RT Journal Article
T1 Electronic Control of the Scholl Reaction: Selective Synthesis of Spiro vs Helical Nanographenes
A1 Izquierdo García, Patricia
A1 Fernández García, Jesús Manuel
A1 Perles Hernáez, Josefina
A1 Fernández López, Israel
A1 Martín León, Nazario
AB 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.
PB Wiley
SN 1433-7851
YR 2023
FD 2023
LK https://hdl.handle.net/20.500.14352/72900
UL https://hdl.handle.net/20.500.14352/72900
LA eng
NO 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.
NO CRUE-CSIC (Acuerdos Transformativos 2022)
NO Ministerio de Ciencia, Innovación y Universidades (España)
DS Docta Complutense
RD 8 abr 2025