title: Hybrid Corannulene-Perylene Dyes: Facile Synthesis and Optoelectronic Properties.
abstract: Considering the peculiar topology of corannulene and extraordinary optoelectronic properties of perylene dyes, a series of hybrid corannulene-perylene dyes, namely corannulene-fused perylene-3,4-dicarboxylic acid monoimide (PMI) and corannulene-fused perylene-3,4,9,10-tetracarboxylic acid diimides (PDIs), were efficiently synthesized by a Suzuki coupling (carbon-carbon bond formation) and subsequent oxidative cyclization and photocyclization, respectively. Single crystal packing demonstrates that the solid state of the corannulene-fused PMI is arranged in back to back antiparallel dimers due to the strong dipole-dipole interactions. Integration of the corannulene unit to the perylene dyes along peri-positions makes the absorption bathochromically-shifted together with a much higher molar extinction coefficient, whereas integration of the corannulene unit to the perylene dyes along bay-positions has a much broader absorption. Strong and broad absorption properties, strong electron-accepting ability, and suitable LUMO levels close to that of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) make hybrid corannulene-perylene dyes promising electron-acceptor materials for organic optoelectronic devices.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.|College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
authors.forename: Zhi
authors.initials: Z
authors.lastname: Lin
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. licheng1987@iccas.ac.cn.
authors.forename: Cheng
authors.initials: C
authors.lastname: Li
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.|University of Chinese Academy of Sciences, Beijing, 100049, China.
authors.forename: Dong
authors.initials: D
authors.lastname: Meng
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. yanli@iccas.ac.cn.
authors.forename: Yan
authors.identifier: http://orcid.org/0000-0002-5177-5418
authors.initials: Y
authors.lastname: Li
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
authors.forename: Zhaohui
authors.initials: Z
authors.lastname: Wang
keywords: corannulene; cyclization; imides; organic optoelectronic devices; perylene