Issue 16, 2013
From the journal:

Polymer Chemistry

Photo-induced denitrogenation of triazoline moieties for efficient photo-assisted poling of electro-optic polymers

Ming Li,ab   Zhian Jin,a   Nathan Cernetic,a   Jingdong Luo,*a   Zhanchen Cui*b  and  Alex K.-Y. Jen*a  

* Corresponding authors

a Department of Materials Science and Engineering, University of Washington, Seattle, Washington 98195, USA
E-mail: ajen@uw.edu, jdluo@uw.edu
Fax: +1 206 543 3100
Tel: +1 206 543 2626

b State Key Lab of Supramolecular Structure & Materials, College of Chemistry, Jilin University, 2699# Qianjin Road, Changchun 130012, PR China
E-mail: cuizc@jlu.edu.cn
Fax: +86 431 85193423
Tel: +86 431 85168217

Abstract

Efficient room temperature poling of a guest–host electro-optic (EO) polymer is achieved by photo-induced denitrogenation of triazoline moieties. The host polymer (P1) with Δ2-1,2,3-triazoline groups on the backbone is synthesized by 1,3-dipolar cycloaddition polymerization between a bis-N-phenylmaleimide and an aromatic bis-azide. The guest chromophore (C1) is a push–pull compound with a strong dialkylaminophenyl donor and a CF3–TCF acceptor. By irradiating the thin films of P1 with a compact UV lamp at 365 nm, the angular and asymmetric 1,2,3-triazoline structures can be readily converted into a more straight and symmetrical aziridine structure by losing nitrogen. This photo-induced denitrogenation provides the clean conversion to form an aziridine-based polymer P2. This high efficiency conversion process is insensitive to the light-absorbing nonlinear optical chromophores, and the reaction rate can be controlled by the irradiation power and the thin film UV absorbance. Upon the photo-induced denitrogenation, considerable structural change of the polymer backbone provides sufficient rotational freedom to the chromophores for the poling of EO polymers. This has been verified by the demonstration of high field poling (up to 250 V μm−1) and large EO activity at RT for thin films containing 20–25 wt% of chromophore C1 in P1, which can be efficiently activated by photochemical denitrogenation of triazoline moieties by irradiating with low-power UV light.

Graphical abstract: Photo-induced denitrogenation of triazoline moieties for efficient photo-assisted poling of electro-optic polymers

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Article information

DOI
https://doi.org/10.1039/C3PY00480E
Article type
Paper
Submitted
15 Apr 2013
Accepted
29 May 2013
First published
29 May 2013

Polym. Chem., 2013,4, 4434-4441

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Photo-induced denitrogenation of triazoline moieties for efficient photo-assisted poling of electro-optic polymers

M. Li, Z. Jin, N. Cernetic, J. Luo, Z. Cui and A. K.-Y. Jen, Polym. Chem., 2013, 4, 4434 DOI: 10.1039/C3PY00480E

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