Xiao, Shengxiong Kang, Seok Ju Wu, Ying Ahn, Seokhoon Kim, Jong Bok Loo, Yueh-Lin Siegrist, Theo Steigerwald, Michael L. Li, Hexing Nuckolls, Colin 2024-01-20T12:32:16Z 2024-01-20T12:32:16Z 2021-09-01 2013-05 2041-6520 https://pubs.kist.re.kr/handle/201004/128143 We describe here the synthesis and electronic device properties of a new type of polycyclic aromatic molecule, the contorted octabenzocircumbiphenyl (c-OBCB). Contorted polycyclic aromatic hydrocarbons (PAHs) are promising small active molecules for organic devices. We present two different methods to synthesize c-OBCB derivatives that allow the smooth incorporation of functional groups. The material has a highly contorted exterior with six 4-helicenes and two 5-helicenes around the exterior of the expanded core of the aromatic. With appropriate sidechains, the material is soluble in common organic solvents and forms thin films. In thin films, the tetradodecyloxy-substituted c-OBCB self-assembles to form the active layer in organic field effect transistors. It is a hole transporting organic semiconductor. In the transistors, the c-OBCB forms good contact with source and drain contacts made from graphene. The c-OBCB self-assembles into a heterojunction from solution with phenyl-C-70-butyric acid methyl ester (PC70BM). We observed power conversion efficiencies of similar to 2.9% under 100 mW cm(-2) illumination at a 1 : 4 weight ratio of the c-OBCB relative to PC70BM. The c-OBCB is shape complementary to the ball shaped PC70BM. English ROYAL SOC CHEMISTRY OLEFIN SYNTHESIS HYDROCARBONS GRAPHENES Supersized contorted aromatics Article 10.1039/c3sc50374g 1 CHEMICAL SCIENCE, v.4, no.5, pp.2018 - 2023 CHEMICAL SCIENCE 4 5 2018 2023 scie scopus 000316966500011 2-s2.0-84875803124 Chemistry, Multidisciplinary Chemistry Article OLEFIN SYNTHESIS HYDROCARBONS GRAPHENES organic photovoltaics Bulkhetero junctions