Synthesis of metal-free organic dyes containing tris(dodecyloxy)phenyl and dithienothiophenyl units and a study of their mesomorphic and photovoltaic properties

Muthaiah Shellaiah, Hsiao Ping Fang, Yu Ling Lin, Ying Chan Hsu, Jiann T.Suen Lin, Hong-Cheu Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

In this study we synthesized three metal-free organic dyes (Cpd11, Cpd16, and Cpd22) featuring 3,4,5-tris(dodecyloxy)phenyl and cyanoacrylic acid moieties as electron-donor and electron-acceptor/anchoring units, respectively, linked through various dithienothiophenyl conjugated spacers. Cpd16 exhibits mesomorphic properties, confirmed through polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction (XRD), due to the appropriate ratio of the lengths of its flexible chain to its rigid core. Molecular modeling of Cpd16, and its d-spacing determined from XRD data, verified the existence of a tilt angle in the SmC phase. Among these metal-free organic dyes, a dye-sensitized solar cell incorporating Cpd16 exhibited the best performance, presumably because of its better packing and its mesomorphic properties; the power conversion efficiency was 3.72% (Voc=0.58 V; Jsc=9.98 mA cm-2; FF=0.65) under simulated AM 1.5 irradiation (100 mW cm-2).

Original languageEnglish
Pages (from-to)2124-2130
Number of pages7
JournalTetrahedron
Volume69
Issue number9
DOIs
StatePublished - 4 Mar 2013

Keywords

  • 3,4,5-Tris(dodecyloxy)phenyl
  • Dithienothiophene
  • Dye-sensitized solar cell
  • Metal-free organic dye

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