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4nπ Stable Multitasking Azapentacene: Acidochromism, Hole Mobility, and Visible Light Photoresponse. | LitMetric
Herein, we describe the synthesis, characterization, and optoelectronic investigation of a stable 4nπ dihydrotetraazapentacene derivative. The neutral dihydrotetraazapentacene contains a 24π-conjugated -heteroacene core with two phenyl pendants appended thereof. The exceptional stability of this formally antiaromatic π-system is attributed to the fused dihydropyrazine ring, which has ethenamine (enamine) conjugations, and hence, the π-electrons delocalize over the nearly planar azapentacene core to endow with a global aromatic characteristic. The embedded dihydropyrazine also offers an additional Clar's sextet with enhanced aromaticity. The present dihydrotetraazapentacene can be considered as a multitasking -heteroacene, which showed photoresponsive nature under visible light illumination, acidochromism in solution, and p-type charge transport with an appreciable field-effect hole mobility of 0.02 cm V s and a bulk p-type mobility of 0.98 × 10 cm V s in the space charge-limited regime of operation measured in the hole-only device. Nucleus-independent chemical shift calculation, anisotropy of the induced current density plot, and anisotropic mobility calculation were performed to support the experimental findings.
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