Novel semiconducting biomaterials derived from a proline ester and tetracyanoquinodimethane identified by handpicked selection of individual crystals

Lisandra Lorraine Martin, Jinzhen Lu, Ayman Nafady, Thanh Hai Le, Amal Inoka Siriwardana, Xiaohu Qu, Daouda A K Traore, Matthew Charles James Wilce, Alan Maxwell Bond

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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)(3)TCNQ] 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 x 10(-2) S cm(-1), which lies in the semiconducting range.
Original languageEnglish
Pages (from-to)935 - 941
Number of pages7
JournalAustralian Journal of Chemistry
Issue number7
Publication statusPublished - 2012

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