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    Mixed Stack Organic Semiconductors: The Anomalous Case of the BTBT-TCNQF<sub><i>x</i></sub> Series

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    We present a detailed characterization of three mixed stack organic semiconductors, where benzothieno-benzothiophene electron donor is associated with fluorine-substituted TCNQ of increasing electron affinity. BTBT-TCNQ and BTBT-TCNQF<sub>2</sub> are isomorphous, whereas the three-dimensional packing of BTBT-TCNQF<sub>4</sub> is different. Rather surprisingly, we found that the degree of charge transfer is almost constant along the series, at variance with what has been found in analogous cocrystal series in which TCNQF<sub><i>x</i></sub> are involved. We explain this finding in terms of the Madelung energy resulting from interstack packing of the cocrystals, and of the fact that both the HOMO and HOMO–1 of BTBT are involved in the charge transfer mechanism. We also propose that the difference in interstack packing resulting from increasing F substitution is a consequence of electrostatic interactions
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