α-substituent effect on o -vinylbenzaldehyde cyclopolymerization

Bora Inci; Pin Nan Cheng; Kyle Beljanski; Jeffrey S. Moore

doi:10.1021/mz4004908

α-substituent effect on o -vinylbenzaldehyde cyclopolymerization

Bora Inci, Pin Nan Cheng, Kyle Beljanski, Jeffrey S. Moore

Research output: Contribution to journal › Article › peer-review

Abstract

The cationic cyclopolymerization of o-vinylbenzaldehydes initiated by boron trifluoride is described. Unlike the incomplete conversion of o-vinylbenzaldehyde (1) at 0 C, α-methyl-substituted monomers (2) and (3) undergo cyclopolymerizations with complete conversions at -78 C. On the other hand, α-phenyl-substituted monomer (4) generated indenyl alcohol (7) when subjected to cationic polymerization conditions. The proposed mechanism for o-(α-methyl)vinylbenzaldehyde polymerization explains the importance of reaction temperature for polymer formation. Resulting amorphous poly(o-(α-methyl)vinylbenzaldehyde (10) exhibited good thermal stability (T_onset = 340 C) with a T_g of 153 C. Polymer (10) is a brittle and glassy plastic with a storage modulus (E′) of 3 × 10⁸ Pa and elongation at break of ∼3%.

Original language	English (US)
Pages (from-to)	935-938
Number of pages	4
Journal	ACS Macro Letters
Volume	2
Issue number	10
DOIs	https://doi.org/10.1021/mz4004908
State	Published - Oct 28 2013

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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10.1021/mz4004908

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abstract = "The cationic cyclopolymerization of o-vinylbenzaldehydes initiated by boron trifluoride is described. Unlike the incomplete conversion of o-vinylbenzaldehyde (1) at 0 C, α-methyl-substituted monomers (2) and (3) undergo cyclopolymerizations with complete conversions at -78 C. On the other hand, α-phenyl-substituted monomer (4) generated indenyl alcohol (7) when subjected to cationic polymerization conditions. The proposed mechanism for o-(α-methyl)vinylbenzaldehyde polymerization explains the importance of reaction temperature for polymer formation. Resulting amorphous poly(o-(α-methyl)vinylbenzaldehyde (10) exhibited good thermal stability (Tonset = 340 C) with a Tg of 153 C. Polymer (10) is a brittle and glassy plastic with a storage modulus (E′) of 3 × 108 Pa and elongation at break of ∼3%.",

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T1 - α-substituent effect on o -vinylbenzaldehyde cyclopolymerization

AU - Inci, Bora

AU - Cheng, Pin Nan

AU - Beljanski, Kyle

AU - Moore, Jeffrey S.

PY - 2013/10/28

Y1 - 2013/10/28

N2 - The cationic cyclopolymerization of o-vinylbenzaldehydes initiated by boron trifluoride is described. Unlike the incomplete conversion of o-vinylbenzaldehyde (1) at 0 C, α-methyl-substituted monomers (2) and (3) undergo cyclopolymerizations with complete conversions at -78 C. On the other hand, α-phenyl-substituted monomer (4) generated indenyl alcohol (7) when subjected to cationic polymerization conditions. The proposed mechanism for o-(α-methyl)vinylbenzaldehyde polymerization explains the importance of reaction temperature for polymer formation. Resulting amorphous poly(o-(α-methyl)vinylbenzaldehyde (10) exhibited good thermal stability (Tonset = 340 C) with a Tg of 153 C. Polymer (10) is a brittle and glassy plastic with a storage modulus (E′) of 3 × 108 Pa and elongation at break of ∼3%.

AB - The cationic cyclopolymerization of o-vinylbenzaldehydes initiated by boron trifluoride is described. Unlike the incomplete conversion of o-vinylbenzaldehyde (1) at 0 C, α-methyl-substituted monomers (2) and (3) undergo cyclopolymerizations with complete conversions at -78 C. On the other hand, α-phenyl-substituted monomer (4) generated indenyl alcohol (7) when subjected to cationic polymerization conditions. The proposed mechanism for o-(α-methyl)vinylbenzaldehyde polymerization explains the importance of reaction temperature for polymer formation. Resulting amorphous poly(o-(α-methyl)vinylbenzaldehyde (10) exhibited good thermal stability (Tonset = 340 C) with a Tg of 153 C. Polymer (10) is a brittle and glassy plastic with a storage modulus (E′) of 3 × 108 Pa and elongation at break of ∼3%.

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α-substituent effect on o -vinylbenzaldehyde cyclopolymerization

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