Issue 8, 2012
From the journal:

Polymer Chemistry

Colorimetric sensing of cations and anions by clicked polystyrenes bearing side chain donor–acceptor chromophores†

Yongrong Li,a   Minoru Ashizawa,a   Satoshi Uchidaa  and  Tsuyoshi Michinobu*bc  

* Corresponding authors

a Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan

b Global Edge Institute, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550, Japan
E-mail: michinobu.t.aa@m.titech.ac.jp
Fax: +81-3-5734-3774
Tel: +81-3-5734-3774

c Precursory Research for Embryonic Science and Technology (PRESTO), Japan Science and Technology Agency (JST), 4-1-8 Honcho, Kawaguchi-shi, Saitama 332-0012, Japan

Abstract

Donor–acceptor chromophores were introduced into the side chains of a polystyrene derivative through the efficient click postfunctional addition reaction between dialkylaniline-activated alkynes and small acceptors, such as tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ). The resulting polystyrenes were fully characterized by GPC, 1H NMR, IR spectroscopy, and elemental analysis. After the postfunctionalization, the polymers were highly colored due to the formed donor–acceptor chromophores in the side chains and these chromophores showed a colorimetric sensing behavior for some metal ions and anions. Some hard-to-borderline metal ions were always recognized by the dialkylanilino nitrogen atom, resulting in a decrease in the charge-transfer (CT) band intensity of the donor–acceptor chromophores. However, the recognition site of the soft Ag+ ion was the cyano nitrogen atoms due to readily formed multivalent coordination, leading to a bathochromic shift in the CT bands for both TCNE- and TCNQ-adducted polymers. This remarkable dual colorimetric detection of two different types of metal ions was achieved by the elegant design of polymeric chemosensors. On the other hand, it was found that the dicyanoethene moieties of the side chain chromophores serve as a chemodosimeter for some anions. For example, the CN− ion underwent a nucleophilic addition reaction to the electron-deficient ethene moieties, resulting in a dramatic decrease in the CT bands. All types of sensing behavior of both cations and anions were visually recognized. The use of small molecular model compounds enabled the estimation of the kinetic parameters and the product structures.

Graphical abstract: Colorimetric sensing of cations and anions by clicked polystyrenes bearing side chain donor–acceptor chromophores

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2PY20230A
Article type
Paper
Submitted
15 Apr 2012
Accepted
02 May 2012
First published
03 May 2012

Polym. Chem., 2012,3, 1996-2005

Permissions

Request permissions

Colorimetric sensing of cations and anions by clicked polystyrenes bearing side chain donor–acceptor chromophores

Y. Li, M. Ashizawa, S. Uchida and T. Michinobu, Polym. Chem., 2012, 3, 1996 DOI: 10.1039/C2PY20230A

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