Issue 40, 2020

Metathesis polymerization of monomers containing two diphenylacetylene units: synthesis and properties of poly(diphenylacetylene)s bearing diphenylacetylene units on the side chain

Abstract

The metathesis polymerization of monomers containing two diphenylacetylene units [Me3SiC6H4C[triple bond, length as m-dash]CC6H4C[triple bond, length as m-dash]CR; R = o-SiMe3C6H4 (1a), o,o-(SiMe3)2C6H3 (1b), o,o,p-(SiMe3)3C6H2 (1c), and o-CF3C6H4 (1d)] was performed using TaCl5/n-Bu4Sn. The polymerization of 1a–c containing SiMe3 group at the ortho position of a benzene ring afforded solvent-soluble products (2a–c) without crosslinking since the reaction of one acetylene was suppressed by steric hindrance. In contrast, the polymerization of 1d containing CF3 group afforded a solvent-insoluble product (2d). Polymers 2a–c exhibited similar thermal stability with a high decomposition temperature (T0 = 380 °C). Upon excitation with 400 nm light, 2a–c exhibited emissions (530 nm) at a longer wavelength than that of poly(diphenylacetylene) without a phenylacetylene on the side group. In addition, 2b and 2c exhibited intense fluorescence. The oxygen permeability coefficients of 2a–c were 54.3, 268, and 375 barrer, respectively. Gas diffusivity and solubility increased with increasing number of SiMe3 groups in the repeating unit.

Graphical abstract: Metathesis polymerization of monomers containing two diphenylacetylene units: synthesis and properties of poly(diphenylacetylene)s bearing diphenylacetylene units on the side chain

Supplementary files

Article information

Article type
Paper
Submitted
20 Aug 2020
Accepted
17 Sep 2020
First published
24 Sep 2020

Polym. Chem., 2020,11, 6471-6478

Metathesis polymerization of monomers containing two diphenylacetylene units: synthesis and properties of poly(diphenylacetylene)s bearing diphenylacetylene units on the side chain

T. Sakaguchi, H. Shimada and T. Hashimoto, Polym. Chem., 2020, 11, 6471 DOI: 10.1039/D0PY01182G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements