Synthesis of 1,2,3-trisubstituted Cyclohexane and Organic Compounds for OTFTs.

Abstract

Tandem intramolecular conjugate addition is conducted with α,β-bisenones as selected Michael acceptors which are converted into 1,2,3 - trisubstituted 6-membered ring with activated oxygen and sulfur nucleophiles in good to excellent yield up to each 90.2%, 98.7% yield. Various substituted α,β-bisenones and oxygen and sulfur nucleophiles are examined to expand the scope of this chemistry. Only one diastereomer is isolated from all the following reactions because catalyst and metal additive-mediated enolate trapping protocol improves stereoselectivity of 1,2,3-trisubstituted cyclohexanes

A series of new dithieno[3,2-b:2’,3’-d]thiophene derivatives, 2,6-bis(phenylethynyl)dithieno[3,2-b:2',3'-d]thiophene (BP-Et-DTT), 2,6-bis(thiophen-2-ylethynyl)dithieno[3,2-b:2',3'-d]thiophene (BT-Et-DTT), and 2,6-bis(phenylbuta-1,3-diyn-1-yl)dithieno[3,2-b:2',3'-d]thiophene (BP-Bd-DTT), were synthesized and characterized as solution-processable organic semiconductors for organic thin-film transistors (OTFTs) and complementary-like inverter applications. Thermal, optical, and electrochemical properties of the new compounds were investigated. The solution-sheared thin films based on new compounds exhibited p-type characteristics as an active layer in organic thin-film transistors. The highest hole mobility was 0.14 cm2 V−1s−1 based on BP-Et-DTT thin films. Furthermore, bulk heterojunction (BHJ) ambipolar transistors with balanced hole (0.011 cm2 V−1s−1) and electron mobility (0.013 cm2 V−1s−1) were fabricated with an optimized blending ratio of BP-Et-DTT and the representative n-type semiconductor, PDIFCN2. Complementary-like inverters were fabricated based on the two identical ambipolar transistors resulting in voltage gains of up to 16.