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Issue 2, 2015
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Dibenzo[a,e]pentalene-embedded dicyanomethylene-substituted thienoquinoidals for n-channel organic semiconductors: synthesis, properties, and device characteristics

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Abstract

Dibenzo[a,e]pentalene-embedded thienoquinoidals with dicyanomethylene termini were synthesized as new π-extended thienoquinoidals for n-type organic semiconductors. Single crystal X-ray analysis demonstrated that the target molecule has an all trans-polyene structure with reasonable bond-length alternation in the thienoquinoidal strand, indicative of effective extension of the π-conjugation system. Thanks to their π-extended structures, not just the low-lying LUMO energy levels (−4.2 to −4.3 eV) but also relatively high HOMO energy levels (∼−5.6 eV) were characterized by means of cyclic voltammetry. Interestingly, depending on the position of the solubilizing long alkyl groups, they formed H- or J-aggregate-like structures in the thin-film state testified by the thin film absorption spectra. These distinct intermolecular interactions in the thin film state could cause different behaviours in thin-film field-effect transistors; for the former ambipolar characteristics were observed, whereas only n-type response was detected for the latter.

Graphical abstract: Dibenzo[a,e]pentalene-embedded dicyanomethylene-substituted thienoquinoidals for n-channel organic semiconductors: synthesis, properties, and device characteristics

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Publication details

The article was received on 25 Sep 2014, accepted on 29 Oct 2014 and first published on 03 Nov 2014


Article type: Paper
DOI: 10.1039/C4TC02164A
Citation: J. Mater. Chem. C, 2015,3, 283-290
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    Dibenzo[a,e]pentalene-embedded dicyanomethylene-substituted thienoquinoidals for n-channel organic semiconductors: synthesis, properties, and device characteristics

    M. Nakano, I. Osaka and K. Takimiya, J. Mater. Chem. C, 2015, 3, 283
    DOI: 10.1039/C4TC02164A

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