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RESEARCH FRONT
Contents Vol 65(7)

Novel Semiconducting Biomaterials Derived from a Proline Ester and Tetracyanoquinodimethane Identified by Handpicked Selection of Individual Crystals*

Lisandra L. Martin A D , Jinzhen Lu A , Ayman Nafady A , Thanh Hai Le A , Amal I. Siriwardana A B , Xiaohu Qu A , Daouda A. K. Traore C , Matthew Wilce C and Alan M. Bond A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

B ARC Special Research Centre for Green Chemistry, Monash University, Clayton, Vic. 3800, Australia.

C Department of Biochemistry and Molecular Biology, Monash University, Wellington Road, Clayton, Vic. 3800, Australia.

D Corresponding author. Email: lisa.martin@monash.edu

Australian Journal of Chemistry 65(7) 935-941 https://doi.org/10.1071/CH12183
Submitted: 5 April 2012  Accepted: 1 May 2012   Published: 2 August 2012

Abstract

Complex mixtures of cation : anion stoichometries often result from the syntheses of tetracyanoquinodimethane (TCNQ) salts, and often these cannot be easily separated. In this study, the reaction of N,N-dimethyl-d-proline-methylester (Pro(CH3)3+) with LiTCNQ resulted in a mixture of crystals. Hand selection and characterisation of each crystal type by X-ray, infrared, Raman and electrochemistry has provided two stoichometries, 1 : 1 [Pro(CH3)3TCNQ] and 2 : 3 ([(Pro(CH3)3)2(TCNQ)3]). A detailed comparison of these structures is provided. The electrochemical method provides an exceptionally sensitive method of distinguishing differences in stoichiometry. The room temperature conductivity of the mixture is 3.1 × 10–2 S cm–1, which lies in the semiconducting range.


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