Electronic Control of the Scholl Reaction: Selective Synthesis of Spiro vs Helical Nanographenes



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Izquierdo García, Patricia and Fernández García, Jesús M. and Perles, Josefina and Fernández, Israel and Martín, Nazario (2023) Electronic Control of the Scholl Reaction: Selective Synthesis of Spiro vs Helical Nanographenes. Angewandte Chemie International Edition . ISSN 1433-7851

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Official URL: https://doi.org/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.

Item Type:Article
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CRUE-CSIC (Acuerdos Transformativos 2022)

Uncontrolled Keywords:DFT Calculations, Helically Arranged Nanographenes, Molecular Nanographenes, Scholl Reaction, Spironanographenes
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:76450
Deposited On:01 Feb 2023 11:54
Last Modified:01 Feb 2023 11:58

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