Synthesis and Properties of New N-Heteroheptacenes for Solution-Based Organic Field Effect Transistors.

A series of N-heteroheptacenes was synthesized from ortho-thiophene-substituted aryl azides using a Rh -catalyzed C-H bond amination reaction to construct the thienoindole moieties. This reaction tolerated the presence of electron-donating or withdrawing groups on the aryl azide without adversely affecting the yield of the amination reaction. The central thiophene ring was created from two thienoindole pieces through a Pd-catalyzed Stille reaction to install the thioether followed by a Cu-mediated Ullman reaction to trigger the cyclization.

Synthesis and properties of semiconducting bispyrrolothiophenes for organic field-effect transistors.

A series of new highly soluble bispyrrolothiophenes were synthesized from vinyl azides by using transition-metal-catalyzed C-H-bond functionalization. In addition to modifying the substituents present on the end-pyrrolothiophene moieties, the arene linker in between the two units was also varied. The solution-state properties and field-effect-transistor (FET) electrical behavior of these bispyrrolothiophenes was compared.

BODIPY-thiophene copolymers as p-channel semiconductors for organic thin-film transistors.

The synthesis and physicochemical properties of a new class of BODIPY-based donor-acceptor π-conjugated polymers are presented. Solution-processed top-gate/bottom-contact (TG-BC) thin-film transistors on flexible plastic substrates exhibit air-stable p-channel activities with charge carrier mobilities as high as 0.17 cm(2) /V·s and current on/off ratios of 10(5) -10(6) , the highest reported to date for a BODIPY-based semiconductor.

Influence of substrate surface chemistry on the performance of top-gate organic thin-film transistors.

Organic thin-film transistor (OTFT) performance depends on the chemical characteristics of the interface between functional semiconductor/dielectric/conductor materials. Here we report for the first time that OTFT response in top-gate architectures strongly depends on the substrate chemical functionalization. Depending on the nature of the substrate surface, dramatic variations and opposite trends of the TFT threshold voltage (~±50 V) and OFF current (10(5)×!) are observed for both p- and n-channel semiconductors.

Effect of N-substituents on redox, optical, and electronic properties of naphthalene bisimides used for field-effect transistors fabrication.

Three groups of naphthalene bisimides were synthesized and comparatively studied, namely, alkyl bisimides, alkylaryl ones, and novel bisimides containing the alkylthienyl moiety in the N-substituent. The experimental absorption spectra measured in CHCl(3) exhibit one intensive absorption band that is uniformly detected in the spectral range of 340 to 400 nm for all studied molecules. This band consists of three or four vibronic peaks.