@article{oai:nagoya.repo.nii.ac.jp:02001678, author = {Odajima, Mai and Tajima, Keita and Fukui, Norihito and Shinokubo, Hiroshi}, issue = {29}, journal = {Angewandte Chemie International Edition}, month = {Jul}, note = {The synthesis and properties of dinaphthotropone bisimide (DNTrBI) and dinaphthocycloheptatriene bisimide (DNCHepBI) are described. Their molecular design is conceptually based on the insertion of a carbon atom into a perylene bisimide (PBI) core. These molecules adopt non-planar structures due to the presence of a seven-membered ring. The PBI derivative into which a carbonyl group was inserted (DNTrBI) immediately underwent nonradiative decay and/or intersystem crossing in its excited state. The PBI derivative into which a methylene group was inserted (DNCHepBI) was susceptible to deprotonation on account of the two electron-withdrawing naphthalene monoimide units. Subsequent aerobic oxidation resulted in the formation of a C−C bond at the central methylene unit, thus affording a σ-dimer. The formation of this C−C bond is dynamically redox-active, i.e., electron injection into the σ-dimer almost quantitatively regenerated the deprotonated DNCHepBI.}, pages = {15838--15843}, title = {Non‐Planar Perylene Bisimide Analogues with Inserted Carbonyl and Methylene Subunits}, volume = {60}, year = {2021} }