Precise synthesis of high T-g adamantane-containing polystyrene derivatives via anionic polymerization
- Authors
- Kang, Beom-Goo
- Issue Date
- May-2023
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- POLYMER CHEMISTRY, v.14, no.19, pp.2374 - 2382
- Journal Title
- POLYMER CHEMISTRY
- Volume
- 14
- Number
- 19
- Start Page
- 2374
- End Page
- 2382
- URI
- http://scholarworks.bwise.kr/ssu/handle/2018.sw.ssu/43930
- DOI
- 10.1039/d3py00238a
- ISSN
- 1759-9954
- Abstract
- The precise synthesis of poly(4-(4-(N-adamantylimino)methyl)phenylstyrene) was attempted via anionic polymerization of 4-(4-(N-adamantylimino)methyl)phenylstyrene to examine the substituent effect of polystyrene derivatives on their glass transition temperature (T-g) and the reactivity of 4-(4-(N-adamantylimino)methyl)phenylstyrene. The anionic polymerization of 4-(4-(N-adamantylimino)methyl)phenylstyrene was carried out with diverse initiator systems, such as oligo(alpha-methylstyryl)lithium, oligo(alpha-methylstyryl)dipotassium, and (1,1,4,4-tetraphenylbutanediyl)dipotassium, in tetrahydrofuran at -78 degrees C. It produced well-controlled poly(4-(4-(N-adamantylimino)methyl)phenylstyrene) with the expected molecular weight and narrow molecular weight distribution. Sequential block copolymerization with 2-vinylpyridine as the first monomer resulted in the successful synthesis of well-defined poly(2-vinylpyridine)-block-poly(4-(4-(N-adamantylimino)methyl)phenylstyrene), indicating high monomer reactivity of 4-(4-(N-adamantylimino)methyl)phenylstyrene. The postpolymerization modification of poly(4-(4-(N-adamantylimino)methyl)phenylstyrene) and poly(2-vinylpyridine)-block-poly(4-(4-(N-adamantylimino)methyl)phenylstyrene) led to the quantitative preparation of poly(4,4 '-formylphenylstyrene) and poly(2-vinylpyridine)-block-poly(4,4 '-formylphenylstyrene), respectively, with an electrophilic formyl group. Thermogravimetric analysis and differential scanning calorimetry confirmed that poly(4-(4-(N-adamantylimino)methyl)phenylstyrene) prepared in this study had high thermal stability and a high T-g owing to the bulky and rigid adamantyl group. In particular, among the adamantane-containing polystyrene derivatives reported thus far, high molecular weight poly(4-(4-(N-adamantylimino)methyl)phenylstyrene) showed the highest T-g (268 degrees C).
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