2026-06-28T09:42:55Zhttps://docta.ucm.es/rest/oai/request
oai:docta.ucm.es:20.500.14352/729002024-07-08T23:46:58Zcom_20.500.14352_14col_20.500.14352_15
Docta Complutense author Izquierdo García, Patricia author Fernández García, Jesús Manuel author Perles Hernáez, Josefina author Fernández López, Israel author Martín León, Nazario 2023-06-22T12:35:49Z 2023-06-22T12:35:49Z 2023 P. Izquierdo-García, J. M. Fernández-García, J. Perles, I. Fernández, N. Martín, Angew. Chem. Int. Ed. 2023, 62, e202215655; Angew. Chem. 2023, 135, e202215655. 1433-7851 10.1002/anie.202215655 https://hdl.handle.net/20.500.14352/72900 https://doi.org/10.1002/anie.202215655 https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202215655 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. eng Atribución-NoComercial 3.0 España Electronic Control of the Scholl Reaction: Selective Synthesis of Spiro vs Helical Nanographenes journal article URL https://docta.ucm.es/bitstreams/4454b418-82eb-4f20-b161-8683ba1b5ea7/download File MD5 0c19b4db920c1b96a473c90606da3f23 3370806 application/pdf Electronic_Control_of_the_Scholl_Reaction.pdf