Cyclodimers and Cyclotrimers of 2,3 ‐Bisalkynylated Anthracenes, Phenazines and Diazatetracenes

Abstract

The synthesis of novel (NÀ )acene-based cyclooligomers is reported. Glaser-Hay coupling of the bisethynylated monomers results in cyclodimers and cyclotrimers that are separable by column and gel-permeation chromatographies. For the diazatetracene, the use of sec-butylsilylethynyl groups is necessary to achieve solubility. Diazatetracene-based cyclodimers and cyclotrimers were used as semiconductors in thin-film transistors. Although their optoelectronic properties are quite similar, their electron mobilities in proof-of-concept thin-film transistors differ by an order of magnitude.

Second Generation of Cata‐Annulated Azaacene Bisimides: Towards Electron‐Accepting Materials

“…The compounds were drop cast (toluene 0.5 mg/ mL, 50 °C) on highly doped silicon substrates with a modified dielectric. [9,25] The dielectric consists of 100 nm SiO 2 , aluminum oxide, and 12-cyclohexyldodecylphosphonic acid [9] as a selfassembled monolayer. Changing the substituents from hexyl to phenethyl and benzyl prevented dewetting and resulted in the formation of continuous, microcrystalline films.…”

“…We demonstrated the semiconducting properties of 6 c , 7 b , and 7 c in bottom gate / top contact thin film transistors (Figure 3a). The compounds were drop cast (toluene 0.5 mg/mL, 50 °C) on highly doped silicon substrates with a modified dielectric [9,25] . The dielectric consists of 100 nm SiO 2 , aluminum oxide, and 12‐cyclohexyldodecylphosphonic acid [9] as a self‐assembled monolayer.…”

Pyrazinacene conjugated polymers: a breakthrough in synthesis and unraveling the conjugation continuum

“…With this in mind, 11 was subjected to various Sonogashira cross-coupling reaction conditions with trimethylsilylacetylene, which were unsuccessful (Table S1 †). The Bunz 48,49 group have previously used Stille cross-coupling reactions to derivatize azaacenes. Taking cues from their work, 11 was subjected to Stille cross-coupling reaction with two alkynyl stannyl derivatives (R: t-Bu; Ph) in the presence of bis(benzonitrile)palladium(II) dichloride and P(t-Bu) 3 (Scheme 1).…”

Quinoxaline-annelated hexadehydro[12]annulene: use of a new building block to construct a hydrogen-bonded hexagonal molecular network

“…The present study involved a quinoxaline-annelated hexadehydro[12]annulene derivative, because the incorporation of azaacenes, such as quinoxaline, into π-conjugated systems can provide finely tuned frontier orbital levels, 13 cation responsiveness, 14 and an environmentally responsive photophysical nature. 15 The quinoxaline-annelated [12]DBA derivative ( TQ12 ) with peripheral six carboxyphenyl groups shown in Fig.…”