Bisacenaphthopyrazinoquinoxaline derivatives: synthesis, physical properties and applications as semiconductors for n-channel field effect transistors

Abstract

Several bisacenaphthopyrazinoquinoxaline (BAPQ) based derivatives 1-3 were synthesized by condensation between the acenaphthenequinones and 1,2,4,5-tetraaminobenzene tetrahydrochloride. Their optical, electrochemical and self-assembling properties are tuned by different substituents. Among them, compound 3 possesses a homogeneously distributed low-lying LUMO due to the peripheral substitution with four cyano groups. The corresponding n-channel field effect transistors showed a field effect electron mobility of 5 × 10(-3) cm(2) V(-1) s(-1).

Recent progress in pyrazinacenes containing nonbenzenoid rings: synthesis, properties and applications

“…62,64 More importantly, their inclusion often improves the electron-accepting capabilities of these molecules, 65,66 especially when combined with the electron-withdrawing effect of the pyrazine ring in azaacenes. 59 As a result, their derivatives have been proven to be potential n-type or ambipolar organic semiconductors. 67 Basically, indene/fluorene, indenone, acenaphthylene and pyracylene (Fig.…”

“…As a result, green-emitting acenaphthylene 47b showed a remarkably higher luminance (5.8 × 10 3 cd m −2 ), maximum efficiency (2.88 cd A −1 ) and efficacy (0.83 lm W −1 ) than the remaining materials. Additionally, more congeners were also synthesized by the Xiao group ( PyAP , 50 ) 90 and Chi group ( BAPQs , 51a–c ) 59 in a similar manner. Interestingly, a distinct colour change was observed in the UV/Vis absorption and fluorescence spectra of PyAP after the addition of strong protic acid, suggesting its potential application as “naked-eye” probes for protons.…”

Advantage of the N‐Alkylation Strategy for Retaining the Molecular Planarity for Oligothiophene/Imidazole/1,10‐Phenanthroline‐Based Heterocyclic Semiconducting and Fluorescent Compounds

“…In recent years, the fabrication of materials and devices at the nanometer scale through self-assembling of p-conjugated semiconducting compounds has been extensively studied in the field of molecular-based materials, [1] such as organic and polymeric light-emitting diodes, [2] field-effect transistors, [3] and photovoltaic cells. [4] The introduction of flexible, long alkyl chains into the heterocyclic aromatic system is an important strategy to obtain ordered organic materials with better optoelectronic performances.…”