1‐Aryl‐4‐Silylmethyl[60]fullerenes: Synthesis, Properties, and Photovoltaic Performance. Issue 1 (28th September 2012)

• Record Type: Journal Article
• Authors: Matsuo, Yutaka; Oyama, Hiromi; Soga, Iwao; Okamoto, Toshihiro; Tanaka, Hideyuki; Saeki, Akinori; Seki, Shu; Nakamura, Eiichi
• Is Part Of: Chemistry, an Asian journal. Volume 8:Issue 1(2013:Jan.)
• Page Start: 121
• Page End: 128
• Publication Date: 2012-09-28
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201200726
• Languages: English
• ISSNs: 1861-4728

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The efficient nucleophilic addition of aryl Grignard reagents (aryl=4‐MeOC₆H₄, 4‐Me₂NC₆H₄, Ph, 4‐CF₃C₆H₄, and thienyl) to C₆₀ in the presence of DMSO produced 1, 2‐arylhydro[60]fullerenes after acid treatment. The reactions of the anions of these arylhydro[60]fullerenes with either dimethylphenylsilylmethyl iodide or dimethyl(2‐isopropoxyphenyl)silylmethyl iodide yielded the target compounds, 1‐aryl‐4‐silylmethyl[60]fullerenes. The properties and structures of these 1‐aryl‐4‐silylmethyl[60]fullerenes (aryl=4‐MeOC₆H₄, thienyl) were examined by electrochemical studies, X‐ray crystallography, flash‐photolysis time‐resolved microwave‐conductivity (FP‐TRMC) measurements, and electron‐mobility measurements by using a space‐charge‐limited current (SCLC) model. Organic photovoltaic devices with a polymer‐based bulk heterojunction structure and small‐molecule‐based <italic>p–n</italic> and <italic>p</italic>–<italic>i</italic>–<italic>n</italic> heterojunction configurations were fabricated by using 1‐aryl‐4‐silylmethyl[60]fullerenes as an electron acceptor. The most efficient device exhibited a power‐conversion efficiency of 3.4 % (short‐circuit current density: 8.1 mA/ cm², open‐circuit voltage: 0.69 V, fill factor: 0.59).</p> </abstract>