups. Macromol. Rapid Commun. 2025 , 46 , 2500037..

Pillay, R.; Hansraj, R.; Rampersad, N. Historical development, applications and advances in materials used in spectacle lenses and contact lenses. Clin. Optom. 2020 , 12 , 157−167..

Wei, Q.; Pötzsch, R.; Liu, X.; Komber, H.; Kiriy, A.; Voit, B.; Will, P. A.; Lenk, S.; Reineke, S. Hyperbranched polymers with high transparency and inherent high refractive index for application in organic light-emitting diodes. Adv. Funct. Mater. 2016 , 26 , 2545−2553..

Liu, J. G.; Nakamura, Y.; Ogura, T.; Shibasak i, Y.; Ando, S.; Ueda, M. Optically transparent sulfur-containing polyimide–TiO 2 nanocomposite films with high refractive index and negative pattern formation from poly(amic acid)–TiO 2 nanocomposite film. Chem. Mater. 2008 , 20 , 273−281..

Ma, H.; Jen, A. K.; Dalton, L. R. Polymer-based optical waveguides: materials, processing, and devices. Adv. Mater. 2002 , 14 , 1339−1365..

Zhang, J.; Bai, T.; Liu, W.; Li, M.; Zang, Q.; Ye, C.; Sun, J. Z.; Shi, Y.; Ling, J.; Qin, A.; Tang, B. Z. All-organic polymeric materials with high refractive index and excellent transparency. Nat. Commun. 2023 , 14 , 3524..

Tang, Y.; Pina-Hernandez, C.; Niu, Q.; Nie, J.; Cabrini, S. A novel high-refractive index episulfide-thiol polymer for nanoimprinting optical elements. J. Mater. Chem. C 2018 , 6 , 8823−8831..

[Kleine, T. S.; Glass, R. S.; Lichtenberger, D. L.; MacKay, M. E.; Char, K.; Norwood, R. A.; Pyun, J. 100th anniversary of macromolecular science viewpoint: high refractive index polymers from elemental sulfur for infrared thermal imaging and optics. ACS Macro Lett . 2020 , 9 , 245−259..

MacDonald, E. K.; Shaver, M. P. Intrinsic high refractive index polymers. Polym. Int. 2015 , 64 , 6−14..

Mazumder, K.; Voit, B.; Banerjee, S. Recent progress in sulfur-containing high refractive index polymers for optical applications. ACS Omega 2024 , 9 , 6253−6279..

[Träger, F. in Springer handbook of lasers and optics . Springer, Berlin, Heidelberg, 2012, p. 459..

Molineux, J.; Kim, K. J.; Gul, A.; Durfee, S. W.; Norwood, R. A.; Pyun, J. Plastic optical glass as a critical material for optics and photonics. Prog. Polym. Sci. 2026 , 174 , 102088..

Bao, J.; Kang, K. S.; Molineux, J.; Bischoff, D. J.; MacKay, M. E.; Pyun, J.; Njardarson, J. T. Dithiophosphoric acids for polymer functionalization. Angew. Chem. Int. Ed. 2024 , 63 , e202315963..

Fang, L.; Sun, J.; Chen, X.; Tao, Y.; Zhou, J.; Wang, C.; Fang, Q. Phosphorus- and sulfur-containing high-refractive-index polymers with high T g and transparency derived from a bio-based aldehyde. Macromolecules 2020 , 53 , 125−131..

Li, W.; Ding, Y.; Gao, H.; Pan, L.; Li, Y. Design and synthesis of colorless cyclic olefin polymers with high refractive index, transparency, and thermal stability. Macromolecules 2025 , 58 , 9459−9468..

Tokushita, Y.; Furuya, S.; Nobe, S.; Nakabayashi, K.; Samitsu, S.; Mori, H. Preparation of highly transparent poly(meth)acrylates with enhanced refractive indices by radical (co)polymerization of seleno (meth)acrylates. Polymer 2021 , 237 , 124346..

Watanabe, S.; Oyaizu, K. Designing strategy for high refractive index polymers: from the molecular level to bulk structure control. Bull. Chem. Soc. Jpn. 2023 , 96 , 1108−1128..

Feng, L. K.; Zhang, A. W.; Huang, G. H.; Zhu, C. Z.; Wang, M. L.; Xu, J. Molecular designs of sulfur-containing high refractive index and Abbe number polymers using density functional theory. Chinese J. Polym. Sci. 2025 , 43 , 1253−1268..

Lorenz, L. Ueber die refractionsconstante. Ann. Der Phys. 1880 , 247 , 70−103..

Olikagu, C.; Khoshsorour, S.; Dulam, S. D.; Yu, H. S.; Graham, N. A.; Kim, K. J.; Jeong, B.; Hedrick, J. L.; Bunnag-Stoner, A.; Cheng, K.; Batchelor, B. L.; Cho, W.; Bin Park, S.; Wie, J. J.; Kim, Y. J.; Bog, M. G.; Krishnan, N. B.; Yang, Y. Y.; Njardarson, J. T.; Norwood, R. A.; Pyun, J. Photopolymer resins from sulfenyl chloride commodity chemicals for plastic optics, photopatterning and 3D-printing. Adv. Mater. 2025 , 37 , 2418149..

Rice, J. E.; Handy, N. C. The calculation of frequency-dependent polarizabilities as pseudo-energy derivatives. J. Chem. Phys. 1991 , 94 , 4959−4971..

Dou, Z.; Zhang, H.; Li, J.; Sun, J.; Fang, Q. Biobased sulfur- and phosphate-containing high-refractive-index polymers: substituent effects on optical properties of polymers. Biomacromolecules 2024 , 25 , 8038−8045..

Nishi, M.; Komeda, M.; Aoyagi, N.; Yoshida, Y.; Endo, T. Synthesis and fundamental properties of methacrylate polymer containing five-membered cyclic trithiocarbonate group. J. Polym. Sci. 2020 , 58 , 2126−2133..

Qiu, Y.; Li, J.; Li, T.; Ma, X.; Jiang, X. Photo-curing vis-IR hybrid Fresnel lenses with high refractive index. Macromol. Chem. Phys. 2021 , 222 , 2100311..

Sato, Y.; Sobu, S.; Nakabayashi, K.; Samitsu, S.; Mori, H. Highly transparent benzothiazole-based block and random copolymers with high refractive indices by RAFT polymerization. ACS Appl. Polym. Mater. 2020 , 2 , 3205−3214..

Su, Y.; Filho, E. B. D. S.; Peek, N.; Chen, B.; Stiegman, A. E. High refractive index polymers ( n > 1.7), based on thiol–ene cross-linking of polarizable P═S and P═Se organic/inorganic monomers. Macromolecules 2019 , 52 , 9012−9022..

Wuliu, Y.; Huang, G.; Tan, J.; Dong, W.; Huang, H.; Mu, K.; Feng, L.; Wang, M. G.; Tian, L.; Zhu, C.; Xu, J. High refractive index and high abbe number polymer based on norbornadiene. Macromolecules 2023 , 56 , 9881−9887..

Zhou, Y.; Zhu, Z.; Zhang, K.; Yang, B. Molecular structure and properties of sulfur-containing high refractive index polymer optical materials. Macromol. Rapid Commun. 2023 , 44 , 2300411..

Zhu, H.; Chen, M.; Zhou, S.; Wu, L. Synthesis of high refractive index and shape controllable colloidal polymer microspheres for super-resolution imaging. Macromolecules 2017 , 50 , 660−665..

Watanabe, K.; Enomoto, K.; Nagasawa, T.; Matsuda, M.; Katagiri, H.; Kawaguchi, S.; Ando, S.; Ueda, M.; Higashihara, T. Synthesis of novel alicyclic poly(thioether sulfone) with high refractive index and high Abbe’s number using 1,4-dithiin 1,1-dioxide. Macromolecules 2025 , 58 , 4138−4146..

Zhao, J. Z.; Yue, T. J.; Ren, B. H.; Ma, Y. X.; Lu, X. B.; Ren, W. M. Chemically recyclable poly(tetrathioorthocarbonate)s: combining high refractive index and Abbe number. J. Am. Chem. Soc. 2025 , 147 , 19762−19769..

Hifumi, R.; Takai, A.; Tomita, I. Synthesis of aromatic poly(thioether)s with phosphine sulfide groups for high-refractive-index materials. ACS Omega 2026 , 11 , 22220−22227..

Chen, H.; Zhang, W.; Li, M.; He, G.; Guo, X. Interface engineering in organic fi eld-effect transistors: principles, applications, and perspectives. Chem. Rev. 2020 , 120 , 2879−2949..

Minemawari, H.; Yamada, T.; Matsui, H.; Tsutsumi, J.; Haas, S.; Chiba, R.; Kumai, R.; Hasegawa, T. Inkjet printing of single-crystal films. Nature 2011 , 475 , 364−367..

Takimiya, K.; Osaka, I.; Mori, T.; Nakano, M. Organic semiconductors based on [1 ] benzothieno[3,2-b ] [1 ] benzothiophene substructure. Acc. Chem. Res. 2014 , 47 , 1493−1502..

Wu, X.; Zhu, X.; Sun, L.; Zhang, S.; Ren, Y.; Wang, Z.; Zhang, X.; Yang, F.; Zhang, H. L.; Hu, W. Navigating the transitional window for organic semiconductor single crystals towards practical integration: from materials, crystallization, and technologies to real-world applications. Chem. Soc. Rev. 2025 , 54 , 1699−1732..

Cao, Y.; Feng, J.; Nallapaneni, A.; Arakawa, Y.; Zhao, K.; Zhang, H.; Mehl, G. H.; Zhu, C.; Liu, F. Deciphering helix assembly in the heliconical nematic phase via tender resonant X-ray scattering. J. Mater. Chem. C 2021 , 9 , 10020−10028..

Maheswara, M.; Oh, S. H.; Ju, J. J.; Park, S. K.; Park, S.; Do, J. Y. High refractive index of transparent acrylate polymers functionalized with alkyl sulfur groups. Polym. J. 2010 , 42 , 249−255..

Tapaswi, P. K.; Choi, M. C.; Jeong, K. M.; Ando, S.; Ha, C. S. Transparent aromatic polyimides derived from thiophenyl-substituted benzidines with high refractive index and small birefringence. Macromolecules 2015 , 48 , 3462−3474..

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Synthesis and Characterization of Benzothieno[3,2-b]benzothiophene-based High-refractive-index Polyacrylates and Polycarbonates

DOI：10.1007/s10118-026-3864-6

摘要

Abstract

关键词

Keywords

references