Issue 1, 2012

Preparation and properties of two-legged ladder polymers based on polydiacetylenes

Abstract

A novel diacetylene derivative, N,N′-bis[5-(3-tolylaminocarbonyloxy)-1,3-pentadiynyl]-N,N′-diphenyl-1,4-phenylenediamine (1), was prepared, where two diacetylene groups were connected by a 1,4-phenylenediamine moiety. The molecules stacked one-dimensionally and showed solid-state-polymerization reactivity above 80 °C. The decay of the monomers at 100 °C proceeded gradually without a marked induction period and was fully completed after 400 h. The obtained polymer was a crystalline solid judged by powder X-ray diffraction (PXRD) patterns and SEM imaging. The conjugated π-system of the obtained polymer was classified as a two-legged conjugated ladder. The polymer showed a broad absorption from the visible to the near IR region, indicating a decrease in the optical band gap of ca. 1.0 eV, because of the expansion of the π-conjugated system from a one-dimensional system to a ladder. The ladder polymer showed high conductivity after I2 doping from σ293K = 5 × 10−12 S cm−1 to 1.2 × 10−5 S cm−1. The conductivity depended heavily on the pressure of iodine and reached σ373K = 2.3 × 10−1 S cm−1. The activation energy of the ladder polymer was also estimated as 360 meV.

Graphical abstract: Preparation and properties of two-legged ladder polymers based on polydiacetylenes

Supplementary files

Article information

Article type
Paper
Submitted
11 Aug 2011
Accepted
11 Sep 2011
First published
31 Oct 2011

J. Mater. Chem., 2012,22, 115-122

Preparation and properties of two-legged ladder polymers based on polydiacetylenes

H. Tabata, H. Tokoyama, H. Yamakado and T. Okuno, J. Mater. Chem., 2012, 22, 115 DOI: 10.1039/C1JM13896K

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.

Spotlight

Advertisements