Izquierdo García, PatriciaFernández García, Jesús ManuelPerles Hernáez, JosefinaFernández López, IsraelMartín León, Nazario2023-06-222023-06-222023P. Izquierdo-García, J. M. Fernández-García, J. Perles, I. Fernández, N. Martín, Angew. Chem. Int. Ed. 2023, 62, e202215655; Angew. Chem. 2023, 135, e202215655.1433-785110.1002/anie.202215655https://hdl.handle.net/20.500.14352/72900CRUE-CSIC (Acuerdos Transformativos 2022)Scholl oxidation has become an essential reaction in the bottom-up synthesis of molecular nanographenes. Herein, we describe a Scholl reaction controlled by the electronic effects on the starting substrate (1 a, b). Anthracene-based polyphenylenes lead to spironanographenes under Scholl conditions. In contrast, an electron-deficient anthracene substrate affords a helically arranged molecular nanographene formed by two orthogonal dibenzo[fg,ij]phenanthro-[9,10,1,2,3-pqrst]pentaphene (DBPP) moieties linked through an octafluoroanthracene core. Density Functional Theory (DFT) calculations predict that electronic effects control either the first formation of spirocycles and subsequent Scholl reaction to form spironanographene 2, or the expected dehydrogenation reaction leading solely to the helical nanographene 3. The crystal structures of four of the new spiro compounds (syn 2, syn 9, anti 9 and syn 10) were solved by single crystal X-ray diffraction. The photophysical properties of the new molecular nanographene 3 reveal a remarkable dual fluorescent emission.engAtribución-NoComercial 3.0 Españahttps://creativecommons.org/licenses/by-nc/3.0/es/journal articlehttps://doi.org/10.1002/anie.202215655https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202215655open accessDFT CalculationsHelically Arranged NanographenesMolecular NanographenesScholl ReactionSpironanographenesQuímica orgánica (Química)2306 Química Orgánica