In this work, we wish to report the first member of a new family of organic semi-conductors constructed on a meta dihydroindacenodithiophene core, that is 2,2'-(2,8-dihexyl-4,6-dihydro-s-indaceno [1,2-b:7,6-b']dithiophene-4,6-diylidene)dimalononitrile (called meta-IDT(=C(CN) 2 ) 2 ). The properties of this molecule have been studied in detail through a structure properties relationship study with its regioisomer, that is 2,2'-(2,7-dihexyl-4,9-dihydro-s-indaceno [1,2-b:5,6-b']dithiophene-4,9-diylidene)dimalononitrile (para-IDT(=C(CN) 2 ) 2 ) (see isomers structures in blue in Chart 2). The influence of the bridge functionalization has also been investigated by comparison with their diketone analogues meta-IDT(=O) 2 and para-IDT(=O) 2 . This study sheds light on the impact of regioisomerism on the electronic properties at the molecular level (electrochemistry, absorption spectroscopy, molecular modelling) and also on the supramolecular arrangement (SWAXS), and finally on the OFET performances and stabilities. The significant effect of self-assembled monolayers of 4-(dimethylamino) benzenethiol (DABT) grafted on the gold drain and source electrodes or of the use of flexible substrate (polyethylene naphtalate: PEN) instead of glass on the OFET performances and stabilities are also reported. In the light of these results (maximum mobility reaching 7.1×10 -2 cm² V -1 cm -1 , high Id on /Id off of 2.3×10 7 and