Synthesis and transistor application of the extremely extended phenacene molecule, [9]phenacene

Abstract

Many chemists have attempted syntheses of extended π-electron network molecules because of the widespread interest in the chemistry, physics and materials science of such molecules and their potential applications. In particular, extended phenacene molecules, consisting of coplanar fused benzene rings in a repeating W-shaped pattern have attracted much attention because field-effect transistors (FETs) using phenacene molecules show promisingly high performance. Until now, the most extended phenacene molecule available for transistors was [8]phenacene, with eight benzene rings, which showed very high FET performance. Here, we report the synthesis of a more extended phenacene molecule, [9]phenacene, with nine benzene rings. Our synthesis produced enough [9]phenacene to allow the characterization of its crystal and electronic structures, as well as the fabrication of FETs using thin-film and single-crystal [9]phenacene. The latter showed a field-effect mobility as high as 18 cm2 V−1 s−1, which is the highest mobility realized so far in organic single-crystal FETs.

Transistor Properties of 2,7-Dialkyl-Substituted Phenanthro[2,1-b:7,8-b′]dithiophene

“…Field-effect transistors (FETs) using thin films and single crystals of phenacene-type molecules (extended W-patterned structures of fused benzene rings) have been extensively studied using various gate dielectrics123456789101112131415161718. The highest field-effect mobility ( μ ) reported in these phenacene thin-film FETs is currently 21 cm 2  V −1 s −1 .…”

“…In closely related studies, the highest μ value in a phenacene single-crystal FET is now 18 cm 2  V −1 s −1 . This was recorded in a [9]phenacene single-crystal FET, where ZrO 2 was used as the gate dielectric15. It was recently found that the μ value in a phenacene-type single-crystal FET increases as the number of benzene rings increases, i.e.…”

Toward Thiophene‐Annulated Graphene Nanoribbons

“…Thea bsorption profile of oT-GNR is very comparable to that reported by Swager et al for as imilar ladder poly(p-phenylene). [15] The slightly lower band gap of oT-GNR can be attributed to the presence of electron-rich thiophene units on the edge of the [n]phenacene backbone.R emarkably,t he solid-state absorption spectrum is only slightly broader than that in solution, meaning that very weak intermolecular p interactions take place in the solid state.U V/Vis analysis in solution showed that the spectrum of oT-GNR is concentration-independent, ruling out the possibility of aggregation in solution to explain such asimilarity between the two spectra. 3.0 eV).…”

Facile synthesis of picenes incorporating imide moieties at both edges of the molecule and their application to n-channel field-effect transistors

“…16,17 Namely, single-crystal FETs of [9]phenacene and thin-lm FETs of 3,10-ditetradecylpicene ((C 14 H 29 ) 2 -picene) displayed carrier mobility (m) as high as 18 and 21 cm 2 V À1 cm À1 , respectively. 18,19 Additionally, they have demonstrated that complementary logic circuits, such as a exible CMOS inverter by using phenacenes as p-channel materials, were realized. 20,21 In contrast to the successful developments and applications of p-channel materials, those of high-performance n-channel organic semiconductors are still a challenging task because appropriate molecular design is necessary to stabilize both the molecule and radical anion under the device operation conditions.…”