10.1021/ol401375n.s001 Ning-hui Chang Ning-hui Chang Xi-chao Chen Xi-chao Chen Hikaru Nonobe Hikaru Nonobe Yasuhiro Okuda Yasuhiro Okuda Hiroki Mori Hiroki Mori Kiyohiko Nakajima Kiyohiko Nakajima Yasushi Nishihara Yasushi Nishihara Synthesis of Substituted Picenes through Pd-Catalyzed Cross-Coupling Reaction/Annulation Sequences and Their Physicochemical Properties American Chemical Society 2013 Substituted Picenes picene framework picene derivatives Physicochemical PropertiesA novel DFT calculations fluorescence spectroscopic measurements CV UV 2013-07-19 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Substituted_Picenes_through_Pd_Catalyzed_Cross_Coupling_Reaction_Annulation_Sequences_and_Their_Physicochemical_Properties/2394796 A novel and versatile synthetic method for picene derivatives is developed using the Pd-catalyzed intramolecular double cyclization of the corresponding 2,3-bis[(1<i>Z</i>)-2-phenylethenyl]-1,4-dichlorobenzenes, which are readily prepared by Suzuki–Miyaura cross-coupling reactions of polyhalobenzenes with (<i>Z</i>)-arylethenylboronates. The physical properties of the obtained picenes can be modified via introducing a variety of functional groups to the picene framework. All compounds are investigated by UV–vis and fluorescence spectroscopic measurements, CV, and DFT calculations as well as X-ray diffraction analysis.