A bridged syn triphenylene derivative, namely 5,7-dihydroindeno[2,1-b]fluorene, functionalized with dicyanovinylene units (2,1-b)-IF( Q Q QC(CN) 2 ) 2 has been designed, synthesized and characterized. Its optical and electrochemical properties have been carefully studied through a combined experimental and theoretical approach and compared to those of three other structurally related dihydro[2,1-b]indenofluorene derivatives bearing methylenes,which possesses a very low LUMO level, ca. À3.81 eV, has been successfully used as an active layer in n-channel OFETs using an epoxy based photoresist SU-8 as the gate insulator. (2,1-b)-IF(Q Q QC(CN) 2 ) 2 based n-channel OFETs show promising properties such as a low threshold voltage functioning of 7.2 V (low gate-source and drain-source voltages), a high ratio between the on and the off currents (6.3 Â 10 5 ), interesting subthreshold swing (SS = 2.16) and electron mobility (410 À3 cm 2 V À1 s À1 ) and excellent stability under electrical stress. This electrical stability has allowed the incorporation of (2,1-b)-IF(Q Q QC(CN) 2 ) 2 based n-channel OFETs in an integrated circuit. Thus, as a proof of concept, pseudo CMOS inverters made of n-type (2,1-b)-IF( Q Q QC(CN) 2 ) 2 -based OFETs have been fabricated and characterized highlighting the potential of this new family of materials.View Article Online † † It should be mentioned that the trend is perfectly followed as the LUMO of (2,1-b)-IF(Q Q QO) 2 lies at À2.49 eV. ‡ ‡ As depicted below, TD-DFT calculations have allowed assigning the low energy band in (2,1-b)-IF(Q Q QO) 2 , (2,1-b)-IF(Q Q QO)(Q Q QC(CN) 2 ) and (2,1-b)-IF(Q Q QC(CN) 2 ) 2 to an HOMO/LUMO transition.

The electrical stabilities of n-type Organic Field-Effect Transistors (OFETs) based on dihydroindeno[1,2-b]fluorene and dihydroindeno[2,1-b]fluorene derivatives have been studied.