Ovalene’s nitrogenated derivative with all zigzag edges and nitrogen atom doping at the periphery has been developed via one-step nitrogenation of formylbisanthene. Because of nitrogen incorporation, these molecules show greatly decreased highest occupied molecular orbital levels, enhanced intermolecular interactions, and a reversible acid response. Aza-ovalene also exhibits a diatropic ring current along the periphery. This work provides rare examples of all-zigzag-edged N-polycyclic aromatic hydrocarbons.
Incorporating two pyrrole subunits at the bay positions of perylenediimide has been a long-pursued goal since 2009, but it has not been achieved due to high strain. Herein, via one step Buchwald−Hartwig reaction, PDI-2N was successfully generated with a bowl depth of 1.52 Å. Though with electron-rich pyrrole embedding, PDI-2N's radical anion and dianion were facilely prepared and were investigated both experimentally and theoretically. Moreover, PDI-2N crystallized in different manners under distinct conditions, and it formed tubular crystals with infinite two-directional columnar stacking under DMF conditions. This finding develops a dream bowl-shaped PDI derivative that holds great promise in organoelectronics.O wing to exceptional chemical, thermal, and photochemical stabilities and high fluorescence quantum yields, perylene-diimides (PDIs) (Figure 1) are among the most intensively investigated chromophores in dye chemistry. 1 Recently, numerous works have been reported modifying PDI properties by enlarging the PDI π system along the short molecular axis. This method represents a fascinating strategy, as the synthesis is usually much more straightforward compared to long-axis adjustment. More importantly, this strategy can fine-tune the electronic structures and properties of such molecules by virtue of efficient orbital−orbital coupling, nonbonding intermolecular interactions, etc. 2
In this work, nitrogen-annulated perylene (NP) was dimerized into one framework connected by two nitrogen atoms, generating the target molecule of DNPÀ DA. Owing to the substructure of 1,6-diazecine ten-membered ring, DNPÀ DA illustrates helical chirality with moderate dissymmetry factor, elevated molecular levels, expanded conjugation and supramolecular interactions with acceptors etc. Notably, DNPÀ DA represents a limited example of nitrogenÀ perylene based CPL emitter with g lum around 6 × 10 À 3 . Intrigued by the facile fabrication via a simple amination-cross coupling sequence and other above advancing features, this work demonstrates the potential generality of utilizing 1,6-diazecine as a chiral unit to build CPL-active materials.
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