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Issue 39, 2017
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Synthesis and investigation on processing-depending polarized fluorescence emission in thin-films of 2,2′-([2,2′-bithiophene]-5,5′-diyl)bis(5-octyl-4-phenyl-4H-thieno[2,3-c]pyrrol-6(5H)-one)

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Abstract

Thienopyrrole-dione (TI) end capped materials have recently emerged as polymorphic molecular semiconductors suitable as active layers of ambipolar light emitting transistors, photovoltaic cells and time temperature integrator devices. Here, we report the synthesis of a new derivative, namely 2,2′-([2,2′-bithiophene]-5,5′-diyl)bis(5-octyl-4-phenyl-4H-thieno[2,3-c]pyrrol-6(5H)-one) (R-NT4N), having monoreduced TI moiety (R-TI) end groups. Ring opening of the TI moiety by Grignard reagent addition followed by one-pot reduction/ring closure by triethylsilane afforded the R-TI precursor that was then exploited for the preparation of the target R-NT4N compound. Investigation of the fluorescence properties of thin films, as a function of the processing conditions, showed that different from all the other TI derivatives so far reported, R-NT4N exhibits linearly polarized fluorescent microstructures. Combined micro-Raman and confocal laser-scanning fluorescence microscopies on lithographically controlled wetting (LCW) patterned R-NT4N films allowed us to correlate the emission polarization directions with the microcrystal structures.

Graphical abstract: Synthesis and investigation on processing-depending polarized fluorescence emission in thin-films of 2,2′-([2,2′-bithiophene]-5,5′-diyl)bis(5-octyl-4-phenyl-4H-thieno[2,3-c]pyrrol-6(5H)-one)

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Publication details

The article was received on 28 Aug 2017, accepted on 12 Sep 2017 and first published on 13 Sep 2017


Article type: Paper
DOI: 10.1039/C7TC03930A
Citation: J. Mater. Chem. C, 2017,5, 10320-10331
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    Synthesis and investigation on processing-depending polarized fluorescence emission in thin-films of 2,2′-([2,2′-bithiophene]-5,5′-diyl)bis(5-octyl-4-phenyl-4H-thieno[2,3-c]pyrrol-6(5H)-one)

    L. Favaretto, M. Zambianchi, S. G. Lopez, A. Mazzanti, C. Zanardi, R. Seeber, D. Gentili, F. Valle, E. Benvenuti, M. Muccini, G. Ruani, F. Mercuri, S. Milita, F. Liscio, M. Cavallini, S. Toffanin and M. Melucci, J. Mater. Chem. C, 2017, 5, 10320
    DOI: 10.1039/C7TC03930A

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