Oligo(p-phenylene vinylene)s as a “New” Class of Piezochromic Fluorophores

Authors

  • J. Kunzelman,

    1. Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Rd, Cleveland, OH 44106-7202 (USA)
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  • M. Kinami,

    1. Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Rd, Cleveland, OH 44106-7202 (USA)
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  • B. R. Crenshaw,

    1. Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Rd, Cleveland, OH 44106-7202 (USA)
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  • J. D. Protasiewicz,

    1. Department of Chemistry, Case Western Reserve University, 2100 Adelbert Rd, Cleveland, OH 44106-7202 (USA)
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  • C. Weder

    1. Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Rd, Cleveland, OH 44106-7202 (USA)
    2. Department of Chemistry, Case Western Reserve University, 2100 Adelbert Rd, Cleveland, OH 44106-7202 (USA)
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  • We thank Charles Sing and Shan Tie for technical assistance. This material is based upon work funded by the National Science Foundation (NSF DMI-0428208). We also gratefully acknowledge additional financial support from Kimberly Clark Co. and Toyobo and from the National Science Foundation (CHE 0541766) for funds to purchase the single crystal X-ray diffractometer. Supporting Information is available online from Wiley InterScience or from the authors.

Abstract

original image

Cyano-substituted oligo(p-phenylene vinylene) derivatives can display piezochromic fluorescence. This rare and desirable effect is achieved by balancing π–π and aliphatic interactions in these molecules through the variation of electron density in the central ring and the length of peripheral aliphatic tails. This leads to fluorophores which can adopt different supramolecular structures and as a result can change their solid-state emission characteristics upon compression.

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