Sulfur‐Containing Bent N‐Heteroacenes

Abstract

A series of novel sulfur‐containing bent N‐heteroacenes were constructed and characterized by NMR and UV/Vis spectroscopy, cyclic voltammetry, and single‐crystal X‐ray diffraction. By introducing sulfur‐containing groups (thio, sulfinyl, and sulfonyl) into bent azaacenes, their electronic delocalization was improved and frontier energy levels were modulated. The target products displayed tunable optical and electronic properties through altering the valence of sulfur and fused length of the azaacenes. For the first time, typical products were utilized as organic field effect transistor materials, affording promising results.

Towards the Bisbenzothienocarbazole Core: A Route of Sulfurated Carbazole Derivatives with Assorted Optoelectronic Properties and Applications

“…Nevertheless, in this case we found the opposite trend, i.e., the oxidation to sulfoxide leads to a noteworthy enhancement of the quantum yield with respect to the almost non-emitting sulfur derivatives. Even though there are some examples that follow this tendency [40,41], the difference between the quantum yields of both counterparts is seldom as significant as the ones herein reported. Specifically, compounds 2a and 7a, featuring the 2-methylthiophenyl unit, display low quantum yields of 0.03 and 0.05, respectively, whereas those of their oxidized analogues 2b and 7b increase to 0.34 and 0.12, respectively.…”

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

“…In addition, in order to understand the impact of different fused units, 28c fusing with a thienyl unit was also prepared in a similar manner. All compounds exhibited two reversible reduction waves with a slight increase of the first reduction waves in cyclic voltammetry as the size of the acene unit increased, and the values were also more positive relative to the corresponding non-carbonyl group-decorated species 27aa–ac and 28aa , 70,73 demonstrating their better electron accepting abilities (Fig. 6b and c).…”

Synthesis and Reactivity of Dithienopyrazines**

“…[4] Corresponding heteroacenes, which contain heteroatoms such as nitrogen or sulfur represent encouraging alternatives to the pure hydrocarbons, because electronic properties are tunable and chemical stability is typically increased. [5,6] One of the most prominent examples is represented by benzo[1,2-b : 4,5-b']dithiophene 1, which was very successfully implemented as synthon in a multitude of oligomeric [7] and polymeric materials [8] for efficient organic solar cells. However, it was found that benzodithiophenes undergo photooxidative degradation at the 4-and 8-position.…”