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Optical properties of (Z)-2-(2-phenylhydrazinylidene)acenaphthen-1(2H)-one: a potential electron donor in organic

Yan Xiao Su¹, Chao Zhi Zhang¹, Ming Xia Song²

¹CICAEET, Department of Chemistry, Nanjing University of Information Science & Technology, Nanjing 210044, People's Republic of China.

Acta Crystallographica. Section C, Structural Chemistry

|June 6, 2017

Abstract:

Electron-donating molecules play an important role in the development of organic solar cells. (Z)-2-(2-Phenylhydrazinylidene)acenaphthen-1(2H)-one (PDAK), C₁₈H₁₂N₂O, was synthesized by a Schiff base reaction. The crystal structure shows that the molecules are planar and are linked together forming `face-to-face' assemblies held together by intermolecular C-H...O, π-π and C-H...π interactions. PDAK exhibits a broadband UV-Vis absorption (200-648 nm) and a low HOMO-LUMO energy gap (1.91 eV; HOMO is the highest occupied molecular orbital and LUMO is the lowest unoccupied molecular orbital), while fluorescence quenching experiments provide evidence for electron transfer from the excited state of PDAK to C₆₀. This suggests that the title molecule may be a suitable donor for use in organic solar cells.

Keywords:

acenaphthenequinone derivative broadband light absorption crystal structure electron donor low energy gap optical properties organic solar cells

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