The study of a [1]Benzothieno [3,2-b][1]benzothiophene (BTBT) derivative decorated with hexyl chains functionalized with hydroxyl end groups is reported. A rapid and inexpensive functionalization of the BTBT in position 2 and 7 has been developed. This compound is able to self-organize into a lamellar structure through σ-π stacking and van der Waals interactions but also through hydrogen bonding interactions. The hydrogen-bonded network controls the interlamellar region in terms of organization and stability. Liquid-crystal phase and structural changes observed by DSC have been characterized using an original approach combining FTIR and powder XRD measurements as a function of temperature. Thermally evaporated diol based OFETs exhibited good mobilities up to 0.17 cm².V-1.s-1 measured under inert atmosphere but also in ambient air. The diol derivative is considered as a very promising platform for the design of new functionalized BTBT.

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Determination of kryptoracemic compound frequency in the Cambridge Structural Database using CCDC Python API script.