Bromination Improves the Electron Mobility of Tetraazapentacene

Abstract

A cyclocondensation of TIPS-ethynyl-substituted diaminoarenes with in situ obtained 4,5-dibromocyclohexa-3,5-diene-1,2-dione has led to the synthesis of tetrabromotetraazapentacene (BrTAP). BrTAP is easily reduced to its air-stable radical anion and electron mobilities >0.56 cm V s can be achieved in thin-film transistors.

Regiocontrolled dimerization of asymmetric diazaheptacene derivatives toward X-shaped porous semiconductors

“…S11 †), a phenomenon observed in cellular organic semiconductors 25 and azaacene-based semiconductors. 26 Finally, we evaluated the intrinsic charge-carrier transport of the X-shaped semiconductors through single-crystal organic eld-effect transistors (SC-OFETs), which were fabricated by a "gold strips" technique. 27 The single crystals of the semiconductors were prepared by slow evaporation of the toluene solution, and they have dimensions of several mm width and hundreds of mm length (5a, Fig.…”

5,7,12,14‐Tetrafunctionalized 6,13‐Diazapentacenes

“…Herein, we describe the synthesis of tetrasubstituted 6,13‐diazapentacenes by using two different precursors. Azaacenes have aroused great interest, starting with the synthesis of the superb n‐channel semiconductor TIPS‐TAP . This interest was further stoked by new syntheses to construct azapentacenes to azaheptacenes, by using Pd‐catalyzed formation of embedded N , N′ ‐dihydropyrazines, and the availability of several privileged, bis(tri‐ iso‐ propylsilylethynyl)‐substituted aromatic ortho ‐diamines .…”

“…Azaacenes [1] have aroused great interest, startingw ith the synthesis of the superb n-channel semiconductor TIPS-TAP. [2][3][4] This interest was furthers toked by new synthesest oc onstruct azapentacenes [5] to azaheptacenes, [6] by using Pd-catalyzedf ormation of embedded N,N'-dihydropyrazines, [6,7] and the availability of several privileged, bis(tri-iso-propylsilylethynyl)-substituted aromatic ortho-diamines. [5] These approaches lead to disubstitutedazaacenes.…”

Synthesis of Tetracoordinate Boron‐Fused Benzoaceanthrylene Analogs via Tandem Electrophilic C−H Borylation

“…Furthermore, the ionization potential ( I p ) of 2‐F was determined by photoelectron spectroscopy in air to be 6.23 eV (Table ). The electron affinity ( E a ) of 2‐F was estimated from I p and the optical band gap ( E g ) to be 3.49 eV, which was larger than that of boranaphtho[1,8‐ab]perylene 1 (2.97 eV) and closer to those of reported n‐type semiconducting materials ([C60]PCBM: 3.84 eV, perylene bisimide: 3.85 eV, tetraazapentacene: 4.03 eV).…”