Synthesis, crystal structure, tropicity and charge transport properties of diindenothienothiophene derivatives

Tanguy Jousselin-Oba (1) , Masashi Mamada (2) , Karen Wright (1) , Jérôme Marrot (1) , Chihaya Adachi (2) , Abderrahim Yassar (3) , Michel Frigoli (1)

1 ILV - Institut Lavoisier de Versailles
2 Kyushu University
3 LPICM - Laboratoire de physique des interfaces et des couches minces [Palaiseau]

A set of π-conjugated diindenothienothiophene derivatives (DITTs) which formally possess an extended as-indacene core with 16 π-electrons has been synthesised and their closed-shell configuration has been confirmed by X-ray structure analysis. Bond lengths analysis provides insight into the peculiar bond lengths observed for diindenoacene diradicaloids. The annellation mode at the outer rings has a great impact on the tropicity, optoelectrochemical properties and molecular packing. The featured molecules exhibit low energy band gap with values up to 1.30 eV and have high electron affinities with LUMO energies up to 3.86 eV. Their optical properties are similar to those of benzo-fused indeno[2,1-c]fluorene (BIFs) counterparts possessing formally the as-indacene core. Analysis of the molecule tropicity using NICS and ACID plot shows that the central rings of DITTs are weakly antiaromatic and should be regarded as quinoidal molecules bridged by two sulphur atoms. Three out of four molecules show ambipolar behavior in OFETs with moderate mobilities

Domaines: Chimie organique; Cristallographie

Tanguy Jousselin-Oba, Masashi Mamada, Karen Wright, Jérôme Marrot, Chihaya Adachi, et al.. Synthesis, crystal structure, tropicity and charge transport properties of diindenothienothiophene derivatives. Journal of Materials Chemistry C, In press, ⟨10.1039/D2TC01324J⟩. ⟨hal-03663987⟩